Open Access Open Access  Restricted Access Subscription Access

THE SYNTHESIS OF 3-(HET)ARYL-6,7-DIHYDRO-5H-[1,2,4]TRIAZOLO[3,4-a][2]BENZAZEPINES

Владимир А. Глушков, Дмитрий Н. Бабенцев, Максим В. Дмитриев, Ксения А. Степанова, Анастасия Ю. Харинцева, Анастасия Е. Симахина
Cover Image

Abstract


4-Aryl-2-methylbutan-2-ols with methoxy or methylenedioxy substituents participate in the Graf–Ritter reaction with methyl thiocyanate in the presence of an acid (H2SO4, MeSO3H) forming 1-methylsulfanyl-2-benzazepines in low yields (11–35%), which undergo cyclization with benzhydrazide or hetarenecarboxylic acid hydrazides upon reflux in o-dichlorobenzene into the corresponding 3-phenyl- and 3-hetaryl-6,7-dihydro-5H-1,2,4-triazolo[3,4-a][2]benzazepines (45–74% yields).

Keywords


4-aryl-2-methylbutan-2-ols; benz[c]azepines; hetarenecarboxylic acid hydrazides; methyl thiocyanate; 1,2,4-triazolo-2-benzazepines; Ritter reaction.

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv