<\/h5>\n\n\n![\"\"](\"http:\/\/pubs.rsc.org\/services\/images\/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc\/ImageService\/image\/GA?id=C3GC41799A\")
<\/p>\n<\/div>\n
Green Chem.<\/b><\/i>, 2013, Advance Article
\nDOI<\/b>: 10.1039\/C3GC41799A, Communication<\/div>\nHuiyan Wang, Xuecheng Liu, Xian Feng, Zhibin Huang, Daqing Shi
\nThis synthesis was confirmed to follow the GAP chemistry process, which can avoid traditional chromatography and recrystallization purification methods.<\/div>\n\nGAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions<\/a><\/h4>\nhttp:\/\/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<\/a><\/p>\nHuiyan Wang<\/a>,a<\/sup>b<\/sup>\u00a0\u00a0\u00a0Xuecheng Liu<\/a>,a<\/sup>\u00a0\u00a0\u00a0Xian Feng<\/a>,a<\/sup>\u00a0\u00a0Zhibin Huang<\/a>*a<\/sup>\u00a0and\u00a0\u00a0\u00a0Daqing Shi<\/a>*a<\/sup><\/div>\n<\/div>\n*<\/p>\n\nCorresponding authors<\/div>\n<\/div>\n<\/div>\n\n\na<\/sup>Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P.R. China<\/div>\nE-mail:\u00a0<\/b>zbhuang@suda.edu.cn<\/a>,\u00a0dqshi@suda.edu.cn<\/a>;
\nFax:\u00a0<\/b>+86-512-65880089<\/div>\n<\/div>\n\nb<\/sup><\/div>\nDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, P.R. China<\/div>\n<\/div>\n<\/div>\nA concise and efficient one-pot synthesis of pyrrolyl coumarin derivatives\u00a0via<\/em>\u00a0a 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<\/p>\nspectra<\/p>\n
R2 \u00a0= 3 CHLOROPHENYL<\/p>\n
R1= METHYL<\/p>\n
dimethyl 1-(3-chlorophenyl)-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-phenyl-1H-pyrrole-2, 3-dicarboxylate (5c).<\/p>\n
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 \u00b0C 1.5 h, afforded 46.0 mg (87 %) of 5c.
\nwhite powder; m.p.: 242-246\u00b0C; IR (KBr, \u03bd, cm-1): 3423, 3075, 3002, 2951, 2853, 1720, 1683,
\n1577, 1483, 1444, 1303, 1271, 1213, 1126, 1077, 1043, 1013, 988, 924, 880, 761, 698, 649; 1
\nH NMR (DMSO-d6, 400 MHz): \u03b4 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): \u03b4 164.28, 162.30, 162.20, 161.52, 152.91, 139.00,
\n138.22, 133.24, 132.88, 130.87, 130.27, 129.99, 129.21, 128.80, 128.44, 128.35, 127.59, 127.38,
\n124.48, 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<\/p>\n
http:\/\/www.rsc.org\/suppdata\/gc\/c3\/c3gc41799a\/c3gc41799a.pdf<\/a><\/p>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":"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,ab\u00a0\u00a0\u00a0Xuecheng Liu,a\u00a0\u00a0\u00a0Xian… Continue reading GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[11],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=1172"}],"version-history":[{"count":4,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172\/revisions"}],"predecessor-version":[{"id":1176,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172\/revisions\/1176"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=1172"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=1172"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=1172"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}
<\/p>\n<\/div>\n
\nDOI<\/b>: 10.1039\/C3GC41799A, Communication<\/div>\n
\nThis synthesis was confirmed to follow the GAP chemistry process, which can avoid traditional chromatography and recrystallization purification methods.<\/div>\n
GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions<\/a><\/h4>\nhttp:\/\/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<\/a><\/p>\nHuiyan Wang<\/a>,a<\/sup>b<\/sup>\u00a0\u00a0\u00a0Xuecheng Liu<\/a>,a<\/sup>\u00a0\u00a0\u00a0Xian Feng<\/a>,a<\/sup>\u00a0\u00a0Zhibin Huang<\/a>*a<\/sup>\u00a0and\u00a0\u00a0\u00a0Daqing Shi<\/a>*a<\/sup><\/div>\n<\/div>\n*<\/p>\n\nCorresponding authors<\/div>\n<\/div>\n<\/div>\n\n\na<\/sup>Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P.R. China<\/div>\nE-mail:\u00a0<\/b>zbhuang@suda.edu.cn<\/a>,\u00a0dqshi@suda.edu.cn<\/a>;
\nFax:\u00a0<\/b>+86-512-65880089<\/div>\n<\/div>\n\nb<\/sup><\/div>\nDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, P.R. China<\/div>\n<\/div>\n<\/div>\nA concise and efficient one-pot synthesis of pyrrolyl coumarin derivatives\u00a0via<\/em>\u00a0a 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<\/p>\nspectra<\/p>\n
R2 \u00a0= 3 CHLOROPHENYL<\/p>\n
R1= METHYL<\/p>\n
dimethyl 1-(3-chlorophenyl)-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-phenyl-1H-pyrrole-2, 3-dicarboxylate (5c).<\/p>\n
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 \u00b0C 1.5 h, afforded 46.0 mg (87 %) of 5c.
