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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Letter Article

Sulfolane Mediated Highly Selective Synthesis of Mono and Bis-aryl-2-Methyl-6- Fluoro-Indoles and Their Halogenated Synthons

Author(s): Koppada Masthan Raju, Ravi Kumar Cheedarala* and Arumugam Pandurangan*

Volume 24, Issue 19, 2020

Page: [2283 - 2291] Pages: 9

DOI: 10.2174/1385272824999200914111909

Price: $65

Abstract

A simple, efficient, and cheap strategy has been developed for N-arylation of indoles with hexafloro benzene (1) via incorporating sulfolane as an eco-friendly solvent. NMonopentafluoroarylindole (3) at ambient conditions and N, N-bistetrafluoroaryl indole (4) at elevated temperatures were conveniently obtained by simple nucleophilic substitution using NaOH as the base and sulfolane as a reaction medium to obtain in moderately good yields, respectively. Subsequently, 3-chloro, 3-bromo, and 3-iodomono-pentafluoroarylindoles and 3, 3’-dichloro, 3, 3’-dibromo and 3, 3’-diIodobistetrafluoroaryl indoles were prepared in good yields by using respective halogenating reagents and solvents. All the chemical transformations were confirmed by analytical tools such as 1HNMR, FR-IR and HRMS analysis.

Keywords: 2-Methyl-6-fluoro-indole, hexafluorobezene, indole derivative, mono fluoroaryl indoles and bisfluoroaryl indoles, nucleophilic substitution, 1HNMR.

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