- Cyclometallated derivatives of palladium(II) with 1,4-benzodiazepin-2-ones. Crystal structure of (L-H)Pd(PPh3)ClCHCl3 (L = Prazepam: 7-chloro-1-cyclopropylmethyl-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one). Synthesis of isoindolobenzodiazepine derivatives by ...
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The dimeric cyclometallated derivatives of palladium(II) 2, 3 (L = 1, Diazepam: 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one) and 4 (L = 2, Prazepam: 7-chloro-1-cyclopropylmethyl-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one) react with triphenylphosphine to give the complexes (L-H)Pd(PPh3)Cl, 5 (L = Diazepam) and 6 (L = Prazepam).The crystal structure of 6 was determined by X-ray crystallography.The palladium atom is in a square planar arrangement.The deprotonated ligand is bound to the metal through the 4-nitrogen and the ortho-carbon atom of the 5-phenyl substituent.The phosphorous and the chlorine atoms are trans to the nitrogen and the carbon atoms, respectively: Pd-N = 2.085(2), Pd-P = 2.263(1), Pd-Cl = 2.377(1), Pd-C = 2.009(3) Angstroem.The reaction of the dimeric derivatives 2 with carbon monoxide was investigated.Under mild conditions (1 atm of CO, room temperature) the unstable (L-H)Pd(CO)Cl derivatives, 7 (L = Diazepam) and 8 (L = Prazepam) are formed, but at high pressure and temperature (60-100 atm of CO, 45-50 deg C), extrusion of palladium occurs and tetracyclic derivatives having an isoindolo ring condensed on the 1,4-benzodiazepin-2-one system, 9-12, are obtained.
- Cinellu, Maria Agostina,Gladiali, Serafino,Minghetti, Giovanni,Stoccoro, Sergio,Demartin, Francesco
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p. 371 - 384
(2007/10/02)
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- Process for the preparation of 1,4-benzodiazepine derivatives
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A 1,4-benzodiazepine derivative, or a pharmaceutically acceptable acid salt thereof, of the formula, SPC1 Wherein R1 is hydrogen, halogen, nitro or trifluoromethyl; R2 and R3 are independently hydrogen, halogen, lower alkyl or trifluoromethyl; R4 is lower alkyl, alkenyl, trihaloalkyl, alkoxyalkyl, alkenyloxyalkyl, alkoxyalkoxyalkyl, alkanoyloxyalkyl, cycloalkylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or a group of the formula EQU1 in which R6 and R7 are independently lower alkyl, and n is an integer of 1 to 4; and R5 is hydrogen or lower alkyl, is obtained by reacting a benzophenone derivative of the formula, SPC2 Wherein R1, R2, R3 and R4 are as defined above, with a 2-isocyanatoacetyl chloride derivative of the formula EQU2 wherein R5 is as defined above.
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