A straightforward metal-free synthesis of 2-substituted thiazolines in air
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- Σωτηρία Μακρή
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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for A straightforward metal-free synthesis of 2-substituted thiazolines in air Michael Trose, Faïma Lazreg, Mathieu Lesieur and Catherine S. J. Cazin* School of Chemistry University of St Andrews, St Andrews, KY16 9ST, United Kingdom Fax: (+) 44 (0) ; cc111@st-andrews.ac.uk S1
2 Table of Contents 1 General considerations... S5 2 Optimisation of reaction conditions... S5 3 In Situ FTIR Spectroscopy... S7 IR spectra of benzonitrile, 1a... S7 IR spectra of 2-Phenyl-4,5-dihydrothiazole, 4a... S7 Reaction between benzonitrile and cysteamine hydrochloride without base... S8 Reaction between benzonitrile and cysteamine hydrochloride in the presence of NaOH... S10 4 Synthesis and characterisation of thiazolines... S11 2-Phenyl-4,5-dihydrothiazole, 4a... S11 2-(4-Fluorophenyl)-4,5-dihydrothiazole, 4b... S11 2-(4-Chlorophenyl)-4,5-dihydrothiazole, 4c... S12 2-(4-Bromophenyl)-4,5-dihydrothiazole, 4d... S12 2-p-Tolyl-4,5-dihydrothiazole, 4e... S12 2-(4-Methoxyphenyl)-4,5-dihydrothiazole, 4f... S13 4-(4,5-Dihydrothiazol-2-yl)aniline, 4g... S13 2-(3-Bromophenyl)-4,5-dihydrothiazole, 4h... S13 2-m-Tolyl-4,5-dihydrothiazole, 4i... S14 3-(4,5-Dihydrothiazol-2-yl)aniline, 4j... S14 2-(3,5-Difluorophenyl)-4,5-dihydrothiazole, 4k... S14 2-(2-Chlorophenyl)-4,5-dihydrothiazole, 4l... S15 2-(2-Bromophenyl)-4,5-dihydrothiazole, 4m... S15 2-(4,5-Dihydrothiazol-2-yl)aniline, 4n... S15 2-(4-Chlorobenzyl)-4,5-dihydrothiazole, 4o... S16 2-Benzyl-4,5-dihydrothiazole, 4p... S16 2-(2-Bromobenzyl)-4,5-dihydrothiazole, 4q... S16 2-(Pyridin-2-yl)-4,5-dihydrothiazole, 4r... S16 2-(Pyridin-3-yl)-4,5-dihydrothiazole, 4s... S17 2-(Pyridin-4-yl)-4,5-dihydrothiazole, 4t... S17 2-(1H-Pyrrol-2-yl)-4,5-dihydrothiazole, 4u... S17 2-(2-Furanyl)-4,5-dihydrothiazole, 4v... S18 2-(Pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w... S18 2-Pentyl-4,5-dihydrothiazole, 4x... S18 2-Cyclohexyl-4,5-dihydrothiazole, 4y... S19 5 NMR spectra... S20 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-phenyl-4,5-dihydrothiazole, 4a... S20 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-phenyl-4,5-dihydrothiazole, 4a... S20 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b... S21 S2
3 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b... S21 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b... S22 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c... S23 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c... S23 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d... S24 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d... S24 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-p-tolyl-4,5-dihydrothiazole, 4e... S25 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-p-tolyl-4,5-dihydrothiazole, 4e... S25 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f... S26 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f... S26 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g... S27 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g... S27 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h... S28 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h... S28 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-m-tolyl-4,5-dihydrothiazole, 4i... S29 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-m-tolyl-4,5-dihydrothiazole, 4i... S29 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j... S30 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j... S30 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k... S31 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k... S31 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k... S32 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l... S33 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l... S33 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m... S34 