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An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles

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Abstract

An unexpected Michael addition-inspired ring-opening/closure cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates was developed to access new dihydrobenzofuran or dihydrobenzothiophene spirooxindoles in 68–98% yields. This reaction not only provides an expedient and convenient method to assemble dihydrobenzofuran spirooxindoles, but also establishes a new reaction mode of coumarin-3-carboxylates. Moreover, it represents the first example of 3-hydroxyoxindoles serving as a C1 synthon possessing dual nucleophilic and electrophilic character with the hydroxyl group as a leaving group. Importantly, this methodology provides a rapid and robust approach to XEN907 analogues.

Graphical abstract: An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles

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Publication details

The article was received on 11 Sep 2019, accepted on 21 Oct 2019 and first published on 21 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC07114H
Chem. Commun., 2019, Advance Article

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    An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles

    K. Zhang, H. Han, L. Wang, Z. Zhang, Q. Wang, W. Zhang and Z. Bu, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC07114H

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