1H-1,4-Benzodiazepine → 4-Phenyl-2-quinazolinecarbaldehyde

Beteiligte Stoffe

Reaktionsschritte

The conversion of benzo[e][1,4]diazepine derivatives into 4-phenyl-quinazolines, such as the refluxing of 3-hydroxy-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one in AcOH to give 35% of 4-phenyl-2-quinazolinecarbaldehyde [30], thermolysis of 7-chloro-3-(2-methylimidazol-1-yl)-5-phenyl-3H-1,4-benzodiazepin-2-amine in 50% H2SO4 that afforded about 15% of 6-chloro-4-phenyl-2-quinazolinecarbaldehyde [31], thermolysis of 7-bromo-3-hydroxy-5-pyridin-2′-yl-3H-1,4-benzodiazepin-2(1H)-one at 220° C. to give 6-bromo-4-pyridin-2′-yl-2-quinazolinecarbaldehyde [32], sublimation of 7-chloro-5-phenyl-1,3-dihydro-2,1,4-benzothiadiazepine 2,2,4-trioxide at 160° C. under vacuum (at 10−3 mmHg) to give 6-chloro-4-phenylquinazoline [33], acidic hydrolysis of 8-chloro-6-phenyl-3,4-dihydro-1,5-benzodiazocin-2-amine in refluxing methanolic hydrogen chloride for 2.5 hours to afford 53% of 2-α-aminoethyl-6-chloro-4-phenylquinazoline [34], treatment of 8-chloro-3-methyl-6-phenyl-3H-4,1,5-benzoxadiazocin-2(1H)-one with sodium methoxide for 20 hours to yield 50% of 2-acetyl-6-chloro-4-phenylquinazoline [35], oxidation of N-methyl-7-nitro-5-phenyl-1H-1,4-benzodiazepine-3-carboxamide with CrO3 in AcOH to give 29% of N-methyl-6-nitro-4-phenyl-2-quinazolinecarboxamide [36], and hydrogenation of 8-chloro-6-phenyl-3H-4,1,5-benzoxadiazocin-2(1H)-one oxime over Raney-nickel to afford 50% of 6-chloro-2-hydroxymethyl-4-phenylquinazoline [37];

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