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m... S34 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n... S35 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n... S35 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o... S36 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o... S36 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-benzyl-4,5-dihydrothiazole, 4p... S37 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-benzyl-4,5-dihydrothiazole, 4p... S37 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q... S38 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q... S38 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r... S39 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r... S39 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s... S40 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s... S40 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t... S41 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t... S41 S3
4 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u... S42 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u... S42 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v... S43 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v... S43 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w... S44 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w... S44 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-pentyl-4,5-dihydrothiazole, 4x... S45 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-pentyl-4,5-dihydrothiazole, 4x... S45 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-cyclohexyl-4,5-dihydrothiazole, 4y... S46 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-cyclohexyl-4,5-dihydrothiazole, 4y... S46 6 References... S47 S4
5 1 General considerations All reactions were carried out in air. All reagents were purchased and used as received. 1 H, 13 C-{ 1 H} and 19 F-{ 1 H} Nuclear Magnetic Resonance (NMR) spectra were recorded at 298K on a Brucker Avance 400 Ultrashield or on a Brucker Avance 500 Ultrashield spectrometer using the residual solvent peak for 13 C-{ 1 H} NMR (CDCl 3: δ C = ppm) and TMS as reference for 1 H NMR. Gas chromatography (GC) analyses were performed on an Agilent 7890A apparatus equipped with a flame ionization detector and a (5%-phenyl)-methylpolysiloxane column (30 m, 320 μm, film: 0.25 μm). IR measurements were performed on a ReactIR A15 system (Mettler Toledo Autochem) with a DiComp AgX FiberConduit probe (9.5 mm). Mass spectroscopy was performed by the EPSRC National Mass Spectrometry Service Centre at Swansea University, UK. 2 Optimisation of reaction conditions Table S1. Optimisation of reaction conditions N NH HS 3 1a 3 Cl Base 80 C, 16 h N S 4a Entry 3 (mmol) Base (Loading) Time (h) Conversion (%) 1 1 NaOH (30 mol%) 16 > NaOH (20 mol%) 16 > NaOH (10 mol%) 16 > CsOH (10 mol%) 16 > KOH (10 mol%) 16 > NaOH (5 mol%) NaOH (20 mol%) 16 > NaOH (20 mol%) 2 > 99 (98) c NaOH (20 mol%) 1 94 a Reaction conditions: 1 (0.5 mmol), 3 ( mmol), base-catalyst, 80 ºC, 1-16h. b Conversion determined by GC, based on benzonitrile, average of 2 reactions. c Isolated yield. S5
6 Table S2. Comparison of sources of NaOH a N NH HS 3 1a 3 Cl NaOH 20 mol% 80 C, 2 h N S 4a Entry Base Conversion b (%) 1 NaOH batch1 > 99 2 NaOH batch2 > 99 3 NaOH batch3 > 99 4 NaOH semiconductor grade > 99 a Reaction conditions: 1 (0.5 mmol), 3 (0.75 mmol), NaOH (20 mol%), 80 ºC, 2h. b Conversion determined by GC, based on benzonitrile, average of 2 reactions. S6
7 3 In Situ FTIR Spectroscopy Figure S1 IR spectra of benzonitrile, 1a Figure S2 IR spectra of 2-Phenyl-4,5-dihydrothiazole, 4a S7
8 Reaction between benzonitrile and cysteamine hydrochloride without base PROCEDURE: In air, a 5 ml round bottom flask was charged with benzonitrile (19.4 mmol, 2.0 g) and cysteamine hydrochloride (29.1 mmol, 3.3 g). The mixture was heated at 80 C until cysteamine hydrochloride was completely melted. The probe was submerged in the reaction mixture and the IR measurements were started. The reaction was stirred (350 rpm) at 80 C for 1h under solvent-free conditions. Figure S3 3D plot of in situ IR measurements of the reaction between 1a and 3 without base. S8
