The preparation of functionalized amines and amides using benzotriazole derivatives and organozinc reagents

doi:10.1016/S0040-4020(98)00353-6

Tetrahedron

Volume 54, Issue 25, 18 June 1998, Pages 7167-7178

Dedicated to our friend Professor Madeleine Joullie in celebration of 40 years of distinguished teaching and research at the University of Pennsylvania.

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Abstract

Secondary and tertiary amines 6 are conveniently prepared in good yields by reacting organozinc halides with adducts 4, which are derived from the corresponding amines, aldehydes and benzotriazole. The use of organozinc reagents enables the introduction of nitro, cyano or ester functionalities into amine mainframes. This methodology was also used to prepare functionalized amides 8.

The reactions of organozinc halides with benzotriazole derivatives 1 enable the introduction of nitro, cyano or ester functionalities into secondary and tertiary amine or amide mainframes 2.

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The preparation of functionalized amines and amides using benzotriazole derivatives and organozinc reagents

Abstract

Tetrahedron

Tetrahedron Lett.

Tetrahedron

Biological Formation and Reactions of the Amido Group

J. Org. Chem.

Synthesis

J. Chem. Soc., Perkin Trans. 1

J. Org. Chem.

Chem. Rev.

J. Chem. Soc., Perkin Trans. 1