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TsNBr 2 Mediated Synthesis of 2‐Acylbenzothiazoles and Quinoxalines from Aryl Methyl Ketones under Metal Free Condition
Author(s) -
Loukrakpam Dineshwori Chanu,
Phukan Prodeep
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900713
Subject(s) - aryl , chemistry , reaction conditions , condensation , condensation reaction , ketone , metal , organic chemistry , medicinal chemistry , catalysis , alkyl , physics , thermodynamics
An efficient one pot strategy has been developed for the synthesis of 2‐acylbenzothiazoles and quinoxalines from aryl methyl ketones. A variety of heterocycles of these two categories could be prepared in a two‐step sequence in excellent yields. The reaction was performed starting from aromatic ketones via an aryl gloxal intermediate which, on further condensation with 2‐aminobenzenethiol or o ‐phenylenediamine, produces the corresponding heterocyclic skeleton. Aromatic ketones are initially treated with TsNBr 2 in DMSO at 65 °C for 3 h and the crude reaction mixture was treated with 2‐aminobenzenethiol (at 80 °C) or o ‐phenylenediamine (at RT) to generate the final compound.