Rapid two-step synthesis of benzimidazo[1′,2′:1,5]pyrrolo[2,3- c ]isoquinolines by a three-component coupling reaction

Bharat D. Narhe; Min Huan Tsai; Chung-Ming Sun

doi:10.1021/co500049r

Rapid two-step synthesis of benzimidazo[1′,2′:1,5]pyrrolo[2,3- c ]isoquinolines by a three-component coupling reaction

Bharat D. Narhe, Min Huan Tsai, Chung-Ming Sun^*

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17 引文斯高帕斯（Scopus）

摘要

A two-step, three-component coupling reaction on ionic liquid supported 2-cyanomethylbenzimidazoles, methyl 2-formylbenzoate, and isocyanides under microwave activation is explored. Knoevenagel condensation of 2-cyanomethylbenzimidazole with methyl-2-formylbenzoate in the presence of piperidine catalyst is followed by [4 + 1] cycloaddition with an isocyanide in the next step. Consequent intramolecular δ-lactam formation allows rapid construction of novel aza-pentacycles, benzimidazo[1′,2′:1,5] pyrrolo[2,3-c]isoquinolines.

原文	English
頁（從 - 到）	421-427
頁數	7
期刊	ACS Combinatorial Science
卷	16
發行號	8
DOIs	https://doi.org/10.1021/co500049r
出版狀態	Published - 11 8月 2014

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10.1021/co500049r

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title = "Rapid two-step synthesis of benzimidazo[1′,2′:1,5]pyrrolo[2,3- c ]isoquinolines by a three-component coupling reaction",

abstract = "A two-step, three-component coupling reaction on ionic liquid supported 2-cyanomethylbenzimidazoles, methyl 2-formylbenzoate, and isocyanides under microwave activation is explored. Knoevenagel condensation of 2-cyanomethylbenzimidazole with methyl-2-formylbenzoate in the presence of piperidine catalyst is followed by [4 + 1] cycloaddition with an isocyanide in the next step. Consequent intramolecular δ-lactam formation allows rapid construction of novel aza-pentacycles, benzimidazo[1′,2′:1,5] pyrrolo[2,3-c]isoquinolines.",

keywords = "benzimidazo[1′,2′:1,5]pyrrolo[2,3- c ]isoquinolines, ionic liquid support, microwave, pyrrolo[1,2- a ]benzimidazole",

author = "Narhe, {Bharat D.} and Tsai, {Min Huan} and Chung-Ming Sun",

year = "2014",

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AU - Narhe, Bharat D.

AU - Tsai, Min Huan

AU - Sun, Chung-Ming

PY - 2014/8/11

Y1 - 2014/8/11

N2 - A two-step, three-component coupling reaction on ionic liquid supported 2-cyanomethylbenzimidazoles, methyl 2-formylbenzoate, and isocyanides under microwave activation is explored. Knoevenagel condensation of 2-cyanomethylbenzimidazole with methyl-2-formylbenzoate in the presence of piperidine catalyst is followed by [4 + 1] cycloaddition with an isocyanide in the next step. Consequent intramolecular δ-lactam formation allows rapid construction of novel aza-pentacycles, benzimidazo[1′,2′:1,5] pyrrolo[2,3-c]isoquinolines.

AB - A two-step, three-component coupling reaction on ionic liquid supported 2-cyanomethylbenzimidazoles, methyl 2-formylbenzoate, and isocyanides under microwave activation is explored. Knoevenagel condensation of 2-cyanomethylbenzimidazole with methyl-2-formylbenzoate in the presence of piperidine catalyst is followed by [4 + 1] cycloaddition with an isocyanide in the next step. Consequent intramolecular δ-lactam formation allows rapid construction of novel aza-pentacycles, benzimidazo[1′,2′:1,5] pyrrolo[2,3-c]isoquinolines.

KW - benzimidazo[1′,2′:1,5]pyrrolo[2,3- c ]isoquinolines

KW - ionic liquid support

KW - microwave

KW - pyrrolo[1,2- a ]benzimidazole

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Rapid two-step synthesis of benzimidazo[1′,2′:1,5]pyrrolo[2,3- c ]isoquinolines by a three-component coupling reaction

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