Iodine and ammonium persulfate mediated activation of DMSO: an approach to N-formylation of amides and synthesis of isatins

An efficient strategy towards N-formylation of amides and oxidation of indolines to isatins is described. This method employs readily available (NH4)(2)S2O8, I-2, and DMSO. The given method features operational simplicity, excellent functional group tolerance, broad substrate scope, and fast kinetic...

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Published inOrganic & biomolecular chemistry Vol. 20; no. 42; pp. 8197 - 8202
Main Authors Bhat, Showkat Ahmad, Bhat, Mohammad Yaqoob, Rather, Suhail A., Gani, Ifshana, Bhat, Khursheed Ahmad, Ahmed, Qazi Naveed
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 02.11.2022
Royal Society of Chemistry
Subjects
Amides
Ammonium
Ammonium peroxodisulfate
Chemistry
Chemistry, Organic
Functional groups
Heterocyclic compounds
Iodine
Natural products
Oxidants
Oxidation
Oxidizing agents
Physical Sciences
Science & Technology
Substrates
Synthesis
OXIDATION
REAGENT
DIMETHYL-SULFOXIDE
FACILE ACCESS
FORMAMIDES
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Summary:An efficient strategy towards N-formylation of amides and oxidation of indolines to isatins is described. This method employs readily available (NH4)(2)S2O8, I-2, and DMSO. The given method features operational simplicity, excellent functional group tolerance, broad substrate scope, and fast kinetics. Moreover, the method was applied to the synthesis of the natural product alatamide. Notably, DMSO plays three vital roles: a formyl group source, an oxidant, and a solvent.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01599d