1,4-Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines

Molecules

Santos Fustero¹  Javier González² 

[1] Departamento de Química Orgánica, Universidad de Valencia, 46100-Burjassot, Valencia (Spain).;Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain).

关键词: N-Nitrosoamidines;    1;    4-benzodiazepines;    midazolam;    alprazolam;    triazolam;   

DOI  :  10.3390/11080583

来源: mdpi

【 摘 要 】

1,4-Benzodiazepine N-nitrosoamidines have been used as scaffolds for the preparation of different tricyclic derivatives. Replacement of the N-nitrosoamidine moiety through treatment with the nucleophiles acetylhydrazine, aminoacetaldehyde dimethylacetal and 1-amino-2-propanol, followed by an acid-catalyzed cyclization step, afforded triazolo and imidazobenzodiazepines 1, 6, and 7, respectively, in good yields. When acetylhydrazine is used as a nucleophile, the overall process provides an alternative route to alprazolam (1b) and triazolam (1c), respectively.

【 授权许可】

Unknown   
© 2006 by MDPI (http://www.mdpi.org).