9 Figure S4 IR plot of the reaction between 1a and 3 without base. S9
10 Reaction between benzonitrile and cysteamine hydrochloride in the presence of NaOH PROCEDURE: In air, a 5 ml round bottom flask was charged with benzonitrile (19.4 mmol, 2.0 g) and cysteamine hydrochloride (29.1 mmol, 3.3 g). The mixture was heated at 80 C until cysteamine hydrochloride was completely melted. The probe was submerged inside of the reaction mixture and the IR measurements were started. After 5 minutes 20 mol % of NaOH (2 mmol, 80 mg) were added. The reaction was stirred (350 rpm) at 80 C for 1h under solvent-free conditions. Figure S5 3D plot of in situ IR measurements of the reaction between 1a and 3 in the presence of NaOH. S10
11 Figure S6 IR plot of the reaction between 1a and 3 in the presence of NaOH. 4 Synthesis and characterisation of thiazolines In air, a vial was charged with the nitrile (1 mmol), cysteamine hydrochloride (1.5 mmol) and NaOH (0.2 mmol). The reaction was stirred at 80 C for the appropriate time under solvent-free conditions. The crude product was dissolved in ethyl acetate (2 ml) and water (10 ml) was added. The aqueous layer was then extracted with ethyl acetate (3 x 10 ml). The combined organic layers were dried over MgSO 4, filtered and dried under vacuum to give the desired compound. The conversion was determined by GC analysis or by 1 H NMR. 2-Phenyl-4,5-dihydrothiazole, 4a [1] The general procedure yielded to the title compound as a yellow oil (153 mg, 98%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 3H, C ArH) 4.45 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.40 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), 65.5 (s, CH 2), 33.9 (s, CH 2). 2-(4-Fluorophenyl)-4,5-dihydrothiazole, 4b [2] The general procedure yielded to the title compound as a colourless oil (168 mg, 93%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.41 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.3 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (d, 1 J CF= Hz, C IV ), (d, 4 J CF= 8.7 Hz, C ArH), (d, 5 J CF= 3.6 Hz, C IV ), (d, 3 J CF= 22.2 Hz, C ArH), 65.3 (s, CH 2), 34.0 (s, CH 2). S11
12 19 F-{ 1 H} NMR (376 MHz, 298K): δ (ppm) = (s, CF). 2-(4-Chlorophenyl)-4,5-dihydrothiazole, 4c [1] The general procedure yielded to the title compound as a colourless solid (179 mg, 91%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), (m, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), 65.6 (s, CH 2), 34.2 (s, CH 2). Melting point: 53 C 2-(4-Bromophenyl)-4,5-dihydrothiazole, 4d [3] The general procedure yielded to the title compound as a colourless solid (228 mg, 94%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.44 (t, 3 J HH = 8.4 Hz, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C IV ), 65.6 (s, CH 2), 34.3 (s, CH 2). Melting point: 91 C 2-p-Tolyl-4,5-dihydrothiazole, 4e [1] The general procedure yielded to the title compound as a colourless solid (158 mg, 89%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.43 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 2.37 (s, 3H, CH 3). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), 65.4 (s, CH 2), 33.9 (s, CH 2), 21.7 (s, CH 3). Melting point: 42 C S12
13 2-(4-Methoxyphenyl)-4,5-dihydrothiazole, 4f [3] The general procedure yielded to the title compound as a yellow solid (188 mg, 97%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.39 (t, 3 J HH = 8.2 Hz, 2H, CH 2), 3.80 (s, 3H, OCH 3), 3.35 (t, 3 J HH = 8.2 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C IV ), (s, C ArH), 65.2 (s, CH 2), 55.5 (s, OCH 3), 33.8 (s, CH 2). Melting point: 53 C 4-(4,5-Dihydrothiazol-2-yl)aniline, 4g [4] The general procedure yielded to the title compound as a pale yellow oil (166 mg, 93%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), (m, 2H, CH 2), 3.98 (s, 2H, NH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C IV ), (s, C ArH), 65.1 (s, CH 2), 33.7 (s, CH 2). 