Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation-hydrazine cyclization reactions

Here, we report new methodology for synthesizing 2,3-benzodiazepines and their analogues by means of phosphate-assisted acylation reaction of 1-arylpropan-2-ones with a carboxylic acid followed by hydrazine cyclization in a one-pot two-step manner. An unprotected amino group is tolerated in this rea...

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Veröffentlicht in:	Organic & biomolecular chemistry 2018, Vol.16 (21), p.4013-4020
Hauptverfasser:	Sumita, Akinari, Lee, Jinhee, Otani, Yuko, Ohwada, Tomohiko
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation Benzene Benzodiazepines Biological activity Carboxylic acids Chemical reactions Chemical synthesis Hydrazine Hydrazines Phosphates Regioselectivity Selectivity Substitution reactions
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container_title	Organic & biomolecular chemistry
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creator	Sumita, Akinari Lee, Jinhee Otani, Yuko Ohwada, Tomohiko
description	Here, we report new methodology for synthesizing 2,3-benzodiazepines and their analogues by means of phosphate-assisted acylation reaction of 1-arylpropan-2-ones with a carboxylic acid followed by hydrazine cyclization in a one-pot two-step manner. An unprotected amino group is tolerated in this reaction. This method provides a direct access to 2,3-benzodiazepines containing aromatic 7,8-dimethoxy and 1-p-aminophenyl groups, which are generally considered important for bioactivity. The presence of 3,4-dimethoxy or 3-methoxy substitution on the benzene ring of the 1-arylpropan-2-one is important for high regioselectivity in the acylation reaction.
doi_str_mv	10.1039/c8ob00708j
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source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Acylation Benzene Benzodiazepines Biological activity Carboxylic acids Chemical reactions Chemical synthesis Hydrazine Hydrazines Phosphates Regioselectivity Selectivity Substitution reactions
title	Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation-hydrazine cyclization reactions
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