Synthesis of (7S)-(−)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2H-1,4-diazepin-2-ones

Abstract

Synthesis of (7S)-(-)-

Divergent Regioselective Synthesis of 2,5,6,7-Tetrahydro-1H-1,4-diazepin-2-ones and 5H-1,4-Benzodiazepines

“…IR: ν max = 3440, 3338, 3223, 1744, 1726, 1624 cm À1 . MS: m/z (%) = 364 [M + ] (1), 233 (13), 202 (17), 188 (14), 173 (16), 158 (14), 144 (9), 130 (23), 121 (83), 106 (100). Anal.…”

“…The diazepinone ring is reported in the literature to be prepared from linear precursors by intramolecular reductive amination, ,− lactam formation, − and transamidation . Also, the preparation of 1,4-diazepin-2-ones involves iminophosphorane intermediates by means of intramolecular aza-Wittig reaction or hydrolysis of the iminophosphoranes to the corresponding amino derivatives followed by intramolecular cyclocondensation . The limit of these procedures is that they involve some preparative difficulties and require several steps.…”

“…22 Also, the preparation of 1,4-diazepin-2-ones involves iminophosphorane intermediates by means of intramolecular aza-Wittig reaction or hydrolysis of the iminophosphoranes to the corresponding amino derivatives followed by intramolecular cyclocondensation. 23 The limit of these procedures is that they involve some preparative difficulties and require several steps. 1,2-Diaza-1,3-dienes 24 (DDs) are versatile intermediates and react with a wide range of nucleophiles at its highly electrophilic center (at C-4), 25 leading to a wide variety of heterocyclic rings.…”