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Issue 3, 2014
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Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones

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Abstract

Reaction of alk-3-yn-1-ones with o-phenylenediamines provides an effective method with high atom economy for the synthesis of diversely substituted benzodiazepines and conjugated enaminones. This microwave-accelerated reaction proceeds in ethanol in the absence of a catalyst and leads to benzyl-substituted 1,5-benzodiazepines with good yields (70–92%). A room temperature protocol with the same set of reagents (stabilized with triethylamine) leads to enaminones (3-amino-2-alkenones, 70–99%). The tautomer formed and the regio- and stereochemistry of the process are confirmed by the X-ray crystallographic structure determination of 2-(4-methylbenzyl)-4-phenyl-3H-benzo[b][1,5]diazepine and (Z)-3-[(2-amino-4,5-dimethylphenyl)amino]-4-(4-tert-butylphenyl)-1-(4-chlorophenyl)but-2-en-1-one.

Graphical abstract: Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones

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Supplementary files

Article information


Submitted
10 Sep 2013
Accepted
29 Nov 2013
First published
19 Dec 2013

Green Chem., 2014,16, 1120-1124
Article type
Communication

Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones

A. Solan, B. Nişanci, M. Belcher, J. Young, C. Schäfer, K. A. Wheeler, B. Török and R. Dembinski, Green Chem., 2014, 16, 1120
DOI: 10.1039/C3GC41898G

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