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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 27 Supporting information Phosphorous Acid Functionalized Polyacrylonitrile Fiber with Polarity Tunable Surface Micro-environment for ne-pot C-C and C- Bond Formation Reactions Gang Xu a, Lu Wang a, Mengmeng Li a, Minli Tao a and Wenqin Zhang* a,b a Department of Chemistry, School of Sciences, Tianjin University, Tianjin, 372, P. R. China. b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 372, P. R. China. * Corresponding author. zhangwenqin@tju.edu.cn
2 . Reagents and instruments Commercially available polyacrylonitrile fiber (PAF, the number average molecular weight of the spinning solution is 53 to 6, 93.% acrylonitrile, % methyl acrylate and.4-.5% sodium styrene sulfonate) was cut into lengths of about cm before use (from the Fushun Petrochemical Corporation of China). The aldehydes, 2-aminobenzamide, o- substituted aniline, ethanolamine, phosphorus oxychloride (PCl 3 ), n-butyl alcohol, benzylamine, 3-phenyl--propanol, and the other reagents etc. were analytical grade and used without further purification. The water was deionized. The mechanical properties of different fiber samples were tested with an electronic single fiber strength tester YG(B)A (Wenzhou Darong Textile Instrument Corporation, China) with clamping distance of mm and an elongation speed of 2 mm min - at room temperature. The FTIR spectra were obtained by an AVATAR36 FTIR spectrometer (Thermo icolet), all the samples were pulverized by cutting and made into pellets with KBr. The Elemental analysis (EA) were performed on a vario micro cube (Elementar). Scanning electron microscopy (SEM) (Hitachi, model S-48) was used to characterize the surface of the modified fibers. X-ray powder diffraction spectra (XRD) were recorded by a D/MAX- 25 X-ray diffractometer (Rigaku Corporation). Thermodynamic characteristics fiber were investigated using a STA49PC TGA/ DSC simultaneous thermalanalyzer (etzsch company, Germany). H MR (4 MHz) and 3 C MR ( MHz) spectra were recorded on BRUKER-AVACE III instruments using tetramethylsilane as the internal standard. itrogen adsorption and desorption isotherms were measured by a Auto-sorb-iQA32-4 surface area and pore size analyzer (Connor Instruments, USA). The samples were outgassed
3 at 2 o C overnight before measurements were made. HPLC analyses were performed on Waters Modol Synthesis of the hydroxyethylation fiber 2. Synthesis of the PA EA F Dried PAF (4. g), ethanolamine (4 ml) and water (6 ml) were placed in a threenecked flask. After the mixture was refluxed for 4 h, the fiber was filtered out and washed with water (6-7 C) until no ethanolamine was attached to the fiber surface by non-covalent bonds, and then dried at 6 C overnight to collect the hydroxyethylation fiber (PA EA F). The weight gain of PA EA F based on PAF was 5.%. 2.2 Synthesis of the Bn-PA EA F Dried PA EA F (3. g), Benzylamine ( ml) and H 2 (3 ml) were placed in a threenecked flask, and the mixture was heated at o C for.5 h. After cooling the mixture to room temperature, the fiber was filtered out and washed with water (6-7 C) and ethanol until no benzylamine was attached to the fiber surface by non-covalent bonds. Then the fiber was dried at 6 C overnight to get the Bn-PA EA F. The weight gain of Bn-PA EA F based on PA EA F was 8.3% Synthesis of the Bu-PA EA F Dried PA EA F (. g), n-butyl amine ( ml), a 2 C 3 (. g) and H 2 ( ml) were placed in a three-necked flask, and the mixture was heated at o C for.5 h. After cooling the mixture to room temperature, the fiber was filtered out. The fiber was washed with water
4 (6-7 C) and ethanol until no n-butyl amine was attached to the fiber surface by noncovalent bonds, and then dried at 6 C overnight to get the Bu-PA EA F. The weight gain of Bu-PA EA F based on PA EA F was 6.6%. 3. Acid exchange capacity Dried fibers (. g) were immersed into 5 ml of. mol L - ah for 4 h. The neutralized fibers were then filtered and the concentration of the remaining solution were determined by titration with. mol L - HCl. The total acid contents were calculated based on the consumption of the base. 4. The WCA photographs of the fibers (a) PAF 64.2 o (b) PAEAF (c) PAEAPF 26.4 o 32.2 o (d) Bn-PAEAPF (e) PAEAPF-Bn 78.3 o 79.3 o Fig. S. The WCA photographs of (a) PAF, (b) PA EA F, (c) PA EAP F, (d) Bn-PA EAP F and (e) PA EAP F-Bn.
5 5. The FTIR spectra of PA EAP F, PA EAP F-Bn, Bu-PA EAP F, PA EAP F-Bu Fig S2. The FTIR spectra of (a) PA EAP F, (b) PA EAP F-Bn, (c) Bu-PA EAP F, (d) PA EAP F- Bu. 6. Specific surface area analysis Table S. Specific surface area analysis Entry Fiber S BET (m 2 g - ) V Tot (cm 3 g - ) Average pore diameter (nm) PAF PA EA F PA EAP F Bn-PA EAP F Bu-PA EAP F PA EAP F-Bn PA EAP F-Bu
6 7. The SEM images of PA EAP F, Bu-PA EAP F, BPA EAP F-Bn, PA EAP F-Bu a b c d Fig. S3. The SEM images of (a) PA EAP F, (b) Bu-PA EAP F, (c) BPA EAP F-Bn, (d) PA EAP F-Bu. 8. Thermal stability of fibers Fig. S4. TGA spectra of (a) PAF, (b) PA EA F, (c) PA EAP F, (d) Bn-PA EAP F, (e) Bu- PA EAP F, (f) PA EAP F-Bn and (g) PA EAP F-Bu.
