Microwave-Assisted Synthesis of Benzimidazole-Linked Indoline and Indole Hybrids from C-2 Linked (o-Aminobenzyl)benzimidazoles

Yun Ta Lee; Feng Yu Chiu; Indrajeet J. Barve; Chung-Ming Sun

doi:10.1002/adsc.201701140

Microwave-Assisted Synthesis of Benzimidazole-Linked Indoline and Indole Hybrids from C-2 Linked (o-Aminobenzyl)benzimidazoles

Yun Ta Lee, Feng Yu Chiu, Indrajeet J. Barve, Chung-Ming Sun^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

An efficient and novel synthesis of benzimidazole-linked indoline hybrids via an unconventional Pictet-Spengler-type condensation of C-2 linked (o-aminobenzyl)benzimidazoles with aldehydes and ketones under microwave irradiation has been explored. The key condensation step consists of acid-catalyzed imine generation followed by intramolecular C–C bond formation through unique reactivity of the benzimidazole moiety. The scope of this method is further extended to synthesize tetracyclic pyrroloindole benzimidazole-carboxylates through 2-carboxaldehydes. (Figure presented.).

Original language	English
Pages (from-to)	502-512
Number of pages	11
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	3
DOIs	https://doi.org/10.1002/adsc.201701140
State	Published - 1 Feb 2018

Keywords

benzimidazole-linked indoles
benzimidazole-linked indolines
indoline synthesis
pyrroloindolebenzimidazole-carboxylates
unconventional Pictet–Spengler reaction

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10.1002/adsc.201701140

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title = "Microwave-Assisted Synthesis of Benzimidazole-Linked Indoline and Indole Hybrids from C-2 Linked (o-Aminobenzyl)benzimidazoles",

abstract = "An efficient and novel synthesis of benzimidazole-linked indoline hybrids via an unconventional Pictet-Spengler-type condensation of C-2 linked (o-aminobenzyl)benzimidazoles with aldehydes and ketones under microwave irradiation has been explored. The key condensation step consists of acid-catalyzed imine generation followed by intramolecular C–C bond formation through unique reactivity of the benzimidazole moiety. The scope of this method is further extended to synthesize tetracyclic pyrroloindole benzimidazole-carboxylates through 2-carboxaldehydes. (Figure presented.).",

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AU - Chiu, Feng Yu

AU - Barve, Indrajeet J.

AU - Sun, Chung-Ming

PY - 2018/2/1

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N2 - An efficient and novel synthesis of benzimidazole-linked indoline hybrids via an unconventional Pictet-Spengler-type condensation of C-2 linked (o-aminobenzyl)benzimidazoles with aldehydes and ketones under microwave irradiation has been explored. The key condensation step consists of acid-catalyzed imine generation followed by intramolecular C–C bond formation through unique reactivity of the benzimidazole moiety. The scope of this method is further extended to synthesize tetracyclic pyrroloindole benzimidazole-carboxylates through 2-carboxaldehydes. (Figure presented.).

AB - An efficient and novel synthesis of benzimidazole-linked indoline hybrids via an unconventional Pictet-Spengler-type condensation of C-2 linked (o-aminobenzyl)benzimidazoles with aldehydes and ketones under microwave irradiation has been explored. The key condensation step consists of acid-catalyzed imine generation followed by intramolecular C–C bond formation through unique reactivity of the benzimidazole moiety. The scope of this method is further extended to synthesize tetracyclic pyrroloindole benzimidazole-carboxylates through 2-carboxaldehydes. (Figure presented.).

KW - benzimidazole-linked indoles

KW - benzimidazole-linked indolines

KW - indoline synthesis

KW - pyrroloindolebenzimidazole-carboxylates

KW - unconventional Pictet–Spengler reaction

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DO - 10.1002/adsc.201701140

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Microwave-Assisted Synthesis of Benzimidazole-Linked Indoline and Indole Hybrids from C-2 Linked (o-Aminobenzyl)benzimidazoles

Abstract

Keywords

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