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Synthesis of carbon‐14 labeled 1, 4‐benzodiazepines
Author(s) -
Hsi Richard S. P.
Publication year - 1973
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590090307
Subject(s) - hydrazide , benzodiazepine , hydrazine (antidepressant) , acetic acid , chemistry , medicinal chemistry , acetic anhydride , organic chemistry , catalysis , receptor , chromatography , biochemistry
Reaction of 7‐chloro‐1, 3‐dihydro‐5‐phenyl‐2H‐1, 4‐benzodiazepine ‐2‐thione (Ia) and 7‐chloro‐5‐(2‐chlorophenyl)‐1, 3‐dihydro‐2H, 1, 4‐benzodiazepine‐2‐thione (Ib) with hydrazine produces. respectively, 7‐chloro‐5‐phenyl‐3H‐1, 4‐benzo‐diazepin‐2‐yl hydrazin (IIa) and 7‐chloro‐5(2‐chlorphenyl)‐3H‐1, 4‐benzodiaze‐pin‐d‐ylhydrazine (IIb). Acetylation of IIa and IIb with N‐acetyl ‐ 1 14 C‐imida‐zole affords acetic acid‐1‐ 14 C 2‐(7‐chloro‐5‐phenyl‐3H‐1, 4‐benzodiazenpin‐2‐yl) hydrazide (IIIa) and acetic acid‐1‐ 14 C 2‐[7‐chloro‐5‐(2‐chlorphenyl) ‐3H‐1, 4‐benzodiazepine‐2‐yl] hydrazide (IIIb). Compounds IIIa and IIIb are thermally cyclised to give 8‐chloro‐1‐methyl‐6‐phenyl‐4H‐s‐triazol [4, 3] [1, 4] benzodiase‐pine‐1‐ 14 c (IVa) and 8‐chloro‐6 (2‐chlorophenyl)‐1‐methyl‐4H‐s‐trizolo[4, 3‐a] ‐[1, 4] benzodiazepine ‐1‐ 14 C (IVb).