Premium
One‐pot Method for Reduction of Pyrazolo[5,1‐ c ][1,2,4]Triazine‐7‐diazonium Tetrafluoroborate to 7‐Hydrazinyl Derivatives
Author(s) -
Ivanov Sergey M.,
Shestopalov Anatoliy M.,
Mironovich Lyudmila M.,
Rodinovskaya Lyudmila A.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2874
Subject(s) - chemistry , anhydrous , tetrafluoroborate , triazine , medicinal chemistry , hydrolysis , organic chemistry , catalysis , ionic liquid
New convenient one‐pot method for reduction of hetarenediazonim tetrafluoroborates to the hetarylhydrazine derivatives was developed. Interaction of 8‐carboxyethyl‐3‐( tert ‐butyl)‐4‐oxo‐4,6‐dihydropyrazolo[5,1‐ c ][1,2,4]triazine‐7‐diazonium tetrafluoroborate with anhydrous SnCl 2 in anhydrous CF 3 CO 2 H, and further sequence of one‐pot operations led to formation of various derivatives of the unstable ethyl 3‐( tert ‐butyl)‐7‐hydrazinyl‐4‐oxo‐4,6‐dihydropyrazolo[5,1‐ c ][1,2,4]triazine‐8‐carboxylate (hydrochloride, hydrazides, hydrazones, and pyrazoles), which were isolated in high yields. The anhydrous conditions were first used with SnCl 2 and allowed to exclude hydrolysis of the ester group and formation of the by‐products.