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Synthesis 2023; 55(03): 457-464
DOI: 10.1055/a-1942-7191
paper

Na2CO3-Mediated [3+3] Annulation Reaction of Substituted Benzamidines with 2-Benzylidenemalononitriles: Access to Substituted Pyrimidine-4,6-diamines

Chengjun Wu
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China
,
Xiaoqin Bian
b   School of Pharmacy, Taizhou Polytechnic College, Taizhou 225300, P. R. of China
,
Lizhong Wang
b   School of Pharmacy, Taizhou Polytechnic College, Taizhou 225300, P. R. of China
,
Yue Zhang
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China
,
Cunde Wang  ∗
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China
› Author AffiliationsThis research was financially supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions.
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Abstract

An efficient protocol for the synthesis of 2-aryl-5-benzyl­pyrimidine-4,6-diamines from readily available substituted 2-benzyl­idenemalononitriles and substituted benzamidines was developed. This practical protocol provides high value pyrimidine-4,6-diamines in moderate to good yields under simple reaction conditions. This approach also enables some modifications of structurally complex bioactive molecules and exhibits potential applications in medicinal chemistry.

Key words

4,6-diaminopyrimidines - 2-benzylidenemalononitriles - benz­amidines - annulation reaction - N-heterocycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1942-7191.
  • Supporting Information


Publication History

Received: 07 August 2022

Accepted after revision: 14 September 2022

Accepted Manuscript online:
14 September 2022

Article published online:
24 October 2022

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