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[1,2,4]Triazines. 4 . Regiospecific ring closure reactions involving 6‐amino‐5‐hydrazino[1,2,4]triazin‐3(2 H )‐ones and orthoesters
Author(s) -
Lovelette C. A.,
Geagan K.
Publication year - 1982
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.5570190618
Subject(s) - chemistry , ring (chemistry) , closure (psychology) , triazine , stereochemistry , aqueous solution , medicinal chemistry , organic chemistry , market economy , economics
6‐Amino‐5‐hydrazino[1,2,4]triazin‐3(2 H )‐one, 3 , was treated with a variety of orthoesters and concentrated acid forming mixtures of ring‐closed and open‐chain derivatives. These mixtures were converted in warm aqueous acid to the Mriazolo[5,1‐ d ][1,2,4]triazin‐3(2 H )‐ones, 11b, 14b , and 15b by a regiospecific ring closure at N‐4 of the [1,2,4]triazine ring and subsequent Dimroth‐like rearrangement of the initially formed s ‐triazolo[4,3‐ d ][1,2,4]triazin‐3(2 H )‐ones ( 11a, 14a, 15a ).