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Synthesis 2023; 55(23): 4011-4019
DOI: 10.1055/a-2156-7470
paper

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

Dongping Cheng∗
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Hongshuang Xia
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Huafang Gu
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Yawei Wang
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Jing-Hua Li∗
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Xiaoliang Xu∗
b   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (22078300).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2156-7470.
  • Supporting Information


Publication History

Received: 19 July 2023

Accepted after revision: 18 August 2023

Accepted Manuscript online:
18 August 2023

Article published online:
27 September 2023

© 2023. Thieme. All rights reserved

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