Synthesis of Substituted 5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines
✍ Scribed by L. Kosychova; Z. Stumbreviciute; L. Pleckaitiene; R. Janciene; B. D. Puodziunaite
- Book ID
- 111577867
- Publisher
- Springer US
- Year
- 2004
- Tongue
- English
- Weight
- 188 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0009-3122
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## Abstract A series of 3a,5‐diaryl‐1,3‐diphenyl‐3a,4,5,6‐tetrahydro‐3H‐1,2,4‐triazolo[4,3‐a][1,5]benzo‐diazepines was synthesized by the cycloaddition reactions of 2,4‐diaryl‐2,3‐dihydro‐1H‐1,5‐benzo‐diazepines and N‐phenylbenzonitrileimine generated from N‐phenylbenzenecarbohydrazonic chloride in
In the title compound, C 11 H 14 N 2 O, the diazepine ring adopts a skewed boat conformation. The molecule is stabilized by N-HÁ Á ÁO intermolecular hydrogen bonds, forming a zigzag chain parallel to the b axis.
The reaction of 3-mercapto-4-aryIideneamino-l,2,4triazoles 2b-d, 3a-d with ethyl bromoacetate and/or phenacyl bromide in hot DMF and triethylamine affords the stereochemically pure 7-acyl-6-aryl-6,7dihydro-5H-lt2, 4-triazolo[3,4-b][l, 3,4]thiadiazines