7 9. Catalytic test 9.. General experimental procedure of the fiber catalyzed cyclocondensation reactions of 2-aminobenzamides with β-ketoesters for the synthesis of -heterocycle derivatives: The 2-aminobenzamides ( mmol), β-ketoesters (.5 mmol), fiber catalyst (5 mol%) and water (5 ml) were added in a screw-capped pressure bottle equipped with a magnetic stirrer. The reaction mixture was stirred at o C for 5 h and monitored by TLC or HPLC. After completion of the reaction, the system was cooled to room temperature. The fiber catalyst was taken out with tweezers and washed with ethyl acetate (5 ml 3) and was directly used for next run. The ethyl acetate solution was mixed with the reaction mixture. After extraction and washing with water, the organic phase was dried using a 2 S 4. After evaporation of the solvent, the residue was purified by a silica gel column (eluent: ethyl acetate/petroleum ether=/2-/5) to get the corresponding pure product General experimental procedure of the fiber catalyzed Knoevenagel condensation of aromatic aldehydes with active methylene compounds: The aldehyde ( mmol), malononitrile (. mmol) and Bn-PA EAP F (5 mol%) were added to ml of H 2 in a single-necked flask and the mixture was stirred at room temperature for 2 h. The progress of the reaction was monitored by TLC or HPLC. After the process was completed, the fiber catalyst was taken out with tweezers and washed with ethyl acetate (5 ml 3) and then was directly used for next run. The ethyl acetate solution was mixed with the reaction mixture. After extraction and washing with water, the organic phase was dried using a 2 S 4. After evaporation of the solvent, the residue was purified by a silica gel column (eluent: ethyl acetate/petroleum ether=/5-/) to get the corresponding pure product.
8 9.3. General experimental procedure of the fiber catalyzed Biginelli reactions using Bn- PA EAP F A mixture of aldehyde ( mmol), methylene compound (.2 mmol), urea (.2 mmol), ethanol (5 ml) and Bn-PA EAP F (5 mol%) were added in a screw-capped pressure bottle equipped with a magnetic stirrer. The reaction mixture was stirred at 8 o C for 2 h and monitored by TLC or HPLC. After completion of the reaction, the system was cooled to room temperature. The fiber catalyst was taken out with tweezers and washed with ethanol (5 ml 3) and was directly used for next run. The ethanol solution was mixed with the reaction mixture, and the solvent of the mixture was evaporated under reduced pressure. The residue was washed with water (5 ml) and extracted with ethyl acetate ( ml), the organic phase was dried using a 2 S 4. After evaporation of the solvent, the product is almost pure. Further purification of the product was treated simply through a silica gel column (eluent: ethyl acetate/petroleum ether=/2-/) The effect of the solvent polarity on the reaction Table S2. The effect of the solvent polarity on the reaction a Entry Catalyst dosage Solvent Yield (%) b PA EAP F 5 mol% EtH:H 2 (:) 59 2 PA EAP F 5 mol% EtH:H 2 (9:) 5 3 PA EAP F 5 mol% EtH:H 2 (7:3) 36 4 PA EAP F 5 mol% EtH:H 2 (5:5) 3 5 PA EAP F 5 mol% EtH:H 2 (3:7) 3 6 PA EAP F 5 mol% EtH:H 2 (:9) 29 7 PA EAP F 5 mol% EtH:H 2 (:) 44
