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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 11
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Original Articles

Synthesis of Di- and Tri-Substituted Imidazole-4-carboxylates via PBu3-Mediated [3 + 2] Cycloaddition

, , &
Pages 1538-1542 | Received 30 Oct 2011, Published online: 06 Mar 2013
 

Abstract

Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole-4-carboxylates stemmed from the PBu3-mediated [3 + 2] cycloaddition between in situ–generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7–20 were afforded in better yields than those of disubstituted imidazoles 21–27.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

Financial support from the National Science Council of the Republic of China to A. Y. S. is gratefully acknowledged.

Notes

a Yield refers to two-step isolated 7 from amidoacetic acid 3a.

b The product was not found.

a One-pot, two-step isolated yield.

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