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Issue 4, 2014
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Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(iii)-catalyzed regioselective 6-endo-dig ring closure

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Abstract

An operationally simple approach for the stereoselective tandem synthesis of novel thiazolo fused naphthyridines 5a–o and thienopyridines 8a–e by the reaction of o-alkynylaldehydes with L-cystine methyl ester hydrochloride via Au(III)-catalyzed regioselective 6-endo-dig ring closure under mild reaction conditions is described. It is noteworthy that alkynes bearing an alkyl and a strong electron-withdrawing nitro group successfully afforded the desired products in good yields.

Graphical abstract: Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(iii)-catalyzed regioselective 6-endo-dig ring closure

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Article information


Submitted
11 Oct 2013
Accepted
08 Nov 2013
First published
08 Nov 2013

Org. Biomol. Chem., 2014,12, 552-556
Article type
Communication

Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(III)-catalyzed regioselective 6-endo-dig ring closure

R. R. Jha, R. K. Saunthwal and A. K. Verma, Org. Biomol. Chem., 2014, 12, 552
DOI: 10.1039/C3OB42035C

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