Synthesis 2022; 54(10): 2423-2432
DOI: 10.1055/a-1731-2703
paper

N-Iodosuccinimide-Promoted Selective Construction of Cyclopropyl and Dihydrofuranyl Spirooxindoles from Alkylidene Oxindoles and Annular β-Dicarbonyl Compounds

Hong Chen
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Hui Xu
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Zeng-Yang He
b   Technology Center, China Tobacco Anhui Industrial Co., Ltd., 9 Tianda Road, Hefei 230088, P. R. of China
,
Peng Zou
b   Technology Center, China Tobacco Anhui Industrial Co., Ltd., 9 Tianda Road, Hefei 230088, P. R. of China
,
Fei-Hong Huang
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Ying Jin
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Ze Zhang
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
› Institutsangaben
This work was supported by the Natural Science Foundation of Anhui Province (2008085QB64), Foundation of Anhui Province Key Laboratory of Clean Energy Materials and Chemistry for Sustainable Conversion of Natural Resources (LCECSC-15), Pre-research Project of National Natural Science Foundation of Anhui Polytechnic University (Xjky2020079, 2019yyzr09), Foundation of China Tobacco Anhui Industrial Corporation (2020146) and Foundation of China National Tobacco Corporation (11201903003).


Abstract

An efficient N-iodosuccinimide-promoted cyclization of readily available alkylidene oxindoles with annular β-dicarbonyl compounds has been demonstrated. With five-membered cyclic β-dicarbonyl compounds as the starting materials, a series of cyclopropyl oxindoles can be obtained in good to excellent yields, whereas the method affords dihydrofuranyl spirooxindoles almost quantitatively when six- or seven-membered cyclic β-dicarbonyl compounds are employed. This protocol provides a new alternative to the practical synthesis of structurally diverse spirooxindoles.

Supporting Information



Publikationsverlauf

Eingereicht: 18. November 2021

Angenommen nach Revision: 04. Januar 2022

Accepted Manuscript online:
04. Januar 2022

Artikel online veröffentlicht:
21. Februar 2022

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