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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,*
Received: 9 June 2006; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Fustero S, González J, Del Pozo C. 1,4-Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines. Molecules. 2006; 11(8):583-588.

Chicago/Turabian Style

Fustero, Santos; González, Javier; Del Pozo, Carlos. 2006. "1,4-Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines." Molecules 11, no. 8: 583-588.


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