REGIOSELECTIVE SYNTHESIS OF EITHER 1H- OR 2H-1,2,3- TRIAZOLES VIA MICHAEL ADDITION TO α,ß-UNSATURATED KETONES.

doi:10.3987/COM-08-S(N)73

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REGIOSELECTIVE SYNTHESIS OF EITHER 1H- OR 2H-1,2,3- TRIAZOLES VIA MICHAEL ADDITION TO α,ß-UNSATURATED KETONES.

S. W. Kwok, J. Hein, V. Fokin

Nov 1, 2008

Citations

Journal

Heterocycles

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Semantic Scholar

Key Takeaway

Key Takeaway: Selective synthesis of either 1H-1,2,3-triazoles or 2H-regioisomers of 1,3-triazolyl ketones can be achieved through Michael addition to,-unsaturated ketones.

Abstract

The Michael reaction of NH-1,2,3-triazole (1) with α,β-unsaturated ketones was studied. 1H-1,2,3-triazolyl-ketones were selectively generated when 1 was combined neat with a variety of enones. The use of aprotic solvents with catalytic base gave the corresponding 2H-regioisomers. Together, these two protocols provide direct access to either the N1- or N2-substituted 1,3-triazolyl ketone regioisomers.

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