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Synthesis 2023; 55(10): 1561-1569
DOI: 10.1055/a-1994-8251
paper

Synthesis of Spiro[benzofuran-2,3′-pyrazol]-3-imines from Aurone-Derived Azadienes and Hydrazonoyl Chlorides via Regio- and Diastereospecific [2+3] Cycloaddition

Dilnigar Askar‡
a   College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, P. R. of China
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
c   Shenzhen Lifotronic Technology CO., Ltd., Shenzhen 518055, P. R. of China
,
Xiancheng Liu‡
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
c   Shenzhen Lifotronic Technology CO., Ltd., Shenzhen 518055, P. R. of China
,
Ablikim Obolda∗
a   College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, P. R. of China
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
,
Wei Xu∗
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
,
Yan Xu
c   Shenzhen Lifotronic Technology CO., Ltd., Shenzhen 518055, P. R. of China
,
Guixue Wang
d   College of Bioengineering, Chongqing University, Chongqing 400044, P. R. of China
,
Taimin Wang
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
,
Hongbin Zhai
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
e   State Key Laboratory of Chemical Oncogenomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China
,
Bin Cheng∗
a   College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, P. R. of China
b   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
› InstitutsangabenWe thank the National Natural Science Foundation of China (NSFC) (Nos. 21971092 and 21901014), the Innovation Platform for the Integration of Production and Education of Guangdong Education Department (No. 2021CJPT014), the Innovation Team of Guangdong Education Department (No. 2022KCXTD054), the Shenzhen Science and Technology Innovation Committee (Nos. JSGG20201103153800002, JCYJ20200109141808025, and GJHZ20200731095412037), and the Post-doctoral Foundation Project of Shenzhen Polytechnic (No. 6021330005K) for financial support.
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Abstract

An array of spiro[benzofuran-2,3′-pyrazol]-3-imines with diverse functional groups were readily assembled from aurone-derived azadienes and in-situ generated nitrilimines under mild conditions. The transformation was performed in a regio- and diastereoselective fashion, in which a synergetic [2+3] cycloaddition pathway was likely involved. This novel methodology has extended the synthetic application of aurone-derived azadienes as a kind of two-atom synthon.

Key words

spiro[benzofuran-2,3′-pyrazol]-3-imines - aurone-derived azadienes - hydrazonoyl chlorides - nitrilimines - [2+3] cycloaddition

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1994-8251.
  • Supporting Information


Publikationsverlauf

Eingereicht: 28. Oktober 2022

Angenommen nach Revision: 08. Dezember 2022

Accepted Manuscript online:
08. Dezember 2022

Artikel online veröffentlicht:
19. Januar 2023

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