9 a Reaction conditions: 2-aminobenzamide ( mmol), ethyl acetoacetate (.5 mmol), solvent (5 ml) and catalyst dosage based on acid content, the solvents with different polarities were obtained by adjusting the ratio of water to ethanol. b The yields were obtained by HPLC using m-binitrobezene as an internal standard Comparison of catalytic activity of fiber catalysts in ethanol Table S3. Comparison of catalytic activity of fiber catalysts in ethanol a Entry Catalyst Temp ( C) Time (h) Yield (%) b PA EAP F Bn-PA EAP F Bu-PA EAP F PA EAP F-Bn PA EAP F-Bu PA EAP F PA EAP F a Reaction conditions: 2-aminobenzamide ( mmol), ethyl acetoacetate (.5 mmol), solvent (5 ml) and catalyst dosage based on acid content. b The yields were obtained by HPLC using m- binitrobezene as an internal standard Comparison of the Knoevenagel condensation using different supported catalysts Table S4. Comparison of the Knoevenagel condensation using different supported catalysts. Entry Catalyst Catalyst solvent Temperature Yield (%) Ref. dosage /Ttime Pd/Cz-MF mg toluene 8 o C/5 h 99 (Conversion) [] 2 Ui-66 R 2 mol% toluene Rt/2 h 97 [2] 3 Fe34@Si mg THF 75 o C/5 min (Conversion) [3] 4 Microporous carbon nitride mg C 9 o C /4 h 87 [4] 5 polystyrene-supported mol% CH 3 H Rt/5 min 99 [5] DABC 6 Fe 3 4 cysteamine 5 mg Ethanol water 5 o C/2 min 93 [6] hydrochloride (/) 7 C/Co@DMA 2 mol % H 2 Rt/ h 97 [7] 8 Bn-PA EAP F 5 mol% (33 mg) H 2 Rt/2 h 94 This study
10 9.7. The reaction of p-methoxybenzaldehyde with urea and ethyl benzoylacetate Scheme S. The reaction of p-methoxybenzaldehyde with urea and ethyl benzoylacetate Comparison of the Biginelli reaction using different heterogeneous catalysts Table S5. Comparison of the Biginelli reaction using different heterogeneous catalyst. Entry Catalyst Catalyst dosage Yield Ref. Yb(III)-resin 3 mg 72 [8] 2 Fe 3 5 mg 82 [9] 3 PS-PEG-S 3 H 3 mg 79 [] 4 PPF-S 3 H 75 mg 89 [] 5 Fe 3 2 -imid-pma 3 mg 9 [2] 6 PSBIL 5 mg 92 [3] 7 Cobalt-basedmetal coordination polymers 2 mol % 94 [4] 8 ano-fe 3 sulfuric acid 6 mg 89 [5] 9 PPA-Si 2 6 mg 94 [6] Bn-PA EAP F 5 mol% (33 mg) 94 This study. MR data of products a-v, 2a-2p and 3a-3m. Methylquinazolin-4(3H)-one (a) H MR (4 MHz, CDCl 3 ) δ 2.36 (s, H), 8.29 (d, J = 7.9 Hz, H), 7.78 (t, J = 7.6 Hz, H), 7.69 (d, J = 8. Hz, H), 7.48 (t, J = Hz, H), 2.62 (s, 3H); 3 C MR ( MHz, DMS) δ 62.6, 54.93, 49., 34.77, 26.79, 26.37, 26.7,, Ethylquinazolin-4(3H)-one (b) H MR (4 MHz, DMS) δ 2.8 (s, H), 8.9 (s, H), 7.77 (s, H), 7.6 (s, H), 7.46 (s, H), 2.63 (s, 2H),.25 (s, 3H); 3 C MR ( MHz, DMS) δ 62.27, 58.79, 49.42, 34.72, 27.27, 26.38, 2, 2.29, 28.3, Propylquinazolin-4(3H)-one (c) H MR (4 MHz, CDCl 3 ) δ 2.3 (s, H), 8.23 (d, J = 7.9 Hz, H), 7.7 (t, J = Hz, H), 7.64 (d, J = 8. Hz, H), 7.4 (t, J = 7.4 Hz, H), 2.73 (t, J = 7.6 Hz, 2H), (m, 2H),.2 (t, J = 7.3 Hz, 3H); 3 C MR ( MHz, CDCl 3 ) δ 63.38, 55.76, 48.49, 33.76, 26.2, 25.3, 25.2, 9.47, 36.74, 9.99, 2.73.
11 2-Cyclopropylquinazolin-4(3H)-one (d) H MR (4 MHz, DMS) δ 2.45 (s, H), (d, J = 7.9 Hz, H), 7.72 (t, J = 7.6 Hz, H), 7.48 (d, J = 8.2 Hz, H), 7.39 (t, J = Hz, H),.96 (m, H),.9 (m, 2H),.3 (m, 2H); 3 C MR ( MHz, DMS) δ 62.8, 59.48, 49.58, 26.94, 26.2, 25.77, 2.9, 3.89, Chloromethylquinazolin-4(3H)-one (e) H MR (4 MHz, CDCl 3 ) δ (s, H), 8.3 (d, J = 7.9 Hz, H), 7.8 (m, J = 7.6 Hz, H), 7.68 (d, J = 8. Hz, H), 4 (m, J = Hz, H), 4.56 (s, 2H); 3 C MR ( MHz, DMS) δ 62.6, 52.7, 49, 35., 27.76, 27.64, 26.36, 2.73, Methoxymethylquinazolin-4(3H)-one (f) H MR (4 MHz, CDCl 3 ) δ 9.67 (s, H), 8.22 (d, J = 7.9 Hz, H), 7.7 (t, J = 