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Synthesis 2011(10): 1633-1637  
DOI: 10.1055/s-0030-1260003
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of 2-(2-Ethoxy-1,2-dioxoethyl)azoles

Oleksandr V. Geraschenkoa,b, Pavel V. Khodakovskiya, Oleg V. Shishkinc, Pavel K. Mykhailiuk*a,b, Olga A. Zaporozhetsa, Andrey A. Tolmacheva,b
a Enamine Ltd., Oleksandra Matrosova Street 23, Kyiv 01103, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine
Fax: +380(44)2351273; e-Mail: Pavel.Mykhailiuk@gmail.com;
c STC, ‘Institute for Single Crystals’, National Academy of Science of Ukraine, 60 Lenina Ave, Kharkiv 61001, Ukraine
Further Information

Publication History

Received 6 February 2011
Publication Date:
15 April 2011 (online)

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Abstract

C-Acylation of N-substituted imidazoles with ethyl oxalyl chloride in the presence of N,N-diisopropylethylamine as a base afforded 2-(2-ethoxy-1,2-dioxoethyl)imidazoles in 83-95% yield. Application of this synthetic protocol to thiazoles and triazoles led to the corresponding 2-ethoxy-1,2-dioxoethyl derivatives in 40-51% yield.

Key words

azoles - acylations - glyoxylates - keto esters - heterocycles

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