Peculiarities of copper(I)- and palladium-catalyzed cross-coupling of terminal alkynes with vicinal amino- and (N-acetylamino)-iodopyrazoles. Synthesis of alkynylaminopyrazoles

Eugene V. Tretyakov, David W. Knight, Sergei F. Vasilevsky

Результат исследований: Материалы для журналаСтатьярецензирование

41 Цитирования (Scopus)

Аннотация

A number of vicinal amino- and (N-acetylamino)-alkylpyrazoles have been synthesized by cross-coupling reactions of iodopyrazoles with alk-1-ynes using a combination of Pd(PPh3)2Cl2 and CuI as catalyst in Et3N or with copper acetylides. The latter Stephens - Castro reaction of copper acetylides with these amino- and (N-acetylamino)-iodopyrazoles was established as a common method for the preparation of (N-acetylamino)alkynylpyrazoles. The Pd/Cu-catalyzed cross-coupling of iodopyrazoles (Sonogashira reaction) with alk-1-ynes bearing electron-releasing substituents was unsuitable for the synthesis of alkynylpyrazoles: 3- and 5-iodopyrazoles were unreactive but, in the case of 4-iodo derivatives, reductive deiodination, accompanied by homocoupling of the alk-1-yne component, was the only reaction.

Язык оригиналаАнглийский
Страницы (с-по)3713-3720
Число страниц8
ЖурналJournal of the Chemical Society - Perkin Transactions 1
Номер выпуска24
DOI
СостояниеОпубликовано - 21 дек 1999
Опубликовано для внешнего пользованияДа

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Подробные сведения о темах исследования «Peculiarities of copper(I)- and palladium-catalyzed cross-coupling of terminal alkynes with vicinal amino- and (N-acetylamino)-iodopyrazoles. Synthesis of alkynylaminopyrazoles». Вместе они формируют уникальный семантический отпечаток (fingerprint).

Цитировать