Synthesis of 4,5‐dihydro‐4‐methyl‐1‐phenyl‐1,4,5‐benzotriazocine‐2,3,6(1 H ) triones | Zendy

Daniel John K. | Zendy; Peet Norton P. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research