Facile Deallylation Protocols for the Preparation of N-Unsubstituted Triazoles and Tetrazoles
- 7 July 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (16), 6389-6397
- https://doi.org/10.1021/jo050836q
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.Keywords
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