A novel molecular I2-catalyzed synthesis of isatins through C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated. This journal is © the Partner Organisations 2014.

Govindasamy Sekar

Department Of Chemistry

Selvaraj Chandrasekar

C-n bond formations

2-AMINOACETOPHENONE

acetophenone derivative

indole derivative

Iodine

Isatin

OXINDOLE

catalysis

chemistry

oxidation reduction reaction

synthesis

Acetophenones

Indoles

Oxidation-Reduction

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Organic and Biomolecular Chemistry

The metal and ligand free chemoselective reduction of the keto group and complete reduction of the both keto and amide groups of α-keto amide with hydrosilanes using tetrabutylammoniumflouride (TBAF) as catalyst have been accomplished. This methodology affords an efficient and economic route for the synthesis of biologically important α-hydroxy amides and β-amino alcohols. The other important advantage of this TBAF catalyst is chemoselective reduction of ketones to corresponding alcohols in the presence of several other sensitive functional groups. © The Royal Society of Chemistry 2014.

Fulltext

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Metal free chemoselective reduction of α-keto amides using TBAF as catalyst

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An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones

Journal	Data powered by TypesetOrganic and Biomolecular Chemistry
Publisher	Data powered by TypesetRoyal Society of Chemistry
ISSN	14770520
Open Access	No