Synlett 2025; 36(01): 82-86
DOI: 10.1055/a-2294-5395
letter

Copper-Catalyzed [4+1] and [4+2] Reactions through Tandem ­Remote Propargylation/Cyclization/Isomerization with an Amine or a Hydrazine

Yu-Ze Sun
a   Department of Chemistry, Shanghai Normal University, Shanghai 200234, P. R. of China
b   State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
,
Guo-Qiang Lin
a   Department of Chemistry, Shanghai Normal University, Shanghai 200234, P. R. of China
b   State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
,
Zhi-Tao He
c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
d   School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, P. R. of China
e   Ningbo Zhongke Creation Center of New Materials, Ningbo, 315899, P. R. of China
› Author Affiliations
We acknowledge financial support from the National Natural Science Foundation of China (22371292 and 22071262), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB0610000), Natural Science Foundation of Ningbo (2023J036), Shanghai Municipal Committee of Science and Technology (22ZR1475200), the State Key Laboratory of Organometallic Chemistry, and Shanghai Institute of Organic Chemistry.


Abstract

Two novel copper-catalyzed cyclization reactions involving a remote propargylic substitution/cyclization/isomerization cascade are disclosed. Derivatives of the seldomly studied heterocycles thieno[2,3-c]pyrrole and thieno[2,3-d]pyridazine are conveniently synthesized in moderate to good yields from primary amines or arylhydrazines through [4+1] and [4+2] reactions, respectively. Preliminary mechanistic experiments corroborated the occurrence of the designed cascade reactions.

Supporting Information



Publication History

Received: 29 February 2024

Accepted after revision: 25 March 2024

Accepted Manuscript online:
25 March 2024

Article published online:
15 April 2024

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