Novel reaction of the “huisgen zwitterion” with chalcones and dienones: an efficient strategy for the synthesis of pyrazoline and pyrazolopyridazine derivatives

TitleNovel reaction of the “huisgen zwitterion” with chalcones and dienones: an efficient strategy for the synthesis of pyrazoline and pyrazolopyridazine derivatives
Publication TypeJournal Article
Year of Publication2007
AuthorsNair, V, Biju, AT, Mathew, SC, Eringathodi, S
JournalAngewandte Chemie-International Edition
Volume46
Issue12
Pagination2070–2073
Date PublishedMAR
Type of ArticleArticle
Keywordschalcones; nitrogen heterocycles; pyrazolines; synthetic methods; zwitterions
Abstract

Two unexpected transformations: The reaction of the Huisgen zwitterion derived from triphenylphosphane and diisopropyl azodicarboxylate (DIAD) with chalcones affords functionalized pyrazolines. In contrast, the reaction with dienones affords pyrazolopyridazines, presumably by Diels–Alder reaction of the initially formed pyrazoline with excess DIAD (see scheme).

DOI10.1002/anie.200604025
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

11.709

Divison category: 
Organic Chemistry