1449653-75-1Relevant academic research and scientific papers
Synthesis of N-acylated 1,5-benzodiazepines: Differentiation between two possible acylation sites via hydrogen bonding
Escobar, Carlos A.,Alvarado, Odette A.,Howard, Judith A.K.,Fuentealba, Mauricio
, p. 397 - 402 (2013)
Temperature-dependent regioselectivity between amino and hydroxyl groups mediated by hydrogen bonding was observed in the reaction of acetic anhydride with 2-(2,3-dimethoxyphenyl)- 4-(2-hydroxyphenyl)-2,3-dihydro-1H-1,5- benzodiazepine (1), obtaining 1-acetyl-2-(2,3-dimethoxyphenyl)-4-(2- hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine (1a), when these were reacted at room temperature, and 4-(2-acetoxyphenyl)-1-acetyl-2-(2,3-dimethoxyphenyl)-2, 3-dihydro-1H-1,5-benzodiazepine (1b), when they were refluxed (148 - 150 °C). Acylation of the less hindered analog 4-(2-hydroxyphenyl)-2-phenyl-2,3- dihydro-1H-1,5-benzodiazepine (2) via crotonyl chloride (a bulky acylating agent compared with acetic anhydride) afforded by refluxing only 1-crotonyl-4- (2-hydroxyphenyl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine (2a). All compounds were characterized spectroscopically, and the molecular structures of compounds 1a and 2a were determined by X-ray diffraction analysis.
