A facile and convenient reaction of o-alkynylisocyanobenzenes with various active methylene compounds, including 1,3-diesters, 1,3-diketones, β-keto esters and a β-keto amide, under Brønsted basic conditions was developed. Diethyl malonate smoothly undergoes the reaction with a collection of o-alkynylisocyanobenzenes to provide the corresponding 2-quinolin-2-yl malonates in excellent yields. Acetylacetone yields a mixture of quinolin-4-yl and quinolin-2-yl derivatives. Acetoacetate esters and acetoacetyl amide derivative give primarily formed 2-quinolin-2-yl adducts which partially undergo deacetylation under the reaction conditions.
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