Synthesis of nitrogen heterocycle-fused 1,2,4-benzothiadiazine-1,1-dioxide, quinazolinone, and pyrrolidinone derivatives with a guanidine joint via sequential aza-Wittig reaction/intramolecular NH-addition cyclization/nucleophilic substitution ring closure methodology, using functionalyzed carbodiimides as key intermediates |
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Authors: | Shinsuke Hirota Nobuhide Kitamura Noriki Kutsumura Takao Saito |
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Institution: | a Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan b Functional Elemento-Organic Chemistry Unit, Advanced Science Institute, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan |
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Abstract: | We achieved efficient synthesis of imidazo- and pyrimido1,2-b]benzo-1,2,4-thiadiazine-1,1-dioxides by the tandem aza-Wittig reaction/intramolecular NH-nucleophilic addition/NH-nucleophilic substitution cyclization methodology, involving sulfonamide ester-containing carbodiimides as the key intermediates. Similarly, imidazo2,1-b]quinazolinones, imidazo1,2-a]pyrimidinediones, and imidazo1,2-a]imidazolidinediones were also synthesized through the aza-Wittig reaction-tandem cyclization strategy. When homochiral (l)-alanine methyl ester was incorporated as a building block into the corresponding iminophosphorane starting materials, we obtained optically active imidazo1,2-b]benzo-1,2,4-thiadiazine and imidazo2,1-b]quinazolinone derivatives without any racemization through the one-pot tandem methodology. |
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