Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazoles

Shin Kamijo, Zhibao Huo, Tetsuo Kin, Chikashi Kanazawa, Yoshinori Yamamoto

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26 Citations (Scopus)

Abstract

Two facile deallylation protocols have been developed for the preparation of N-unsubstituted triazoles and tetrazoles. The first protocol is a direct deallylation using a combination of a catalytic amount of nickel complex, NiCl2(dppe), and a stoichiometric amount of Grignard reagent, tBuMgCl. The second protocol is a stepwise deallylation through consecutive reactions of isomerization and ozonolysis. The isomerization from N-allylazoles to N-vinylazoles is catalyzed by a ruthenium complex, HRuCl(CO)(PPh3)3, and the following ozonolysis of the derived N-vinyl intermediates affords N-unsubstituted azoles. These protocols can be used complementarily depending on the type of functional groups in the parent allylated azoles.

Original languageEnglish
Pages (from-to)6389-6397
Number of pages9
JournalJournal of Organic Chemistry
Volume70
Issue number16
DOIs
Publication statusPublished - 2005 Aug 5

ASJC Scopus subject areas

  • Organic Chemistry

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