Synthesis of novel quinoline analogues of nimesulide: An unusual observation |
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| Authors: | Lingam Venkata Reddy Mamatha Nakka Alishetty Suman Soumen Ghosh Madeleine Helliwell Khagga Mukkanti Alok Kumar Mukherjee Sarbani Pal |
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| Institution: | 1. Center for Chemical Science and Technology, IST, JNTH University, Kukatpally, Hyderabad 500085, India;2. Department of Physics, Jadavpur University, Kolkata 700032, India;3. Department of Chemistry, University of Manchester, Manchester M13 9PL, England;4. Department of Chemistry, MNR Degree and PG College, Kukatpally, Hyderabad 500072, India |
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| 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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