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Issue 41, 2013
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Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

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Abstract

A novel and catalyst-free aqueous mediated multicomponent domino reaction (MCR) capable of affording medicinally important spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] under sonication in excellent yield and in shorter time is reported. This new protocol provides a new seven-membered ring system selectively instead of the expected five-membered ring system or other possible isomers. The structure and relative stereochemistry of spiro products was established by single crystal X-ray analysis of a representative compound and spectroscopic techniques. In comparison to conventional synthesis, the advantages of this method are that it is catalyst-free, has an easy workup and uses water as the solvent which is considered to be relatively environmentally benign, and this work offers a new way to create molecular complexity with maximum simplicity. The representative compounds were screened for their ability to inhibit the enzyme α-amylase.

Graphical abstract: Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

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Supplementary files

Article information


Submitted
19 Jul 2013
Accepted
23 Jul 2013
First published
02 Sep 2013

RSC Adv., 2013,3, 18992-19001
Article type
Paper

Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

A. Dandia, R. Singh, J. Joshi, S. Maheshwari and P. Soni, RSC Adv., 2013, 3, 18992
DOI: 10.1039/C3RA43745K

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