GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions

Green Chem., 2013, Advance Article
DOI: 10.1039/C3GC41799A, Communication

Huiyan Wang, Xuecheng Liu, Xian Feng, Zhibin Huang, Daqing Shi
This synthesis was confirmed to follow the GAP chemistry process, which can avoid traditional chromatography and recrystallization purification methods.

GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions

http://pubs.rsc.org/en/Content/ArticleLanding/2013/GC/C3GC41799A?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Huiyan Wang,^a^b Xuecheng Liu,^a Xian Feng,^a Zhibin Huang*^a and Daqing Shi*^a

Corresponding authors

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P.R. China

E-mail: zbhuang@suda.edu.cn, dqshi@suda.edu.cn;
Fax: +86-512-65880089

Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, P.R. China

A concise and efficient one-pot synthesis of pyrrolyl coumarin derivatives via a four-component reaction of 4-hydroxycoumarin, arylglyoxal monohydrate, dialkyl but-2-ynedioate and amines under catalyst-free conditions in an environmentally friendly medium (ethanol) is described. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional chromatography and recrystallization purification methods

spectra

R2 = 3 CHLOROPHENYL

R1= METHYL

dimethyl 1-(3-chlorophenyl)-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-phenyl-1H-pyrrole-2, 3-dicarboxylate (5c).

The reaction of 4-hydroxycoumarin 1 (16.2 mg, 1 mmol), phenylflyoxal monohydrate 2a (15.2 mg, 1 mmol), dimethyl but-2-ynedioate 3a (14.2 mg, 1 mmol) and 3-chloroaniline 4c (12.7 mg, 1 mmol) in ethanol (5 mL), at 80 °C 1.5 h, afforded 46.0 mg (87 %) of 5c.
white powder; m.p.: 242-246°C; IR (KBr, ν, cm-1): 3423, 3075, 3002, 2951, 2853, 1720, 1683,
1577, 1483, 1444, 1303, 1271, 1213, 1126, 1077, 1043, 1013, 988, 924, 880, 761, 698, 649; 1
H NMR (DMSO-d6, 400 MHz): δ 11.29 (s, 1H, OH), 7.76 (d, J = 7.6 Hz, 1H, ArH), 7.55 (t, J = 8.0 Hz, 1H, ArH), 7.40-7.18 (m, 6H, ArH), 7.10-7.02 (m, 5H, ArH), 3.63 (s, 3H, OCH3), 3.60 (s, 3H, OCH3); 13C NMR (DMSO-d6, 75 MHz): δ 164.28, 162.30, 162.20, 161.52, 152.91, 139.00,
138.22, 133.24, 132.88, 130.87, 130.27, 129.99, 129.21, 128.80, 128.44, 128.35, 127.59, 127.38,
124.48, 124.09, 119.89, 116.64, 116.16, 113.35, 98.28, 52.89, 52.18; HRMS (ESI) calcdforC29H2035ClNO7 [M]+: 529.0928, found: 529.0933

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