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Issue 32, 2014
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One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines

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Abstract

We have described the simple, convenient and high yielding one-pot synthesis of a library of highly functionalized hexa-substituted 1,4-dihydropyridines (1,4-DHPs) by 2-aminopyridine catalysed pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes. This domino transformation involves formation of dihydropyridine ring by creation of two C–C bonds and one C–N bond, all of them taking place in a single synthetic operation. As the products precipitate out of the reaction simple filtration is enough to gather the products and thus, there is no need for work-up or column-chromatography. The C6-methylsulfanyl group in the product 1,4-DHPs was substituted with primary and secondary amines to provide 1,4-DHPs with further possibilities in structural diversity. As a demonstration of application of the method we have synthesised an analogue of nitenpyram, a neonicotinoid insecticide.

Graphical abstract: One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines

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Article information


Submitted
24 Mar 2014
Accepted
05 Jun 2014
First published
05 Jun 2014

Org. Biomol. Chem., 2014,12, 6223-6238
Article type
Paper
Author version available

One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines

H. Surya Prakash Rao and A. Parthiban, Org. Biomol. Chem., 2014, 12, 6223
DOI: 10.1039/C4OB00628C

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