Synthesis 2024; 56(24): 3915-3922
DOI: 10.1055/a-2445-1338
paper

Concise Synthesis of Tetrasubstituted 1,6-Dihydropyridazine and Pyridazine Derivatives

Juan Zhang
a   School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. of China
,
Haiyan Zhang
a   School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. of China
,
Zhen Wang
b   School of Pharmaceutical Sciences and Chongqing Key Laboratory of Natural Drug Research, Chongqing University, Chongqing 40133, P. R. of China
,
Weijun Yao
a   School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. of China
› Author Affiliations
We gratefully acknowledge the Natural Science Foundation of Zhejiang Province (Grant LTZ22B020002), and the Natural Science Foundation of Chongqing (cstc2020jcyj-msxmX0720) for the financial support of this work.


Abstract

A novel one-pot three-steps process has been developed, including phosphine-catalyzed Rauhut–Currier reaction of γ-alkyl allenoates, Diels–Alder reaction with di-tert-butyl azodicarboxylate, followed by deprotection of Boc group to prepare tetra-substituted 1,6-dihydropyridazines in good yields. The 1,6-dihydropyridazines were easily converted to pyridazine derivatives via oxidative aromatization by DDQ.

Supporting Information



Publication History

Received: 12 August 2024

Accepted after revision: 17 October 2024

Accepted Manuscript online:
17 October 2024

Article published online:
11 November 2024

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