Novel approach towards the synthesis of skeletally diverse benzimidazole-pyrrolo[1,2-a]quinoxaline by SNAr/Pictet-Spengler reaction under focused microwave irradiation

Barnali Maiti, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

In a study aimed at developing a novel concise approach to the benzimidazole-pyrrolo[1,2-a]quinoxaline core of medicinal interest, a Pictet-Spengler reaction has been identified that gives direct access to the target compound on soluble polymer support under focused microwave irradiation. The pyrrole moiety has been introduced on polymer immobilized benzimidazole derivatives by SNAr diversification which subsequently transformed to the title compounds via reduction followed by Pictet-Spengler cyclisation with various ketones in good yields and excellent purity. The work described here demonstrates the versatility of the base mediated SNAr reaction coupled with Pictet-Spengler cyclisation in the construction of novel heterocycles.

Original languageEnglish
Pages (from-to)1385-1396
Number of pages12
JournalNew Journal of Chemistry
Volume35
Issue number7
DOIs
StatePublished - 1 Jul 2011

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