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Synthesis of 4,5‐dihydro‐4‐methyl‐1‐phenyl‐1,4,5‐benzotriazocine‐2,3,6(1 H ) triones
Author(s) -
Daniel John K.,
Peet Norton P.
Publication year - 1978
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.5570150814
Subject(s) - chemistry , sodium hydride , oxalyl chloride , methylhydrazine , benzoic acid , yield (engineering) , alkylation , dimethylformamide , medicinal chemistry , organic chemistry , chloride , catalysis , materials science , solvent , metallurgy , phenylhydrazine
The title compounds, 7a and its 9‐chloro analog 7b , were prepared in three steps from methyl N ‐phenylanthranilates. Thus, methyl N ‐phenylanthranilate ( 3a ) was treated with oxalyl chloride to yield 2‐[(2‐chloro‐1, 2‐dioxoethyl) phenylamino]benzoic acid methyl ester ( 4a ). Treatment of 4a with methylhydrazine gave 2‐([2‐(1‐methylhydrazino)‐1,2‐dioxoethyl]phenylamino) benzoic acid methyl ester ( 6a ), which was cyclized with sodium hydride in dimethylformamide to produce 7a . Alkylation of 7a and 7b with iodomethane afforded the respective 5‐methyl derivatives 8a and 8b . A survey of the known literature benzotriazocines is presented.