This article is cited in 3 papers

Communications

A cascade formation of N-pyridylacrylamides from pyrido[1,2-a]pyrimidine diones and chromene aldehydes

V. A. Osyanin, I. A. Semenova, A. G. Groshev, D. V. Osipov, Yu. N. Klimochkin

Samara State Technical University, Samara, Russian Federation

Abstract: Various N-(pyridin-2-yl)acrylamides bearing 4H-chromene fragment were synthesized via the condensation of 4H-chromene-3-carbaldehydes and their fused analogues with 2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones employing NH₄OAc/AcOH system. Possible mechanism of this hetero- domino reaction involves the consecutive Knoevenagel condensation, oxa-6v-electrocyclization, aza-6v-electrocyclic ring-opening, nucleophilic addition, retro-Alder-ene reaction and oxa-6v-electrocyclic ring-disclosure.

Keywords: chromene-3-carbaldehydes, pyrido[1, 2-a]pyrimidine-2, 4(3H)-diones, N-(pyridin-2-yl)acrylamides, acrylamides, cascade reaction, electrocyclization, pericyclic reactions.

Language: English

DOI: 10.1016/j.mencom.2021.11.030

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