2-(3-Bromophenyl)-4,5-dihydrothiazole, 4h [5] The general procedure yielded to the title compound as a pale brown solid (226 mg, 94%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 8.00 (d, 5 J HH = 1.9 Hz, 1H, C ArH), 7.72 (dt, 3 J HH = 7.8 Hz, 5 J HH = 1.4 Hz, 1H, C ArH), 7.57 (dq, 3 J HH = 7.8 Hz, 5 J HH = 1.2 Hz, 1H, C ArH), 7.26 (t, 3 J HH = 7.8 Hz, 1H, C ArH), 4.44 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.42 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 122.8(s, C IV ), 65.5 (s, CH 2), 34.2 (s, CH 2). Melting point: 45 C S13
14 2-m-Tolyl-4,5-dihydrothiazole, 4i [6] The general procedure yielded to the title compound as a colourless oil (150 mg, 85%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.67 (s, 1H, C ArH), 7.62 (d, 3 J HH = 7.3 Hz, 1H, C ArH), (m, 2H, C ArH), 4.43 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 2.38 (s, 3H, CH 3). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.4 (s, CH 2), 33.8 (s, CH 2), 21.5 (s, CH 3). 3-(4,5-Dihydrothiazol-2-yl)aniline, 4j [1] The general procedure yielded to the title compound as a brown solid (176 mg, 99%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 3H, C ArH), (m, 1H, C ArH), 4.40 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.79 (s, 2H, NH 2), 3.35 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.2 (s, CH 2), 33.7 (s, CH 2). Melting point: 66 C 2-(3,5-Difluorophenyl)-4,5-dihydrothiazole, 4k The general procedure yielded to the title compound as a colourless solid (194 mg, 98%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 1H, C ArH), 4.46 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.45 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (m, C IV ), (dd, 1 J CF= Hz, 3 J CF= 14.2 Hz, C IV ), (t, 3 J CF= 10.2 Hz, C IV ), (dd, 2 J CF= 19.7 Hz, 4 J CF= 7.9 Hz, C ArH), (t, 2 J CF= 25.6 Hz, C ArH), 65.5 (s, CH 2), 34.4 (s, CH 2). 19 F-{ 1 H} NMR (376 MHz, 298K): δ (ppm) = (s, CF). HRMS calcd. for C9H8F2NS (M+H) found Melting point: 43 C S14
15 2-(2-Chlorophenyl)-4,5-dihydrothiazole, 4l [1] The general procedure yielded to the title compound as a light yellow oil (180 mg, 91%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.60 (dd, 3 J HH = 7.6 Hz, 5 J HH = 1.8 Hz, 1H, C ArH), 7.42 (dd, 3 J HH = 7.9 Hz, 5 J HH = 1.2 Hz, 1H, C ArH), 7.32 (td, 3 J HH = 7.4 Hz, 5 J HH 1.8 Hz, 1H, C ArH), 7.27 (td, 3 J HH = 7.6 Hz, 5 J HH = 1.4 Hz,1H, C ArH), 4.46 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.44 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.3 (s, CH 2), 34.9 (s, CH 2). 2-(2-Bromophenyl)-4,5-dihydrothiazole, 4m The general procedure yielded to the title compound as a colourless oil (234 mg, 98%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.60 (dd, 3 J HH = 8.0 Hz, 5 J HH = 1.1 Hz, 1H, C ArH), 7.52 (dd, 3 J HH = 7.6 Hz, 5 J HH = 1.8 Hz, 1H, C ArH), 7.31 (td, 3 J HH = 7.6 Hz, 5 J HH = 1.2 Hz, 1H, C ArH), 7.22 (td, 3 J HH = 8.0 Hz, 5 J HH = 1.8 Hz, 1H, C ArH), 4.46 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.45 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), 65.4 (s, CH 2), 35.1 (s, CH 2). HRMS calcd. for C9H9BrNS (M+H) found (4,5-Dihydrothiazol-2-yl)aniline, 4n [1] The general procedure yielded to the title compound as a pale yellow oil (176 mg, 99%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.47 (d, 3 J HH = 8.0 Hz, 1H, C ArH), 7.16 (t, 3 J HH = 7.5 Hz, 1H, C ArH), (m, 2H, C ArH), 6.17 (s, 2H, NH 2), (m, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), 65.5 (s, CH 2), 32.1 (s, CH 2). S15
