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Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael-Michael addition.

ABSTRACT: A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followed by the aza-Michael-Michael addition with 2-alkenyl anilines to prepare the tetrahydroquinoline scaffolds.

SUBMITTER: Palanimuthu A

PROVIDER: S-EPMC9051536 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael-Michael addition.

Palanimuthu Arunan A Chen Chinpiao C Lee Gene-Hsian GH

RSC advances 20200403 23

A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followed by the aza-Michael-Michael addition with 2-alkenyl anilines to prepare the tetrahydroquinoline scaffolds. ...[more]

PMID: 35492978

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