7.6 Hz, H), 9 (d, J = 8.2 Hz, H), 7.42 (t, J = Hz, H), 4.43 (s, 2H), 3.48 (s, 3H); 3 C MR ( MHz, CDCl 3 ) δ 6.62, 52.68, 48.62, 34.82, 27.8, 26.86, 26.66, 2.62, 7.3, ,3-Dimethylquinazolin-4(3H)-one (g) H MR (4 MHz, CDCl 3 ) δ 8.26 (d, J = 7.9 Hz, H), 7.72 (t, J = 7.6 Hz, H), 7.6 (d, J = 8. Hz, H), 7.44 (t, J = Hz, H), 3.64 (s, 3H), 2.63 (s, 3H); 3 C MR ( MHz, CDCl 3 ) δ 62.32, 54.44, 47.27, 34.9, 26.8, 26.62, 26.4, 2.24,, Chloro-2,3-Dimethylquinazolin-4(3H)-one (h) H MR (4 MHz, DMS) δ 2.39 (s, H), 7.99 (s, H), 7.78 (d, J = 8.6 Hz, H), 8 (d, J = 8.6 Hz, H), 2.35 (s, 3H); 3 C MR ( MHz, DMS) δ 6.4, 55.32, 4, 34.83, 2, 29.33, 25.2, 22.35, methoxy-2-methylquinazolin-4(3H)-one (i) H MR (4 MHz, DMS) δ 2.6 (s, H), 2 (d, J = 8.8 Hz, H), 7.46 (s, H), 7.37 (d, J = 8.8 Hz, H), 3.86 (s, 3H), 2.32 (s, 3H); 3 C MR ( MHz, DMS) δ 62., 58, 52.25, 43.93, 28.7, 24.2, 2.79, 6.2, 55.98, Phenylquinazolin-4(3H)-one (j) H MR (4 MHz, CDCl 3 ) δ.3 (s, H), 8.27 (d, J = 7.9 Hz, H), 8.7 (d, J = Hz, 2H), 7.77 (t, J = 8.7 Hz, 2H), 3 (s, 3H), 7.45 (t, J = 7.2 Hz, H); 3 C MR ( MHz, CDCl 3 ) δ 63.6, 5.7, 49.5, 34.93, 32.84, 3.7, 29.3, 2, 27.3, 26.86, 26.42, (4-Methoxyphenyl)quinazolin-4(3H)-one (k) H MR (4 MHz, DMS) δ 2.44 (s, H), 8.2 (d, J = 8. Hz, 2H), 8.4 (d, J = 7.7 Hz, H), 7.8 (t, J = 7.3 Hz, H), 7.7 (d, J = 8. Hz, H), 7.49 (t, J = 7.2 Hz, H), 7. (d, J = 8. Hz, 2H), 3.86 (s, 3H); 3 C MR ( MHz, DMS) δ 62.78, 62.33, 52.33, 49.4, 35.2, 29.93, 27.76, 26.6, 26.3, 25.26, 2.6, 4.47, Chloro-2-(4-methoxyphenyl)quinazolin-4(3H)-one (l) H MR (4 MHz, DMS) δ 9 (s, H), 8.9 (d, J = 8. Hz, 2H), 8.6 (s, H), 7.83 (d, J = Hz, H), 7.72 (d, J = Hz, H), 7.9 (d, J = 8. Hz, 2H), 3.86 (s, 3H); 3 C MR ( MHz, DMS) δ 62.3, 6.95, 52.99, 48.6, 34.94, 5, 29.99, 25.25, 24.92, 22.2, 4.4, methoxy-2-(4-methoxyphenyl)quinazolin-4(3H)-one (m) H MR (4 MHz, DMS) δ 2.4 (s, H), 8.6 (d, J = 8.3 Hz, 2H), 7.66 (d, J = 8.8 Hz, H), 3 (s, H), 7.43 (d, J = 8.7 Hz, H), 7.8 (d, J = 8.3 Hz, 2H), 3.89 (s, 3H), 3.85 (s, 3H); 3 C MR ( MHz, DMS) δ 68, 6, 57.9, 5.2, 43.89, 29.6, 29.47, 25.4, 24.57, 2.9, 4.44,
12 6.29, 56.8, (4-Fluorophenyl)quinazolin-4(3H)-one (n) H MR (4 MHz, DMS) δ 2.6 (s, H), (m, 2H), 8.6 (d, J = 7.8 Hz, H), 7.85 (t, J = Hz, H), 7.74 (d, J = 8. Hz, H), 3 (t, J = 7.4 Hz, H), 7.4 (t, J = Hz, 2H). 3 C MR ( MHz, DMS) δ 65.67, 63.23, 62.69, 5.82, 49.2, 35.2, 3.89, 3.8, 29.69, 27.93, 27.9, 26.33, 2.35, 6.22, (4-itrophenyl)quinazolin-4(3H)-one (o) H MR (4 MHz, DMS) δ 2.86 (s, H), (m, 4H), 8.9 (d, J = Hz, H), 7.89 (t, J = Hz, H), 7.8 (d, J = 8. Hz, H), 9 (t, J = 7.3 Hz, H). Ethyl-2-(2-(4-nitrophenyl)-4-oxo-,2,3,4-tetrahydroquinazolin-2-yl)acetate (o ) H MR (4 MHz, DMS) δ 8.83 (s, H), 8.2 (d, J = 8.3 Hz, 2H), 7.82 (d, J = 8.3 Hz, 2H), 7.75 (s, H), (d, J = 7.7 Hz, H), 7.26 (t, J = 7.6 Hz, H), 6.93 (d, J = 8. Hz, H), 6.65 (t, J = 7.3 Hz, H), 4.2 (q, J = 6.8 Hz, 2H), 3.4 (dd, J = 35.3, 4.9 Hz, 2H),.9 (t, J = 7. Hz, 3H). 2-Methyl-H-benzoimidazole (p) H MR (4 MHz, CDCl 3 ) δ 6 (dd, J = Hz, 2H), 7.24 (dd, J = 9., 6. Hz, 2H), 2.66 (s, 3H); 3 C MR ( MHz, CDCl 3 ) δ 5.3, 38.38, 22.3, 4.37, (Methoxymethyl)-H-benzoimidazole (q) H MR (4 MHz, CDCl 3 ) δ.2 (s, H), 7.6 (s, 2H), (m, 2H), 4.78 (s, 2H), 3.49 (s, 3H); 3 C MR ( MHz, CDCl 3 ) δ 5.57, 22.62, 6.69, 68.42, cyclopropyl-H-benzo[d]imidazole (r) H MR (4 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), 2.3 (m, H),.29.2 (m, 2H),.9 (m, 2H). 