Vilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides
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- Ἰωήλ Χριστόπουλος
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Vilsmeier aack reagent-promoted formyloxylation of α-chloro-arylacetamides by formamide Jiann-Jyh uang, a,b Shi-an Lu, c Yu suan Chung, a,b and Fung Fuh Wong* c a Department of Applied Chemistry, ational Chiayi University, o. 300, Syuefu Rd., Chiayi City 60004, Taiwan b Center of Energy Research & Sensor Technology, ational Chiayi University, o. 300, Syuefu Rd., Chiayi City 60004, Taiwan c School of Pharmacy, China Medical University, o. 9, sueh-shih Rd., Taichung 40402, Taiwan *Corresponding Author. Tel.: ext. 5603; Fax: address: wongfungfuh@yahoo.com.tw, ffwong@mail.cmu.edu.tw (F. F. Wong) Keywords: Vilsmeier aack reagent, formyloxylation, formate ester, formamide, phosphorous bromide, α-formyloxy--arylacetamide All chemicals were reagent grade and used as purchased. All reactions were carried out under argon or nitrogen atmosphere and monitored by TLC. Flash column chromatography was carried out on silica gel ( mesh). Analytical thin-layer chromatography (TLC) was performed on precoated plates (silica gel 60 F-254) purchased from Merck Inc. Mixtures of ethyl acetate and hexanes were used as eluants. Infrared (IR) spectra were measured on a Bomem Michelson Series FT-IR spectrometer. The wavenumbers reported are referenced to the polystyrene absorption at 60 cm. Absorption intensities are recorded by the following abbreviations: s, strong; m, medium; w, weak. Proton MR spectra were obtained on a Bruker (200 Mz or 500 Mz) spectrometer by use of CDCl 3 as solvent. Multiplicities are recorded by the following abbreviations: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; J, coupling constant (z). Carbon- MR spectra were obtained on a - -
2 Bruker (50 Mz or 25 Mz) spectrometer by used of CDCl 3 as solvent. Carbon- chemical shifts are referenced to the center of the CDCl 3 triplet (δ 77.0 ppm). ighresolution mass spectra were obtained from a JEL JMS-X0 mass spectrometer. General procedure for the formyloxylation of α-chloro--arylacetamides, 6a n, 8a, 8b, and 8c with formamide in the presence of PBr 3. α-chloro--arylacetamides, 6a n, 8a, 8b, and 8c (~.0 mmol,.0 equiv) were dissolved in formamide (2.0 ml) and added with PBr 3 (3.0 equiv). The reaction mixture was heated at C for 4.0 h. The solution was added with saturate aqueous ac 3 (5 ml) and extracted with C 2 Cl 2 (5 ml 2). The combined organic layers were washed with saturated aqueous ac 3 (5 ml), dried over MgS 4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding α-formyloxylated products 4, 7a n, 9a, and 9c in 70 96% yields. 