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

New Journal of Chemistry Pub Date: 2011-04-12 DOI: 10.1039/C1NJ20153K

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 viareduction 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.

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