2-chloromethyl-H-benzimidazole (s) H MR (4 MHz, CDCl 3 ) δ 4 (s, 2H), (m, 2H), 4.8 (s, 2H). 2-(4-Methoxyphenyl)-H-benzo[d]imidazole (t) H MR (4 MHz, DMS) δ 2.75 (s, H), 8.3 (d, J = 5. Hz, 2H), 7 (d, J = 42.9 Hz, 2H), (m, 4H), 3.87 (s, Hz, 3H). 2-(4-itrophenyl)-H-benzo[d]imidazole (u) H MR (4 MHz, DMS) δ 3.3 (s, H), 8.42 (s, 4H), (m, 2H), 7.27 (s, 2H). 2-(pyridin-4-yl)-H-benzo[d]imidazole (v) H MR (4 MHz, DMS) δ 3.27 (s, H), 8.77 (d, J = 4.3 Hz, 2H), 8. (d, J = 4.3 Hz, 2H), 7.66 (s, 2H), 7.28 (s, 2H). 2-(Phenylmethylene)malononitrile (2a) H MR (4 MHz, CDCl 3 ) δ 7.85 (d, J = 7.8 Hz, 2H), 7.72 (s, H), 7 (t, J = 7.4 Hz, H), 7.48 (t, J = 7.6 Hz, 2H). 2-(2-nitrobenzylidene)malononitrile (2b) H MR (4 MHz, CDCl 3 ) δ 8.46 (s, H), 8.37 (d, J = 8.6 Hz, H), (m, 3H). 2-(3-nitrobenzylidene)malononitrile (2c) H MR (4 MHz, CDCl 3 ) δ 8.67 (s, H), 8.49 (d, J = 8.2 Hz, H), 8.34 (d, J = 7.9 Hz, H), 7.9 (s, H), 7.8 (t, J = 8. Hz, H). 2-(4-nitrobenzylidene)malononitrile (2d) H MR (4 MHz, CDCl 3 ) δ 8.4 (d, J = Hz, 2H), 8.9 (d, J = Hz, 2H), 7.9 (s, H).
13 2-(3-Methoxyphenylmethylene)malononitrile (2e) H MR (4 MHz, CDCl 3 ) δ 7.76 (s, H), (s, H), (m, 2H), 7.8 (d, J = 7.3 Hz, H), 3.87 (s, 3H). 2-(4-Methoxyphenylmethylene)malononitrile (2f) H MR (4 MHz, CDCl 3 ) δ 7.92 (d, J = 8.7 Hz, 2H), 7.66 (s, H), 7.2 (d, J = 8.7 Hz, 2H), 3.92 (s, 3H). 4-(-dimethylamino benzylidene) malononitrile (2g) H MR (4 MHz, CDCl 3 ) δ 7.75 (d, J = 8.7 Hz, 2H), 7.4 (s, H), 6.62 (d, J = 8.7 Hz, 2H), 3.8 (s, 6H). 2-(4-hydroxyphenylmethylene)malononitrile (2h) H MR (4 MHz, DMS) δ 8.38 (s, H), 7.96 (d, J = 8.4 Hz, 2H), 7.4 (d, J = 8.4 Hz, 2H); 3 C MR ( MHz, DMS) δ (m), (m), (m), (m), (m), (m), (m), (m). 4-chlorobenzylidenemalonodinitrile (2i) H MR (4 MHz, CDCl 3 ) δ 7.87 (d, J = 8.3 Hz, 2H), 7.74 (s, H), 3 (d, J = 8.3 Hz, 2H). 2-(3-bromobenzylidene)malononitrile (2j) H MR (4 MHz, CDCl 3 ) δ 7.9 (s, H), 7.84 (d, J = 7.9 Hz, H), (m, 2H), 7.37 (t, J = 8. Hz, H). 2-(2-trifluoromethylbenzylidene)malononitrile (2k) H MR (4 MHz, CDCl 3 ) δ 8.23 (s, H), 8.8 (d, J = 7.3 Hz, H), 7.85 (d, J = 7.3 Hz, H), 7.75 (p, J = 7.4 Hz, 2H). [(2-chloro-3-quinolyl)methylidene]methane-,-dicarbonitrile (2l) H MR (4 MHz, CDCl 3 ) δ 9.2 (s, H), 8.37 (s, H), 8.7 (d, J = Hz, H), 8. (d, J = 8.2 Hz, H), 7.94 (t, J = 7.7 Hz, H), 7.7 (t, J = 7.6 Hz, H). 2-(2-Furylmethylene)malonitrile (2m) H MR (4 MHz, CDCl 3 ) δ 7.9 (d, J = 4.2 Hz, 2H), 7.8 (d, J = 3.7 Hz, H), (m, H),.59 (s, H). Cinnamalmalononitrile (2n) H MR (4 MHz, CDCl 3 ) δ (m, 3H), (m, 3H), 7.28 (d, J =.7 Hz, 2H),.59 (d, J = 3.2 Hz, H). Ethyl benzylidenecyanoacetate (2o) H MR (4 MHz, CDCl 3 ) δ 8.27 (s, H), 8. (d, J = 7.7 Hz, 2H), 4 (dq, J = 4.8, 7.4 Hz, 3H), 4.4 (q, J = 7. Hz, 2H),.4 (t, J = 7. Hz, 3H). 2-cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester (2p) H MR (4 MHz, CDCl 3 ) δ 8.36 (d, J = 8.4 Hz, 2H), 8.3 (s, H), 8.4 (d, J = Hz, 2H), 4.43 (q, J = 7. Hz, 2H),.43 (t, J = 7. Hz, 3H). 5-Ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(H)-one (3a) H MR (4 MHz, DMS) δ 9.25 (s, H), 7.79 (s, H), 7.38 (t, J = 7.3 Hz, 2H), 7.29 (d, J = 7. Hz, 3H), 5.2 (s, H), 4.4 (q, J = 6.9 Hz, 2H), 2.3 (s, 3H),.5 (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.8, 52.6, 48.83, 45.34, 28.86, 27.73, 26.72, 99.73, 59.65, 54.43, 8.25, Ethoxycarbonyl-4-(4-methylphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3b) H MR (4 MHz, DMS) δ 9.4 (s, H), 7.68 (s, H), 7.2 (s, 4H), 5. (s, H), 3.99 (q, J = 6.9 Hz, 2H), 2.26 (d, J = 8.2 Hz, 6H),. (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.83, 52.66, 48.6, 42.43, 36.83, 29.35, 26.62, 99.9, 59.62, 54., 2., 8.22, Ethoxycarbonyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3c) H