2-xo-2-(phenylamino)ethyl formate (4). Yield: 96%; yellow liquid; MR (CDCl 3, 200 Mz) δ 4.72 (s, 2, C 2 ), (m,, Ar), (dd, J = 8.2, 7.8 z, 2, Ar), 7.5 (d, J = 8.2 z, 2, Ar), 8.02 (br,, ), 8.4 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.36, 20.9, 25.5, 29.6, 7.04, (C=), 64. (C=); IR (KBr) 3298 (br, ), 306, 730 (s, C=), 680 (s, C=), 63, 759 cm ; EIMS m/z 79 (M +, 43), 20 (7), 93 (00), 92 (7), 77 (24), 65 (20), 5 (6); RMS Calcd for C : ; Found: [(2-Fluorophenyl)amino]-2-oxoethyl formate (7a). Yield: 74%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.79 (s, 2, C 2 ), (m, 4, Ar), 8.20 (s,, =C ), 8.29 (br,, ); C MR (CDCl 3, 50 Mz) δ 62.3, 4.8, 5.8, 2.9, 24.75, 25.20, 25.33, 50.88, 54.97, (C=), (C=); IR (KBr) 3275 (br, ), 732 (s, C=), 685 (s, C=), 458, 6 (C ), 756 cm ; EIMS m/z 97 (M +, 26), (00), 83 (5), 0 (0), 57 (5); - 2 -
3 RMS Calcd for C 9 8 F 3 : ; Found: [(3-Fluorophenyl)amino]-2-oxoethyl formate (7b). Yield: 84%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.75 (s, 2, C 2 ), (m,, Ar), (m, 2, Ar), 7.44 (dd, J = 0.7, 3.5 z,, Ar), 8.02 (br,, ), 8.7 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.7, 07.44, 07.96,.64, 2.06, 5.40, 0., 0.3, 7.89, 8.0, (C=), 60.4, (C=), 65.29; IR (KBr) 3290 (br, ), 732 (s, C=), 68 (s, C=), 543, 57 (C ), 775 cm ; EIMS m/z 97 (M +, 40), 8 (2), (00), 0 (6), 95 (6), 84 (), 83 (9), 57 (8); RMS Calcd for C 9 8 F 3 : ; Found: [(4-Fluorophenyl)amino]-2-oxoethyl formate (7c). Yield: 88%; white solids; mp 49 5 C; MR (CDCl 3, 200 Mz) δ 4.76 (s, 2, C 2 ), (m, 2, Ar), (m, 2, Ar), 7.8 (br,, ), 8.9 (s,, =C ); C MR (CDCl 3, 25 Mz) δ 62.3, 5.80, 5.98, 22.06, 22.2, 2.5, 58.75, (C=), 60.58, 64.6 (C=); IR (KBr) 3336 (br, ), 2924, 735 (s, C=), 68 (s, C=), 52, 57 (C ) cm ; EIMS m/z 97 (M +, 40), 8 (2), (00), 0 (6), 95 (6), 84 (), 83 (9), 57 (8); RMS Calcd for C 9 8 F 3 : ; Found: [(2-Bromophenyl)amino]-2-oxoethyl formate (7d). Yield: 7%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.80 (s, 2, C 2 ), 6.99 (dd, J = 7.8, 7.2 z,, Ar), 7.30 (dd, J = 7.8, 7.2 z,, Ar), 7.53 (dd, J = 7.7, 6.0 z,, Ar), 8.22 (s,, =C ), 8.32 (dd, J = 7.7, 6.0 z,, Ar), 8.43 (br,, ); C MR (CDCl 3, 50 Mz) δ 62.30,.60, 2.84, 25.89, 28.49, 2.32, 4.49, (C=), (C=); IR (KBr) 3375 (br, ), 735 (s, C=), 53 (s, C=), 438, 57 (C ), 582 cm ; EIMS m/z 259 (M + + 2, ), 257 (M +, ), 73 (57), 7 (59); RMS Calcd for C 9 8 Br 3 : ; Found: [(3-Bromophenyl)amino]-2-oxoethyl formate (7e). Yield: 78%; yellow liquid; - 3 -
