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Synthesis of novel quinoline analogues of nimesulide: An unusual observation

✍ Scribed by Lingam Venkata Reddy; Mamatha Nakka; Alishetty Suman; Soumen Ghosh; Madeleine Helliwell; Khagga Mukkanti; Alok Kumar Mukherjee; Sarbani Pal

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
251 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Reduction of nimesulide followed by treating the N‐acyl derivative of resulting arylamine with Vilsmeier‐Haack reagent provided novel 2‐chloro‐3‐formylquinoline derivatives. The construction of quinoline ring using Vilsmeier‐Haack reagent afforded an unexpected compound, N‐(2‐chloro‐3‐formyl‐7‐phenoxy quinolin‐6‐yl)formamide, in addition to the expected product. The structure of this unexpected quinoline derivative was established via single‐crystal X‐ray analysis and its formation could be explained by an unprecedented N‐S bond cleavage under Vilsmeier‐Haack reaction conditions. The 2‐chloro‐3‐formylquinoline derivatives obtained were converted to a number of corresponding Schiff bases with potential pharmacological importance. J. Heterocyclic Chem., 2011.

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