The Synthesis and Chemistry of Azolobenzodiazepines

Prescribed drugs containing nitrogen heterocycles: an overview

“…[251][252][253] It is most frequently taken orally for the short term controlling of anxiety disorders, specially panic disorder or general anxiety disorder (GAD). 254 Alprazolam, is actually 8- 255 The similar strategy that is employed to prepare triazolam can be applied to synthesis alprazolam, with the exclusion which it starts from 2-amino-5-chlorobenzophenone as starting material. [256][257][258] Worthy to notice a non-typical approach for the synthesis of alprazolam starting from 2,6-…”

“…254 Alprazolam, is actually 8-chloro-1-methyl-6-phenyl-4 H-s -triazolo[4,3- a ][1,4]benzodiazepine 193. 255 The similar strategy that is employed to prepare triazolam can be applied to synthesis alprazolam, with the exclusion which it starts from 2-amino-5-chlorobenzophenone as starting material. 256–258 Worthy to notice a non-typical approach for the synthesis of alprazolam starting from 2,6-dichloro-4-phenylquinoline, has also been proposed.…”

“…Buspirone 489 is an extremely specific drug that could possibly represent a new chemical class of anxiolytics-azaspirones but has not been found to be effective in treating psychosis. 255 Buspirone, 8-[4-[4-(2-pyrimidyl)-1-piperazinyl]butyl]-8-azaspiro[4,5]decan-7,9-dione 489, was synthesized started with 1-(2-pyrimidyl)piperazine 484 which reacted with 4-chlorobutyronitrile 485, to afford 4-(2-pyrimidyl)-1-(3-cyanopropyl)piperazine 486. The latter was hydrogenated in the presence of RANEY® to give, 1-(2-pyrimidyl)-4-(4-aminobutyl)piperazine 487 which upon reaction with 8-oxaspiro[4,5]decan-7,9-dione 488 afforded the desired compound, buspirone 489 ( Scheme 69 ).…”

Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold—A Useful Tool for Bioactive Molecules Design

“…Its further development is largely dependent on the availability of new synthetic methods and approaches leading to heterocyclic derivatives [ 1 ]. Tricyclic heterocyclic scaffolds, possessing two non-polar phenyl rings separated by a seven-membered heterocycle, and their structural analogues, are challenging synthetic targets for organic chemists [ 2 , 3 , 4 , 5 ]. The development of a wide range of novel synthetic methods has led to the synthesis of a broad variety of derivatives with significant biological activity, where the tricyclic antipsychotic drugs focused the most attention [ 6 ].…”

“…A brief literature survey revealed, that such compounds could be obtained from a condensation reaction of benzene-1,2-diamine and diethyl phthalate [13], benzene-1,2-diamine, and benzocyclobutene-l,2-dione [14,15] or Beckmann rearrangement of appropriate tricyclic dibenzoazepine oximes [16,17]. The parent compound 3 (R 1 = R 2 = R 3 = R 4 = H) could also be synthesized from benzene-1,2-diamine and 1,2-phenylenebis ((1H-benzo[d] [1,2,3]triazol-1-yl)methanone) obtained from phthaloyl dichloride and 1H-benzo [d] [1,2,3]triazole [18], while condensation of 5,6-diaminouracil with phtalic anhydride resulted in the formation of fused pyrimido [4,5-b] [1,4]diazocine ring [19].…”