A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1 H-pyrrole-2,3-diones with diazooxindoles

Pavel A Topanov; Anna A Maslivets; Maksim V Dmitriev; Irina V Mashevskaya; Yurii V Shklyaev; Andrey N Maslivets

doi:10.3762/bjoc.18.162

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1 H-pyrrole-2,3-diones with diazooxindoles

Beilstein J Org Chem. 2022 Nov 10:18:1532-1538. doi: 10.3762/bjoc.18.162. eCollection 2022.

Authors

Pavel A Topanov^{1

2}, Anna A Maslivets², Maksim V Dmitriev², Irina V Mashevskaya², Yurii V Shklyaev¹, Andrey N Maslivets²

Affiliations

¹ Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm 614013, Russian Federation.
² Department of Organic Chemistry, Faculty of Chemistry, Perm State University, Perm 614990, Russian Federation.

Abstract

There has been developed an easy synthetic approach to spiro[dihydrofuran-2,3'-oxindoles] via a highly diastereoselective formal [4 + 1] cycloaddition reaction of [e]-fused 1H-pyrrole-2,3-diones with diazooxindoles. The described novel heterocyclic systems are heteroanalogues of antimicrobial and antibiofilm fungal metabolites. The developed reaction represents the first example of involving 1H-pyrrole-2,3-diones fused at the [e]-side in a [4 + 1] annulation reaction.

Keywords: 1H-pyrrole-2,3-diones; [4 + 1] annulation; catalyst-free; diazooxindole; spirooxindole.

Grants and funding

This work was supported by the Perm Research and Educational Center “Rational subsoil use” (2022), X-ray diffraction and spectral analyses were performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (FSNF-2020-0008).