An efficient proline-catalyzed synthesis of 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles has been accomplished from 1,3-dicarbonyl compounds and sulfonyl azides. The developed reaction is suitable for various symmetrical and unsymmetrical 1,3-dicarbonyl compounds, tolerates various functional groups and affords 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles in good yield with excellent regioselectivity. Rhodium-catalyzed denitrogenative functionalization of 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles further demonstrates their utility in organic synthesis. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Pazhamalai Anbarasan

Department Of Chemistry

Shanmugam Rajasekar

chemistry

Synthesis (chemical)

1 ,3-dicarbonyl compounds

Annulation

Organocatalysis

proline

Triazoles

catalysis

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

Chemistry - An Asian Journal

A General Proline-Catalyzed Synthesis of 4,5-Disubstituted N-Sulfonyl-1,2,3-Triazoles from 1,3-Dicarbonyl Compounds and Sulfonyl Azide

A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemistry - A European Journal

One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

Clinical Chemistry

OUP accepted manuscript

2019 Chinese Control And Decision Conference (CCDC)

CCDC 2019 Front Matter

Angewandte Chemie International Edition

Selective Functionalization of Aromatic C(sp2)−H Bonds in the Presence of Benzylic C(sp3)−H Bonds by Electron-Deficient Carbenoids Generated from 4-Acyl-1-Sulfonyl-1,2,3-Triazoles

Journal	Data powered by TypesetChemistry - An Asian Journal
Publisher	Data powered by TypesetJohn Wiley and Sons Ltd
ISSN	18614728
Open Access	No