Synthesis of 6,7-dihydro-5H-benzo[c]-1,2,4-triazolo[3,4-a]azepines and 6,7-dihydro-5H-benzo[c]tetrazolo[5,1-a]azepines

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 58; no. 12; pp. 727 - 731
• Main Authors: Glushkov, Vladimir A., Mosheva, Kseniya A., Zaitsev, Mark M., Pelykh, Vera S., Karasik, Valeriya I., Andreev, Alexander I., Dmitriev, Maksim V.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-12-2022; Springer; Springer Nature B.V
• Subjects: Acetic acid; Chemistry; Chemistry and Materials Science; Organic Chemistry; Pharmacy; Resveratrol; azepines; benzo; tetrazolo[5,1; 1,2,4-triazolobenzo[3,4; hetarylhydrazines
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-023-03149-3

Cyclization of 1-hydrazinyl-3,3-dimethyl-3,4-tetrahydro-5
H
-benzo[
c
]azepine with ethyl orthoformate gave 5,5-dimethyl-6,7-dihydro-5
H
benzo[
c
]-1,2,4-triazolo[3,4-
a
]azepine, and its reaction with acetic acid afforded 3,5,5-trimethyl-9,10-dimethoxy-6,7-dihydro-5
Н
-benzo[
c
]-1,2,4-triazolo[3,4-
a
]azepine. Nitrosation of 1-hydrazino-3,3-dimethyl-3,4-tetrahydro-5
H
-benzo[
c
]azepine led to the formation of substituted 6,7-dihydro-5
H
-benzo[
c
]tetrazolo[5,1-
a
]azepines.