14 MR (4 MHz, DMS) δ 9.4 (s, H), 7.66 (s, H), (d, J = 8.3 Hz, 2H), 6.88 (d, J = 8.4 Hz, 2H), 5. (s, H), 3.99 (dd, J = 4., 6.9 Hz, 2H), 3.73 (s, 3H), 2.25 (s, 3H),. (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.85, 58.92, 52.64, 48.46, 33, 27.87, 4.7,.7, 59.6, 55.52, 53.82, 8.22, Ethoxycarbonyl-4-(3-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3d) H MR (4 MHz, DMS) δ 9. (s, H), 7.24 (d, J = 4.7 Hz, 2H), 7.6 (d, J = 7.3 Hz, H), 6.99 (d, J = 8. Hz, H), 6.88 (t, J = 7. Hz, H), 5.5 (s, H), 3.93 (t, J = 6.9 Hz, 2H), 3.8 (s, 3H), 2.29 (s, 3H),.3 (t, J = 6.4 Hz, 3H); 3 C MR ( MHz, DMS) δ 65.82, 57., 52.67, 49.29, 32., 29.3, 25, 2.62,.6, 98.9, 59.44, 55.84, 49.38, 8.7, Ethoxycarbonyl-4-(2-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3e) H MR (4 MHz, DMS) δ 9.8 (s, H), 7.72 (s, H), 7.25 (t, J = 7.8 Hz, H), (m, 3H), 5.3 (s, H), 4. (q, J = 6.9 Hz, 2H), 3.73 (s, 3H), 2.25 (s, 3H),.2 (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.82, 59.69, 52.69, 48.89, 46.8, 3.2, 8.7, 2.87, 2.6, 99.64, 59.68, 55.43, 54.22, 8.23, Ethoxycarbonyl-4-(3-trifluoromethylphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3f) H MR (4 MHz, DMS) δ 9.3 (s, H), 7.84 (s, H), 7.68 (m, 4H), 5.26 (s, H), (m, 2H), 2.27 (s, 3H),.8 (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.59, 52.33, 49.59, 46.72, 3.78, 3.26, 29.5, 25.99, 24.55, 23.42, 99.3, 59.76, 54.23, 8.27, Ethoxycarbonyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidin-2(H)-one (3g) H MR (4 MHz, DMS) δ 9.36 (s, H), 8.22 (d, J = 8.3 Hz, 2H), 7.9 (s, H), (d, J = 8.3 Hz, 2H), 5.28 (s, H), 3.99 (q, J = 6.9 Hz, 2H), 2.27 (s, 3H),. (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.53, 52.47, 52.24, 49.86, 47.8, 28.3, 24.29, 98.65, 59.86, 54.6, 8.34, (4-Chlorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(H)-one (3h) H MR (4 MHz, DMS) δ 9.23 (s, H), 7.76 (s, H), 7.4 (d, J = 8. Hz, 2H), 7.26 (d, J = 8. Hz, 2H), 5.5 (s, H), 3.99 (q, J = 6.8 Hz, 2H), 2.26 (s, 3H),. (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.68, 52.42, 49.8, 44.27, 32.26, 28.85, 28.66, 99.33, 59.72, 53.9, 8.27, (3-Bromophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(H)-one (3i) H MR (4 MHz, DMS) δ 9.27 (s, H), 7.79 (s, H), 7.46 (d, J = 7.7 Hz, H), 7.4 (s, H), 7.32 (t, J = 7.7 Hz, H), 7.25 (d, J = 7.6 Hz, H), 5.5 (s, H), (m, 2H), 2.26 (s, 3H),. (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.63, 52.39, 49.43, 47.96, 3.28, 3.62, 29.65, 25.74, 22., 99.8, 59.78, 54.7, 8.29, Ethoxycarbonyl-6-methyl-4-(2-thienyl)-3,4-dihydropyrimidin-2(H)-one (3j) H MR (4 MHz, DMS) δ 9.3 (s, H), 7.9 (s, H), 7.36 (d, J = 4.6 Hz, H), (m, 2H), 5.43 (s, H), 4.7 (q, J = 7. Hz, 2H), 2.23 (s, 3H),.8 (t, J = 7. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.5, 52.73, 49.27, 49., 27.2, 25.8, 23.98,.28, 59.82, 49.84,, (ethoxycarbonyl)-6-methyl-4-styryl-3,4-dihydropyrimidin-2(H)-one (3k) H MR (4 MHz, DMS) δ 9.6 (s, H), 6 (s, H), 7.4 (d, J = 6.7 Hz, 2H), (m, 2H), 7.25 (m,
