Journal
FRONTIERS IN CHEMISTRY
Volume 11, Issue -, Pages -Publisher
FRONTIERS MEDIA SA
DOI: 10.3389/fchem.2023.1174895
Keywords
1,3-benzoazaphosphole analogues; 2-aminophenyl(phenyl)phosphine; practical synthesis route; stable phosphorus key intermediate; heterocycles
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In this study, 1,3-benzoazaphosphol analogues were successfully synthesized by establishing a fundamental technology for the introduction of phosphorus groups into aromatic rings and formation of five-membered rings containing phosphorus and nitrogen by cyclization. The key intermediate, 2-aminophenyl(phenyl)phosphine, showed high stability and easy handling. These findings provide promising synthetic routes for the development of five-membered heterocyclic compounds containing phosphorus and nitrogen.
Despite the promising pharmacological activity and material properties of five-membered heterocyclic compounds containing phosphorus and nitrogen, synthetic examples of them have been rather limited due to the instability of phosphorus toward air and water. In this study, 1,3-benzoazaphosphol analogues were selected as target molecules, and various synthetic routes were examined to establish a fundamental technology for the introduction of phosphorus groups into aromatic rings and formation of five-membered rings containing phosphorus and nitrogen by cyclization. As a result, we found that 2-aminophenyl(phenyl)phosphine is an extremely promising synthetic intermediate with high stability and easy handling. Furthermore, 2-methyl-3-phenyl-2,3-dihydro-1H-benzo[d][1,3]azaphosphole and 3-phenyl-2,3-dihydro-1H-benzo[d][1,3]azaphosphole-2-thione as synthetically useful 1,3-benzoazaphosphol analogues were successfully synthesized by using 2-aminophenyl(phenyl)phosphine as a key intermediate.
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