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

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 glyc...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-10, Vol.18 (39), p.7822-7826
Main Authors: Sathi, Vidya, Thomas, Noble V, Deepthi, Ani
Format: Article
Language:English
Subjects:
Choline
Crystallography
Cycloaddition
Ethylene glycol
Indoles
Iodides
Stereoselectivity
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Summary: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. Green synthesis of dispiro oxindole heterocycles by 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with a dipolarophile derived from thieno[2,3- b ]indole-2,3-dione.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01559h