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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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Publication details

The article was received on 24 Mar 2014, accepted on 05 Jun 2014 and first published on 05 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB00628C
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 6223-6238
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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

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

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