Synthesis of Pyrido[2,3-d]pyrimidines Catalyzed by 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-Butyl Nitrite (TBN)/O₂

Abstract

Catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-butyl nitrite (TBN)/O₂, an efficient tandem oxidative reaction of uracils/thiouracil with 1,3-diarylpropenes is disclosed. It undergoes oxidative coupling, intramolecular cyclization, and dehydro-aromatization to provide multi-substituted pyrido[2,3-d]pyrimidines/thiopyrido[2,3-d]pyrimidines in moderate to excellent yields. It has the advantages of high atom economy, green terminal oxidant, and metal-free conditions.

Key words

pyrido[2,3-d]pyrimidine - oxidative coupling reaction - DDQ - tandem reaction - uracil

Publication History

Received: 19 July 2023

Accepted after revision: 18 August 2023

Accepted Manuscript online:
18 August 2023

Article published online:
27 September 2023

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