Premium
On the behavior of α‐brominated dimethyl o ‐benzenediacetate toward nitrogen nucleophiles. Part II. Reaction of dimethyl α‐bromo‐ o ‐benzenediacetate with hydrazines
Author(s) -
Cignarella G.,
Cerri R.,
Savelli F.,
Maselli A.
Publication year - 1977
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.5570140322
Subject(s) - chemistry , methylhydrazine , phenylhydrazine , nucleophile , alkylation , hydrazine (antidepressant) , medicinal chemistry , bromine , derivative (finance) , nitrogen atom , nitrogen , organic chemistry , ring (chemistry) , catalysis , chromatography , financial economics , economics
Dimethyl α‐bromo‐ o ‐benzenediacetate ( 1 ) condensed with hydrazine and acetylhydrazine to give respectively 1‐carbomethoxy‐2‐amino‐1,4‐dihydro‐3‐(2 H )isoquinolinone (2) and its N ‐acetyl derivative ( 9 ). Replacement of the bromine atom of 1 with the N ‐1‐methylhydrazino ( 3 ) and the N ‐1‐phenylhydrazino ( 5 ) groups occurred by allowing 1 to react respectively with methylhydrazine and phenylhydrazine. In the latter case alkylation by 1 at the N ‐2 also occurred which led to the formation of the 2‐phenylaminoisoquinolinone ( 8 ). Derivatives 3 and 5 smoothly cyclized to the 1‐earbomethoxy‐5( H )‐1,2,3,4‐tetrahydro‐2,3‐benzodiazepin‐4‐ones 4 and 6 . A series of derivatives of 2 were also pharmacologically tested as antiinflammatory and CNS depressant agents.