A Convenient Preparation of 2-Aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and Their Application in the Synthesis of 5-Aroyl-2-oxo-1,2-dihydro-2-pyridinecarbonitriles

Engoor R. Anabha; Chittoorthekkathil V. Asokan

doi:10.1055/s-2005-918491

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A Convenient Preparation of 2-Aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and Their Application in the Synthesis of 5-Aroyl-2-oxo-1,2-dihydro-2-pyridinecarbonitriles

Engoor R. Anabha, Chittoorthekkathil V. Asokan*
School of Chemical Sciences, Mahatma Gandhi University, Priyadarshini Hills P. O., Kottayam 686 560, India
Fax: +91(481)2731009; e-Mail: asokancv@yahoo.com;

Abstract

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Abstract

The reaction of aroylketene dithioacetals 1 with Vilsmeier-Haack reagent, prepared from POCl₃ and DMF, under mild conditions gave 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes 2 in excellent yields. Cyclization of 2-[2-aroyl-3,3-bis(methylsulfanyl)-2-propylidene]malononitriles 3, derived from 2 and malononitrile, in the presence of concentrated hydrochloric acid in tertiary butanol afforded 2-pyridone derivatives 4.

Key words

ketene dithioacetals - Knoevenagel condensations - cyclizations - Vilsmeier-Haack reactions - 2-pyridones

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References

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