Novel synthesis of highly functionalized pyrazolines and pyrazoles by triphenylphosphine mediated reaction of dialkyl azodicarboxylate with allenic esters

TitleNovel synthesis of highly functionalized pyrazolines and pyrazoles by triphenylphosphine mediated reaction of dialkyl azodicarboxylate with allenic esters
Publication TypeJournal Article
Year of Publication2006
AuthorsNair, V, Biju, AT, Mohanan, K, Eringathodi, S
JournalOrganic Letters
Volume8
Issue11
Pagination2213–2216
Date PublishedMAY
Type of ArticleArticle
Abstract

Reaction of the Huisgen zwitterion, derived from triphenylphosphine and dialkyl azodicarboxylate, with allenic esters affords highly functionalized pyrazolines and pyrazoles. The crystal structure of pyrazoline derivative 7a showed extensive C−H···O interactions. Pyrazole formation proceeds via a novel nitrogen to carbon migration of the carboalkoxy group.

DOI10.1021/ol0604623
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.732

Divison category: 
Organic Chemistry