Selectfluor‐Mediated N‐Methylation, N‐Methylenesulfonylmethylation and Methylenethiomethylation of Isatins in Dimethyl Sulfoxide-Reference-Cited by-同舟云学术

Selectfluor‐Mediated N‐Methylation, N‐Methylenesulfonylmethylation and Methylenethiomethylation of Isatins in Dimethyl Sulfoxide

Published:2024-05-17 Issue:19 Volume:9 Page:
ISSN:2365-6549
Container-title:ChemistrySelect
language:en
Short-container-title:ChemistrySelect

Author:

Choudhari Dnyaneshwar J.¹,Babu Nanubolu Jagadeesh²³,Rode Haridas B.¹³^ORCID

Affiliation:

1. Department of Natural Products and Medicinal Chemistry CSIR-Indian Institute of Chemical Technology Tarnaka Hyderabad-500 007 India

2. Laboratory of X-ray Crystallography CSIR-Indian Institute of Chemical Technology Tarnaka Hyderabad 500 007 India

3. Academy of Scientific and Innovative Research Ghaziabad Uttar Pradesh-201 002 India

Abstract

AbstractDimethyl sulfoxide as a reagent and solvent in Selectfluor mediated transformations of isatin is reported. The transformations include N‐methylation and N‐methylenesulfonylmethylation of isatin at 100 °C whereas N‐methylenethiomethylation was observed at 140 °C in addition to N‐methylation and N‐methylenesulfonylmethylation of isatins. Electron withdrawing and releasing substituents on isatin were tolerated. Interestingly, dual (N‐ and C−)methylenethiomethylation was observed in case of 7‐Bromo‐ and 7‐Iodo isatins at 140 °C. This protocol efficiently afforded various isatin analogs using DMSO/Selectfluor system.

Publisher

Wiley

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