期刊
TETRAHEDRON LETTERS
卷 59, 期 27, 页码 2688-2694出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.05.087
关键词
Spiro compounds; Nitrogenheterocycles; Cycloaddition; Azomethine ylides; Multicomponent reactions
资金
- CSIR, New Delhi, India [02 (0218)/14/EMR-II]
- DRDO, New Delhi, India [ERIP/ER/1203083/M/01]
A competent and highly discriminating one-pot synthesis of highly diversified novel functionalized indenoquinoxalone grafted spiropyrrolidine linked chromene-3-carbonitrile conjugates accumulating three pharmocophoric cores, heterocyclic indenoquinoxalone, pyrrolidines and chromene-3-carbonitrile in a single molecular framework by means of 1,3-dipolar cycloaddition reaction between indenoquinoxalone, prolineibenzyl amine and chromene-3-carbonitrile in ethanol under classical and microwave conditions is described. The three component 1,3-dipolar cycloaddition reaction proceeds via in situ generation of azomethine ylides by the decarboxylative condensation of indenoquinoxalone with proline/benzyl amine and their selectivity towards the endo cyclic double bonds of dipolarophile (chromene-3-carbonitrile) leading to the formation of highly functionalised regio- and diastereoselective molecular hybrids. This methodology exemplifies the green chemistry protocol such as mild reaction conditions, high yields, one-pot procedure and operational simplicity. (C) 2018 Elsevier Ltd. All rights reserved.
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