Issue 13, 2025

Efficient construction of spirocyclopentane-1,3-dioxindoles via an annulation reaction of isocyanides and 3-methyleneoxindoles

Abstract

The DABCO-promoted annulation reaction of alkyl isocyanides with two 3-methyleneoxindole molecules in refluxing acetonitrile afforded functionalized dispiro[indoline-3,1′-cyclopentane-3′,3′′-indolines] in moderate yields and with a variety of diastereoselectivities through a cascade [2 + 2 + 1] cycloaddition reaction. However, the DABCO-promoted annulation reaction of 3-(2-isocyanoethyl)indole and 3-phenacylideneoxindoles gave unique polycyclic spiro[indoline-3,5′-pyrrolo[3′,2′:2,3]cyclopenta[1,2-b]indoles] in satisfactory yields and with high diastereoselectivity.

Graphical abstract: Efficient construction of spirocyclopentane-1,3-dioxindoles via an annulation reaction of isocyanides and 3-methyleneoxindoles

Supplementary files

Article information

Article type
Paper
Submitted
05 Feb 2025
Accepted
28 Feb 2025
First published
04 Mar 2025

Org. Biomol. Chem., 2025,23, 3224-3230

Efficient construction of spirocyclopentane-1,3-dioxindoles via an annulation reaction of isocyanides and 3-methyleneoxindoles

L. Huang, W. Ma, J. Sun, Y. Han and C. Yan, Org. Biomol. Chem., 2025, 23, 3224 DOI: 10.1039/D5OB00206K

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