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Molecules 2006, 11(8), 583-588; doi:10.3390/11080583
Communication

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

1,* , 2 and 1,*
1 Departamento de Química Orgánica, Universidad de Valencia, 46100-Burjassot, Valencia (Spain) 2 Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain)
* Authors to whom correspondence should be addressed.
Received: 9 June 2006 / Revised: 31 July 2006 / Accepted: 1 August 2006 / Published: 9 August 2006
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Abstract

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.
Keywords: N-Nitrosoamidines; 1; 4-benzodiazepines; midazolam; alprazolam; triazolam N-Nitrosoamidines; 1; 4-benzodiazepines; midazolam; alprazolam; triazolam
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Fustero, S.; González, J.; Del Pozo, C. 1,4-Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines. Molecules 2006, 11, 583-588.

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