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

Abstract

We achieved efficient synthesis of imidazo- and pyrimido[1,2-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, imidazo[2,1-b]quinazolinones, imidazo[1,2-a]pyrimidinediones, and imidazo[1,2-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 imidazo[1,2-b]benzo-1,2,4-thiadiazine and imidazo[2,1-b]quinazolinone derivatives without any racemization through the one-pot tandem methodology.