\nwhite powder; m.p.: 242-246\u00b0C; IR (KBr, \u03bd, cm-1): 3423, 3075, 3002, 2951, 2853, 1720, 1683,
\n1577, 1483, 1444, 1303, 1271, 1213, 1126, 1077, 1043, 1013, 988, 924, 880, 761, 698, 649; 1
\nH NMR (DMSO-d6, 400 MHz): \u03b4 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): \u03b4 164.28, 162.30, 162.20, 161.52, 152.91, 139.00,
\n138.22, 133.24, 132.88, 130.87, 130.27, 129.99, 129.21, 128.80, 128.44, 128.35, 127.59, 127.38,
\n124.48, 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<\/p>\n
http:\/\/www.rsc.org\/suppdata\/gc\/c3\/c3gc41799a\/c3gc41799a.pdf<\/a><\/p>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":"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,ab\u00a0\u00a0\u00a0Xuecheng Liu,a\u00a0\u00a0\u00a0Xian… Continue reading GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[11],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=1172"}],"version-history":[{"count":4,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172\/revisions"}],"predecessor-version":[{"id":1176,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172\/revisions\/1176"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=1172"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=1172"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=1172"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}
\nFax:\u00a0<\/b>+86-512-65880089<\/div>\n<\/div>\n
A concise and efficient one-pot synthesis of pyrrolyl coumarin derivatives\u00a0via<\/em>\u00a0a 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<\/p>\n spectra<\/p>\n R2 \u00a0= 3 CHLOROPHENYL<\/p>\n R1= METHYL<\/p>\n dimethyl 1-(3-chlorophenyl)-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-phenyl-1H-pyrrole-2, 3-dicarboxylate (5c).<\/p>\n 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 \u00b0C 1.5 h, afforded 46.0 mg (87 %) of 5c. http:\/\/www.rsc.org\/suppdata\/gc\/c3\/c3gc41799a\/c3gc41799a.pdf<\/a><\/p>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":" 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,ab\u00a0\u00a0\u00a0Xuecheng Liu,a\u00a0\u00a0\u00a0Xian… Continue reading GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[11],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=1172"}],"version-history":[{"count":4,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172\/revisions"}],"predecessor-version":[{"id":1176,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/1172\/revisions\/1176"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=1172"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=1172"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=1172"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}
\nwhite powder; m.p.: 242-246\u00b0C; IR (KBr, \u03bd, cm-1): 3423, 3075, 3002, 2951, 2853, 1720, 1683,
\n1577, 1483, 1444, 1303, 1271, 1213, 1126, 1077, 1043, 1013, 988, 924, 880, 761, 698, 649; 1
\nH NMR (DMSO-d6, 400 MHz): \u03b4 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): \u03b4 164.28, 162.30, 162.20, 161.52, 152.91, 139.00,
\n138.22, 133.24, 132.88, 130.87, 130.27, 129.99, 129.21, 128.80, 128.44, 128.35, 127.59, 127.38,
\n124.48, 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<\/p>\n