Issue 39, 2020

Stereoselective synthesis of dispiro heterocycles by [3 + 2] cycloaddition of azomethine ylides with a thiazolo[3,2-a]indole derivative

Abstract

A green one pot three component [3 + 2] cycloaddition of a thiazolo[3,2-a]indole derivative (generated by the reaction of thieno[2,3-b]indole-2,3-dione and dimethyl acetylenedicarboxylate) with isatin derived azomethine ylides is reported here. An eco-friendly acetyl choline iodide–ethylene glycol (ACI/EG)-mediated deep eutectic solvent system was adopted for the reaction. Spiropyrrolidine oxindoles incorporating multiple stereocenters were obtained in a highly diastereoselective manner in excellent yields.

Graphical abstract: Stereoselective synthesis of dispiro heterocycles by [3 + 2] cycloaddition of azomethine ylides with a thiazolo[3,2-a]indole derivative

Supplementary files

Article information

Article type
Communication
Submitted
29 Jul 2020
Accepted
15 Sep 2020
First published
15 Sep 2020

Org. Biomol. Chem., 2020,18, 7822-7826

Stereoselective synthesis of dispiro heterocycles by [3 + 2] cycloaddition of azomethine ylides with a thiazolo[3,2-a]indole derivative

V. Sathi, N. V. Thomas and A. Deepthi, Org. Biomol. Chem., 2020, 18, 7822 DOI: 10.1039/D0OB01559H

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