15 m H), 6.37 (d, J = 5.7 Hz, H), 6.2 (dd, J = 5.4, 4.7 Hz, H), 4.73 (s, H), 4.9 (dd, J =.2, Hz, 2H), 2.2 (s, 3H),.2 (t, J = 6. Hz, 3H); 3 C MR ( MHz, DMS) δ 65.68, 53.7, 49.2, 36.7, 3.44, 29.4, 28, 28.6, 26.8, 98.26, 59.69, 52.36, 8.9, Acetyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3l) H MR (4 MHz, DMS) δ 9.24 (s, H), 7.85 (s, H), 7.24 (d, J = 8. Hz, 2H), 6.97 (d, J = 8. Hz, 2H), 5.29 (s, H), 3.8 (s, 3H), 2.36 (s, 3H), 2.6 (s, 3H); 3 C MR ( MHz, DMS) δ 94.85, 58.99, 59, 48.27, 36.84, 28.2, 4.32,.8, 55.52, 53.8, 3.63, 9.3. Benzyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-,2,3,4-tetrahydropyrimidine-5-carboxylate (3m) H MR (4 MHz, DMS) δ 9.24 (s, H), 7.7 (s, H), 7.29 (s, 3H), 7.4 (dd, J = 3., 6.8 Hz, 4H), 6.87 (t, J = 8. Hz, 2H), 5.4 (s, H), 5.4 (q, J = 2.8 Hz, 2H), 3.73 (s, 3H), 2.27 (s, 3H); 3 C MR ( MHz, DMS) δ 65.58, 58.99, 52.49, 49.4, 37.35, 37.3, 28.74, 28.7, 27.98, 27.96, 4.2, 99.52, 65.22, 55.55, 53.8, Ethyl 2-benzoyl-3-(4-methoxyphenyl)acrylate (3n) H MR (4 MHz, DMS) δ 7.9 (d, J = 8.9 Hz, 3H), 7.67 (t, J = 6.9 Hz, H), 4 (t, J = Hz, 2H), 7.35 (d, J = 8. Hz, 2H), 6.89 (d, J = 8. Hz, 2H), 4.6 (q, J = 6.8 Hz, 2H), 3.72 (s, 3H),. (dd, J = 6., 9.3 Hz, 3H).
16 . MR spectra of products a-v, 2a-2p and 3a-3m. Methylquinazolin-4(3H)-one (a) xg H MR of a XG C MR of a
17 2-Ethylquinazolin-4(3H)-one (b). XG H MR of b XG C MR of b
18 2-Propylquinazolin-4(3H)-one (c) xg H MR of c 3 C MR of c
19 2-Cyclopropylquinazolin-4(3H)-one (d) XG XG C MR of d H MR of d
20 2-Chloromethylquinazolin-4(3H)-one (e) xg Cl 7 6 H MR of e xg Cl 3 C MR of e
21 2-Methoxymethylquinazolin-4(3H)-one (f) xg CH 3 H MR of f XG CH C MR of f
22 2,3-Dimethylquinazolin-4(3H)-one (g) H MR of g XG C MR of g
23 6-Chloro-2,3-Dimethylquinazolin-4(3H)-one (h) xg xg Cl Cl 3 C MR of h H MR of h
24 6-methoxy-2-methylquinazolin-4(3H)-one (i) H MR of i XG C MR of i
25 2-Phenylquinazolin-4(3H)-one (j) xg H MR of j xg C MR of j
26 2-(4-Methoxyphenyl)quinazolin-4(3H)-one (k) xg CH 3 35 H MR of k XG C MR of k CH
27 6-Chloro-2-(4-methoxyphenyl)quinazolin-4(3H)-one (l) XG Cl H MR of l CH Cl C MR of l CH
28 6-methoxy-2-(4-methoxyphenyl)quinazolin-4(3H)-one (m) 2742-XG H MR of m CH XG C MR of m CH
29 2-(4-Fluorophenyl)quinazolin-4(3H)-one (n) xg XG XG F F 3 C MR of n H MR of n
30 2-(4-itrophenyl)quinazolin-4(3H)-one (o) Ethyl-2-(2-(4-nitrophenyl)-4-oxo-,2,3,4-tetrahydroquinazolin-2-yl)acetate (o ) XG H MR of o H MR of o
31 2-Methyl-H-benzoimidazole (p) XG H MR of p XG C C MR of p
32 2-(Methoxymethyl)-H-benzoimidazole (q) XG H MR of q XG c C MR of q
33 2-cyclopropyl-H-benzo[d]imidazole (r) XG H MR of r chloromethyl-H-benzimidazole (s) XG Cl H MR of s
34 2-(4-Methoxyphenyl)-H-benzo[d]imidazole (t) XG H MR of t (4-itrophenyl)-H-benzo[d]imidazole (u) XG H MR of u
35 2-(pyridin-4-yl)-H-benzo[d]imidazole (v) XG H MR of v (Phenylmethylene)malononitrile (2a) C H MR of 2a C
36 2-(2-nitrobenzylidene)malononitrile (2b) C C H MR of 2b (3-nitrobenzylidene)malononitrile (2c) C C H MR of 2c
37 2-(4-nitrobenzylidene)malononitrile (2d) C C 2 H MR of 2d (3-Methoxyphenylmethylene)malononitrile (2e) C C CH 3 H MR of 2e
38 2-(4-Methoxyphenylmethylene)malononitrile (2f) C C H MR of 2f (-dimethylamino benzylidene) malononitrile (2g) C C H MR of 2g
39 2-(4-hydroxyphenylmethylene)malononitrile (2h) C C H H MR of 2h H C C C MR of 2h
40 4-chlorobenzylidenemalonodinitrile (2i) Cl H MR of 2i C C (3-bromobenzylidene)malononitrile (2j) C 65 Br C H MR of 2j
