Published January 1, 2014
| Version v1
Journal article
Open
Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones
Creators
- 1. Oakland Univ, Dept Chem, Rochester, MI 48309 USA
- 2. Univ Massachusetts, Dept Chem, Boston, MA 02125 USA
- 3. Eastern Illinois Univ, Dept Chem, Charleston, IL 61920 USA
Description
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.
Files
bib-d79d2dc1-e704-41e8-9f6f-b58a179cd5b4.txt
Files
(275 Bytes)
| Name | Size | Download all |
|---|---|---|
|
md5:d3a09b33bfc52e06d33802a9fa1f98c6
|
275 Bytes | Preview Download |