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; Hongshuang Xia; Huafang Gu; Yawei Wang; Jing-Hua Li; Xiaoliang Xu

doi:10.1055/a-2156-7470

Synthesis, Table of Contents

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∗

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Hongshuang Xia

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Huafang Gu

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Yawei Wang

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Jing-Hua Li∗

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Xiaoliang Xu∗

^bCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

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Abstract

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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

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References

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