16 2-(4-Chlorobenzyl)-4,5-dihydrothiazole, 4o [1] The general procedure yielded to the title compound as a yellow oil (194 mg, 92%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.28 (d, 3 J HH = 8.4 Hz, 2H, C ArH), 7.21 (d, 3 J HH = 8.4 Hz, 2H, C ArH), 4.23 (t, 3 J HH = 8.4 HZ, 2H, CH 2), 3.77 (s, 2H, CH 2), 3.26 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), 64.9 (s, CH 2), 40.3 (s, CH 2), 34.5 (s, CH 2). 2-Benzyl-4,5-dihydrothiazole, 4p [1] The general procedure yielded to the title compound as a yellow oil (172 mg, 97%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 5H, C ArH), (m, 2H, CH 2), 3.78 (s, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), 64.6 (s, CH 2), 40.7 (s, CH 2), 34.1 (s, CH 2). 2-(2-Bromobenzyl)-4,5-dihydrothiazole, 4q The general procedure yielded to the title compound as a colourless oil (232 mg, 91%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.54 (d, 3 J HH = 7.5 Hz, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), 4.21 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.95 (s, 2H, CH 2), 3.24 (t, 3 J HH = 8.3 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), 64.8 (s, CH 2), 40.8 (s, CH 2), 34.2 (s, CH 2). HRMS calcd. for C10H11BrNS (M+H) found (Pyridin-2-yl)-4,5-dihydrothiazole, 4r [1] The general procedure yielded to the title compound as a colourless solid (159 mg, 97%). S16
17 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 8.66 (s, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), (m, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.9 (s, CH 2), 32.7 (s, CH 2). Melting point: 92 C 2-(Pyridin-3-yl)-4,5-dihydrothiazole, 4s [1] The general procedure yielded to the title compound as a yellow oil (158 mg, 96%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 9.04 (d, 5 J HH 1.6 Hz, 1H, C ArH), 8.68 (dd, 3 J HH = 4.8 Hz, 5 J HH = 1.6 Hz, 1H,C ArH), 8.10 (dt, 3 J HH = 8.0 Hz, 5 J HH = 1.9 Hz, 1H, C ArH), 7.35 (dd, 3 J HH = 8.0 Hz, 5 J HH = 4.8 Hz, 1H, C ArH), 4.46 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.45 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), (s, C ArH), 65.2 (s, CH 2), 33.9 (s, CH 2). 2-(Pyridin-4-yl)-4,5-dihydrothiazole, 4t [1] The general procedure yielded to the title compound as a colourless solid (157 mg, 96%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 8.70 (dd, 3 J HH = 4.5 Hz, 5 J HH = 1.7 Hz, 2H, C ArH), 7.67 (dd, 3 J HH = 4.5 Hz, 5 J HH = 1.7 Hz, 2H, C ArH), 4.50 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.47 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C ArH), (s, C IV ), (s, C ArH), 65.7 (s, CH 2), 34.2 (s, CH 2). Melting point: 73 C 2-(1H-Pyrrol-2-yl)-4,5-dihydrothiazole, 4u [7] The general procedure yielded to the title compound as a colourless solid (300 mg, 98%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (s, 1H, NH), 6.90 (s, 1H, C ArH), 6.64 (d, 3 J HH = 2.9 Hz, 1H, C ArH), 6.23 (t, 3 J HH = 2.9 Hz, 1H, C ArH), 4.35 (t, 3 J HH = 8.1 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.1 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), 64.1 (s, CH 2), 33.7 (s, CH 2). S17
18 Melting point: 94 C 2-(2-Furanyl)-4,5-dihydrothiazole, 4v [6] The general procedure yielded to the title compound as a yellow oil (291 mg, 95%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 1H, C ArH), 6.88 (d, 3 J HH = 3.5 Hz, 1H, C ArH), 6.46 (dd, 3 J HH = 3.5 Hz, 5 J HH 1.8 Hz, 1H, C ArH), 4.37 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.34 (t, 3 J HH = 8.3 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (C ArH), (C ArH), 64.5 (s, CH 2), 33.1 (s, CH 2). 2-(Pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w The general procedure yielded to the title compound as a colourless oil (132 mg, 87%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, CH 2), (m, 2H, CH 2), (m, 2H, CH 2), (m, 2H, CH 2), (m, 1H, CH), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), 83.6 (s, CH), 69.3 (s, C IV ), 64.8 (s, CH 2), 34.0 (s, CH 2), 33.2 (s, CH 2), 26.3 (s, CH 2), 18.1 (s, CH 2). HRMS calcd. for C8H12NS (M+H) found Pentyl-4,5-dihydrothiazole, 4x [8] The general procedure yielded after flash chromatography (SiO 2, penthane/ ethyl acetate 7:3) to the title compound as a colourless oil (85 mg, 55%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 4.21 (tt, 3 J HH = 8.4 Hz, 5 J HH = 1.4 Hz, 2H, CH 2), 3.27 (t, 3 J HH = 8.4 Hz, 2H, CH 2), (m, 2H, CH 2), (m, 2H, CH 2), (m, 4H, CH 2), (m, 3H, CH 3). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), 64.8 (s, CH 2), 34.6 (s, CH 2), 34.0 (s, CH 2), 31.6 (s, CH 2), 27.5 (s, CH 2), 22.6 (s, CH 2), 14.2 (s, CH 3). HRMS calcd. for C8H16NS (M+H) found S18
