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

Autor:	Christopher Hulme, Mei Yuan Hsu, Justin Dietrich, Arthur Y. Shaw
Rok vydání:	2013
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Imidazole Organic chemistry Cycloaddition
Zdroj:	Synthetic Communications. 43:1538-1542
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397911.2011.644846
Popis:	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.
Databáze:	OpenAIRE
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