41 2-(2-trifluoromethylbenzylidene)malononitrile (2k) CF 3 C C H MR of 2k [(2-chloro-3-quinolyl)methylidene]methane-,-dicarbonitrile (2l) C Cl C H MR of 2l
42 2-(2-Furylmethylene)malonitrile (2m) 3 S C C H MR of 2m Cinnamalmalononitrile (2n) C 8 C 7 H MR of 2n
43 Ethyl benzylidenecyanoacetate (2o) C H MR of 2o CEt cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester (2p) CEt C 8 H MR of 2p
44 5-Ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(H)-one (3a) 27523XG H MR of 3a xg C MR of 3a
45 5-Ethoxycarbonyl-4-(4-methylphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3b) xg CH H MR of 3b XG-4 CH C MR of 3b
46 5-Ethoxycarbonyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3c) xg CH H MR of 3c XG-3 CH C MR of 3c
47 5-Ethoxycarbonyl-4-(3-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3d) xg CH H MR of 3d XG CH C MR of 3d
48 5-Ethoxycarbonyl-4-(2-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3e) xg CH H MR of 3e XG CH C MR of 3e
49 5-Ethoxycarbonyl-4-(3-trifluoromethylphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3f) 2758-xg F F 7 65 F 6 H MR of 3f xg F F 3 F 2 3 C MR of 3f
50 5-Ethoxycarbonyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidin-2(H)-one (3g) 27523XG H MR of 3g XG C MR of 3g
51 4-(4-Chlorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(H)-one (3h) xg Cl H MR of 3h XG-2 Cl C MR of 3h
52 4-(3-Bromophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(H)-one (3i) 2758-xg Br H MR of 3i 2758-xg xg- Br C MR of 3i
53 5-Ethoxycarbonyl-6-methyl-4-(2-thienyl)-3,4-dihydropyrimidin-2(H)-one (3j) xg S H MR of 3j XG-6 S C MR of 3j
54 5-(ethoxycarbonyl)-6-methyl-4-styryl-3,4-dihydropyrimidin-2(H)-one (3k) XG H MR of 3k xg C MR of 3k
55 5-Acetyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(H)-one (3l) XG CH H MR of 3l xg CH C MR of 3l
56 Benzyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-,2,3,4-tetrahydropyrimidine-5-carboxylate (3m) 27525XG CH H MR of 3m xg CH C MR of 3m
57 Ethyl 2-benzoyl-3-(4-methoxyphenyl)acrylate (3n) XG CH otes and references [] X. Li, B. Zhang, Y. Fang, W. Sun, Z. Qi, Y. Pei, S. Qi, P. Yuan, X. Luan, T. W. Goh, W. Huang, Chem. Eur. J. 27, 23, [2] Y. Luan, Y. Qi, H. Gao, R. S. Andriamitantsoa,. Zheng, G. Wang, J. Mater. Chem. A 25, 3, [3] J. B. M. de Resende Filho, G. P. Pires, J. M. G. de liveira Ferreira, E. E. S. Teotonio, J. A. Vale, Catal. Lett. 27, 47, [4] J. Xu, K. Shen, B. Xue, Y.-X. Li, J. Mol. Catal. A: Chem. 23, 372, 5-3. [5] D.-Z. Xu, S. Shi, Y. Wang, RSC Adv. 23, 3, [6] R. Maleki, E. Kolvari, M. Salehi,. Koukabi, Appl. rganomet. Chem. 27,.2/aoc [7] E. M. Schneider, R. A. Raso, C. J. Hofer, M. Zeltner, R. D. Stettler, S. C. Hess, R.. Grass, W. J. Stark, J. rg. Chem. 24, 79, [8] A. Dondoni, A. Massi, Tetrahedron Lett. 2, 42, [9] J. Mondal, T. Sen, A. Bhaumik, Dalton Trans. 22, 4, [] Z.-J. Quan, Y.-X. Da, Z. Zhang, X.-C. Wang, Catal. Commun. 29,, [] X.-L. Shi, H. Yang, M. Tao, W. Zhang, RSC Adv. 23, 3, [2] J. Javidi, M. Esmaeilpour, F.. Dodeji, RSC Adv. 25, 5, [3] A. G. Khiratkar, P.. Muskawar, P. R. Bhagat, RSC Adv. 26, 6, [4] J.-H. Wang, G.-M. Tang, S.-C. Yan, Y.-T. Wang, S.-J. Zhan, E. Zhang, Y. Sun, Y. Jiang, Y.-Z. Cui, Appl. rganomet. Chem. 26, 3, 9-2. [5] B. Dam, A. K. Pal, A. Gupta, Synth. Commun. 26, 46, [6] M. Zeinali-Dastmalbaf, A. Davoodnia, M. M. Heravi,. Tavakoli-Hoseini, A. Khojastehnezhad, H. A. Zamani, Bull. Korean Chem. Soc. 2, 32,
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