19 2-Cyclohexyl-4,5-dihydrothiazole, 4y [8] The general procedure yielded after flash chromatography (SiO 2, penthane/ ethyl acetate 8:2) to the title compound as a colourless oil (77 mg, 45%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 4.20 (td, 3 J HH = 8.4 Hz, 5 J HH = 1.1 Hz, 2H, CH 2), 3.22 (t, 3 J HH = 8.4 Hz, 2H, CH 2), (m, 1H, CH), (m, 2H, CH 2), (m, 2H, CH 2), (m, 1H, CH 2), (m, 5H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), 64.7 (s, CH 2), 43.6 (s, CH), 33.3 (s, CH 2), 31.8 (s, CH 2), 26.2 (s, CH 2). S19
20 5 NMR spectra 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-phenyl-4,5-dihydrothiazole, 4a 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-phenyl-4,5-dihydrothiazole, 4a S20
21 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b S21
22 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b S22
23 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c S23
24 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d S24
25 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-p-tolyl-4,5-dihydrothiazole, 4e 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-p-tolyl-4,5-dihydrothiazole, 4e S25
26 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f S26
27 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g S27
28 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h S28
29 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-m-tolyl-4,5-dihydrothiazole, 4i 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-m-tolyl-4,5-dihydrothiazole, 4i S29
30 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j S30
31 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k S31
32 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k S32
33 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l S33
34 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m S34
35 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n S35
36 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o S36
37 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-benzyl-4,5-dihydrothiazole, 4p 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-benzyl-4,5-dihydrothiazole, 4p S37
38 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q S38
39 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r S39
40 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s S40
41 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t S41
42 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u S42
43 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v S43
44 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w S44
45 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-pentyl-4,5-dihydrothiazole, 4x 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-pentyl-4,5-dihydrothiazole, 4x S45
46 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-cyclohexyl-4,5-dihydrothiazole, 4y 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-cyclohexyl-4,5-dihydrothiazole, 4y S46
47 6 References [1] X. Li, B. Zhou, J. Zhang, M. She, S. An, H. Ge, C. Li, B. Yin, J. Li and Z. Shi, Eur. J. Org. Chem. 2012, 8,1626. [2] L. Wu, E-Journal of Chemistry, 2012, 9, [3] U. Pathak, S. Bhattacharyya, V. Dhruwansh, L. K. Pandey, R. Tank and M. V. S. Suryanarayana, Green Chem., 2011, 13, 1648 [4] S. H. Babcock and R. Adams, J. Am. Chem. Soc., 1937, 59, [5] S. F. Hojati, I. Mohammadpoor-Baltork, B. Maleki, M. Gholizadeh, F. Shafiezadeh and M. Haghdous, Can. J. Chemistry, 2010, 88, 135. [6] J. A. Seijas, M. P. Vázquez-Tato, J. Crecente-Campo, Tetrahedron, 2008, 64, [7] B. George, E. P. Papadopoulos, J. Org. Chem., 1977, 42, 441. [8] A. I. Meyers and J. L. Durandetta, J. Org. Chem., 1975, 40, S47
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Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and
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