Journal
ACS COMBINATORIAL SCIENCE
Volume 13, Issue 1, Pages 65-71Publisher
AMER CHEMICAL SOC
DOI: 10.1021/co100022h
Keywords
natural product inspired synthesis; diversity oriented synthesis; antitubercular agent; tetrahydroquinoline; benzopyran; cellulose sulfuric acid
Funding
- CSIR-UGC New Delhi
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An efficient natural product inspired diversity oriented synthesis of tetrahydroquinoline analogues has been developed using the natural carbohydrate derived solid acid catalyst via multicomponent aza-Diels-Alder reaction of imine (generated in situ from aromatic amine and aldehyde) with dienophile in acetonitrile in a diastereoselective manner. The use of water as solvent reverses the diastereoselectivity toward the cis isomer. Interestingly, tricyclic pyrano/furano benzopyran with cis diastereoselectivity is obtained when salicylaldehyde is used as an alternative of aromatic aldehyde under the same condition. These synthesized quinolines and benzopyrans analogues have been evaluated for their Antitubercular activity against M. tuberculosis H37Ra, and M. tuberculosis H(37)Rv, and some of the analogues shows better activity profile than their natural product analogues. The protocol is not only mild, efficient, ecofriendly, but also involves reusable and biodegradable catalyst and provides route for both the diastereoisomer.
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