4 MR (CDCl 3, 200 Mz) δ 4.75 (s, 2, C 2 ), (m,, Ar), 7.4 (dd, J = 9.8, 7.5 z, 2, Ar), 7.77 (s,, Ar), 8.7 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.2, 8.59, 22.67, 23.06, 28.2, 0.4, 7.72, 58.8 (C=), (C=); IR (KBr) 3305 (br, ), 732 (s, C=), 682 (s, C=), 423, 6 (C ), 590 cm ; EIMS m/z 259 (M + + 2, 8), 257 (M +, 8), 23 (57), 229 (58), 200 (20), 98 (20), 73 (92), 7 (00); RMS Calcd for C 9 8 Br 3 : ; Found: [(4-Bromophenyl)amino]-2-oxoethyl formate (7f). Yield: 89%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.73 (s, 2, C 2 ), (m, 4, Ar), 8.03 (br,, ) 8.5 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.4, 7.76, 2.7 (2 C), 2.04 (2 C), 5.57, (C=), (C=); IR (KBr) 3433 (br, ), 732 (s, C=), 689 (s, C=), 26, 6 (C ), 574 cm ; EIMS m/z 259 (M + + 2, 6), 257 (M +, 6), 9 (00), 78 (25), 73 (33), 7 (33), 52 (), 9 (7); RMS Calcd for C 9 8 Br 3 : ; Found: xo-2-{[2-(trifluoromethyl)phenyl]amino}ethyl formate (7g). Yield: 70%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.80 (s, 2, C 2 ), (m,, Ar), (m, 2, Ar), 8.9 (s,, =C ), (m,, Ar), 8.25 (br,, ); C MR (CDCl 3, 50 Mz) δ 62.9, 9.98, 20.20, 20.58, 20.87, 2.20, 24.08, 25.4, 26.27, 26.63, 3.08, 3.93, (C=), (C=); IR (KBr) 3433 (br, ), 72 (s, C=), 670 (s, C=), 9, 4 (C ), 767 cm ; EIMS m/z 247 (M +, 32), 68 (4), 6 (00), 4 (32), 4 (); RMS Calcd for C 0 8 F 3 3 : ; Found: xo-2-{[3-(trifluoromethyl)phenyl]amino}ethyl formate (7h). Yield: 78%; yellow liquid; MR (CDCl 3, 200 Mz) δ 4.79 (s, 2, C 2 ), (m, 2, Ar), (m, 2, Ar), 7.98 (br,, ); 8.20 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.20, 6.79, 6.86, 2.63, 2.70, 23.8, 29.73, 0.73, - 4 -
5 .53,.82, 2.58, 2.83, 7.04, (C=), (C=); IR (KBr) 3425 (br, ), 728 (s, C=), 689 (s, C=), 6 (C ), 22, 698 cm ; EIMS m/z 247 (M +, 32), 6 (00), 60 (), 45 (5), 87 (22), 55 (37), 54 (5); RMS Calcd for C 0 8 F 3 3 : ; Found: xo-2-{[4-(trifluoromethyl)phenyl]amino}ethyl formate (7i). Yield: 9%; white solids; mp C; MR (CDCl 3, 500 Mz) δ 4.79 (s, 2, C 2 ), 7.59 (d, J = 8.5 z, 2, Ar), 7.67 (d, J = 8.5 z, 2, Ar), 8.20 (s,, =C ); C MR (CDCl 3, 25 Mz) δ 62.32, 9.77 (2 C + C), 2.43, 22.27, 22.63, 23.83, 23.07, 26.43, 26.46, 9.60, (C=), (C=); IR (KBr) 344 (br, ), 743 (s, C=), 678 (s, C=), 539, 65 (C ), 740 cm ; EIMS m/z 247 (M +, 34), 6 (00), 45 (2), 42 (2), (7), 87 (); RMS Calcd for C 0 8 F 3 3 : ; Found: xo-2-(p-tolylamino)ethyl formate (7j). Yield: 89%; white solids; mp 39 4 C; MR (CDCl 3, 200 Mz) δ 2.30 (s, 3, C 3 ), 4.75 (s, 2, C 2 ), 7. (d, J = 8.3 z, 2, Ar), 7.40 (d, J = 8.3 z, 2, Ar), 7.77 (br,, ), 8.8 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 20.88, 62.30, 9.87, (2 C), (2 C), 4.92, (C=), 64.4 (C=); IR (KBr) 3429 (br, ), 732 (s, C=), 678 (s, C=), 265, 65 (C ) cm ; EIMS m/z 93 (M +, 26), 65 (8), 4 (2), 07 (00), 06 (76), 9 (23), 77 (39), 65 (8); RMS Calcd for C 0 3 : ; Found: [(4-ydroxyphenyl)amino]-2-oxoethyl formate (7k). Yield: 87%; yellow liquid; MR (CDCl 3, 200 Mz) δ 4.77 (s, 2, C 2 ), 7.09 (d, J = 8.8 z, 2, Ar), 7.55 (d, J = 8.8 z, 2, Ar), 7.84 (br,, ), 8.9 (s,, =C ), 8.27 (s,, ); C MR (CDCl 3, 50 Mz) δ 62.29, 2.33 (2 C), 2.85 (2 C), 4.64, (C=), 59.2, (C=); IR (KBr) (br, + ), 2920, 728 (s, C=), 689 (s, C=), 92, 65 (C ) cm ; EIMS m/z 95 (M +, 40),
6 (00), 08 (33), 8 (); RMS Calcd for C : ; Found: [(4-Methoxyphenyl)amino]-2-oxoethyl formate (7l). Yield: 9%; brown solids; mp C; MR (CDCl 3, 200 Mz) δ 3.77 (s, 3, C 3 ), 4.75 (s, 2, C 2 ), 6.86 (d, J = 9.0 z, 2, Ar), 7.42 (d, J = 9.0 z, 2, Ar), 7.78 (br,, ), 8.8 (s,, =C ); C MR (CDCl 3, 25 Mz) δ 55.47, 62.33, 4.28 (2 C), 22. (2 C), 29.50, 57.00, (C=), (C=); IR (KBr) 3309 (br, ), 734 (s, C=), 668 (s, C=), 247, 49 (C ), 835 cm ; EIMS m/z 209 (M +, 64), 23 (49), 22 (35), (24), 08 (29), 9 (00), 77 (20); RMS Calcd for C 0 4 : ; Found: [(4-Cyanophenyl)amino]-2-oxoethyl formate (7m). Yield: 87%; white solids; mp C; MR (CDCl 3, 200Mz) δ 4.79 (s, 2, C 2 ), 7.62 (d, J = 9.0 z, 2, Ar), 7.70 (d, J = 9.0 z, 2, Ar), 8.04 (br,, ), 8.20 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.26, 08.5, 8.52, 9.93 (2 C), 3.40 (2 C), 40.55, (C=), (C=); IR (KBr) 3294 (br, ), 2225 (s, C) 732 (s, C=), 70 (s, C=), 5, 6 (C ) cm ; EIMS m/z 204 (M +, 28), 9 (2), 8 (00), 7 (4), 9 (6), 90 (7); RMS Calcd for C : ; Found: [(2,5-Dimethoxyphenyl)amino]-2-oxoethyl formate (7n). Yield: 76%; white liquid; MR (CDCl 3, 400 Mz) δ 3.72 (s, 3, C 3 ), 3.80 (s, 3, C 3 ), 4.73 (s, 2, C 2 ), 6.56 (dd, J =.6, 8.8 z,, Ar), 6.76 (d, J = 9.2 z, ), 8.02 (d, J = 2.8 z,, Ar), 8.7 (s,, =C ), 8.43 (br,, ); C MR (CDCl 3, 00 Mz) δ (C 3 ), 56. (C 3 ), 62.27, (C), (C), 0.68 (C), (C), 42.8 (C), (C), (C=), (C=); IR (KBr) 3745 (br, ), 325, 770 (s, C=), 666 (s, C=), 535, 29 (C ) cm ; EIMS m/z 239 (M +, 70), 224 (6), 65 (), 8 (00); RMS Calcd for C 5 : ; Found:
7 2-(aphthalen--ylamino)-2-oxoethyl formate (9a). Yield: 86%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.90 (s, 2, C 2 ), (m, 3, Ar), (m, 4, Ar), 8.27 (s,, =C ); C MR (CDCl 3, 50 Mz) δ 62.75, 20.32, 2.9, 25.69, 26.23, 26.6, 26.68, 28.87, 28.89, 0.87, 4.4, (C=), (C=); IR (KBr) 3248 (br, ), 726 (s, C=), 666 (s, C=), 27, 63 (C ), 767 cm ; EIMS m/z 229 (M +, 55), 79 (22), 43 (00), 5 (57), 93 (52), 77 (20); RMS Calcd for C 3 : ; Found: xo-2-(quinolin-8-ylamino)ethyl formate (9b). Yield: 87%; white solids; mp C; MR (CDCl 3, 200 Mz) δ 4.90 (s, 2, C 2 ), (m, 3, Ar), 8.4 (d, J = 8.3 z,, Ar), 8.32 (s,, =C ), (m, 2, Ar), 9.76 (br,, ); C MR (CDCl 3, 50 Mz) δ 62.6, 7.0, 2.78, 22.46, 27.29, 27.99, 6.4, 8.55, 48.56, 48.58, (C=), (C=); IR (KBr) 333 (), 734 (s, C=), 683 (s, C=), 53 (C ), 788 cm ; EIMS m/z 230 (M +, 0), 72 (7), 7 (00), 44 (46), 5 (23), 9 (2); RMS calcd for C : ; Found: xo-2-(Thiazolylamino)ethyl formate (9c). Yield: 7%; yellow liquid; MR (CDCl 3, 400 Mz) δ 4.90 (s, 2, C 2 ), 7.03 (d, J = 3.6 z, ), 7.47 (d, J = 3.6 z, ), 8.7 (s,, =C ); C MR (CDCl 3, 00 Mz) δ 6.50, 4.39 (C), 0.88 (C), 6.95 (C), (C=), (C=); IR (KBr) 3745 (br, ), 728 (s, C=), 678 (s, C=), 276, 6 (C ) cm ; EIMS m/z 86 (M +, 20), 27 (0), 00 (00), 9 (7), 73 (9), 58 (22), 55 (); RMS Calcd for C S: ; Found:
8 MR (CDCl3, 200 Mz) spectrum of compound 4 C MR (50 Mz, CDCl3) spectrum of compound 4-8 -
9 F MR (CDCl3, 200 Mz) spectrum of compound 7a F C MR (50 Mz, CDCl3) spectrum of compound 7a - 9 -
10 F MR (CDCl3, 200 Mz) spectrum of compound 7b F C MR (50 Mz, CDCl3) spectrum of compound 7b - 0 -
11 F MR (CDCl3, 200 Mz) spectrum of compound 7c F C MR (25 Mz, CDCl3) spectrum of compound 7c - -
12 Br MR (50 Mz, CDCl3) spectrum of compound 7d Br C MR (50 Mz, CDCl3) spectrum of compound 7d - 2 -
13 Br MR (CDCl3, 200 Mz) spectrum of compound 7e Br C MR (50 Mz, CDCl3) spectrum of compound 7e - -
14 Br MR (CDCl3, 200 Mz) spectrum of compound 7f Br C MR (50 Mz, CDCl3) spectrum of compound 7f - 4 -
15 CF 3 MR (CDCl3, 200 Mz) spectrum of compound 7g CF 3 C MR (50 Mz, CDCl3) spectrum of compound 7g - 5 -
16 F 3 C MR (CDCl3, 200 Mz) spectrum of compound 7h F 3 C C MR (50 Mz, CDCl3) spectrum of compound 7h - 6 -
17 F 3 C MR (CDCl3, 500 Mz) spectrum of compound 7i F 3 C C MR (25 Mz, CDCl3) spectrum of compound 7i - 7 -
18 Me MR (CDCl3, 200 Mz) spectrum of compound 7j Me C MR (50 Mz, CDCl3) spectrum of compound 7j - 8 -
19 MR (CDCl3, 200 Mz) spectrum of compound 7k C MR (50 Mz, CDCl3) spectrum of compound 7k - 9 -
20 Me MR (CDCl3, 200 Mz) spectrum of compound 7l Me C MR (50 Mz, CDCl3) spectrum of compound 7l
21 C MR (CDCl3, 200 Mz) spectrum of compound 7m C C MR (50 Mz, CDCl3) spectrum of compound 7m - 2 -
22 Me Me MR (CDCl3, 400 Mz) spectrum of compound 7n Me Me C MR (50 Mz, CDCl3) spectrum of compound 7n
23 MR (CDCl3, 200 Mz) spectrum of compound 9a C MR (50 Mz, CDCl3) spectrum of compound 9a
24 MR (CDCl3, 200 Mz) spectrum of compound 9b C MR (50 Mz, CDCl3) spectrum of compound 9b
25 S MR (CDCl3, 400 Mz) spectrum of compound 9c S C MR (00 Mz, CDCl3) spectrum of compound 9c
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