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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.

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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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