Selective N-Alkylation of 2-Amino-4H-chromene-3-carbonitrile Derivatives with Alcohols Catalyzed by AlCl₃ Under the Assistance of CH₃COOH

Abstract

A highly efficient and selective N-alkylation reaction of 2-amino-4H-chromene-3-carbonitrile derivatives using various alcohols as alkylation agent were developed in the presence of AlCl₃ as a catalyst as well as CH₃COOH as an additive, in which the cyano group kept inert and the amino group was alkylated in high yields. All the target products were characterized and determined by infrared(IR), ¹H NMR, ¹³C NMR, and HRMS. And the X-ray structure of product 3ab was obtained. A bimolecular reaction mechanism catalyzed by AlCl₃ was proposed under the assistance of CH₃COOH.

Keywords

N-Alkylation / Alcohol / AlCl₃ / CH₃COOH

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