Synthesis of Novel Quinoline Analogues of Nimesulide: An Unusual Observation

[摘要]：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.

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