Synthesis of Some New 2‐Oxo‐N‐[(10H‐phenothiazin‐10‐yl)alkyl] Derivatives of Azetidine‐1‐carboxamides |
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| Authors: | Ritu Sharma Pushkal Samadhiya S D Srivastava S K Srivastava |
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| Institution: | 1. Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H.?S. Gour University , (A Central University);2. Sagar‐470003, India, (phone: +91‐9907656136) |
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| Abstract: | The synthesis of a new series of 4‐aryl‐3‐chloro‐2‐oxo‐N‐3‐(10H‐phenothiazin‐10‐yl)propyl]azetidine‐1‐carboxamides, 4a – 4m , is described. Phenothiazine on reaction with Cl(CH2)3Br at room temperature gave 10‐(3‐chloropropyl)‐10H‐phenothiazine ( 1 ), and the latter reacted with urea to yield 1‐3‐(10H‐phenothiazin‐10‐yl)propyl]urea ( 2 ). Further reaction of 2 with several substituted aromatic aldehydes led to N‐(arylmethylidene)‐N′‐3‐(phenothiazin‐10‐yl)propyl]ureas 3a – 3m , which, on treatment with ClCH2COCl in the presence of Et3N, furnished the desired racemic trans‐2‐oxoazetidin‐1‐carboxamide derivatives 4a – 4m . The structures of all new compounds were confirmed by IR, and 1H‐ and 13C‐NMR spectroscopy, FAB mass spectrometry, and chemical methods. |
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| Keywords: | Azetidin‐2‐ones Phenothiazine |
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