Synthesis of novel quinoline analogues of nimesulide: An unusual observation

Autor: Lingam Venkata Reddy, Mamatha Nakka, Madeleine Helliwell, Sarbani Pal, Alishetty Suman, Soumen Ghosh, Khagga Mukkanti, Alok Kumar Mukherjee
Rok vydání: 2011
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 48:555-562
ISSN: 0022-152X
DOI: 10.1002/jhet.618
Popis: 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.
Databáze: OpenAIRE