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A selective synthesis of 2‐arylamino‐4 H ‐1,3,4‐thiadiazino[5,6‐ b ]‐quinoxalines and mesoionic triazolo[4,3‐ a ]quinoxaline
Author(s) -
Kim Ho Sik,
Kim Tong Eun,
Kwag Sam Tag,
Park Yong Tae,
Hong Young Seuk,
Okamoto Yoshihisa,
Kurasawa Yoshihisa
Publication year - 1997
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.5570340525
Subject(s) - quinoxaline , chemistry , mesoionic , triethylamine , trifluoroacetic anhydride , medicinal chemistry , hydrolysis , organic chemistry
The reaction of the 6‐chloro‐2‐(1‐methyl‐2‐thiocarbamoylhydrazino)quinoxaline 4‐oxides 3a‐d with trifluoroacetic anhydride gave the 2‐( N ‐aryl)trifluoroacetamido‐8‐chloro‐4‐methyl‐4 H ‐1,3,4‐thiadiazino‐[5,6‐ b ]quinoxalines 7a‐d , respectively, while the reflux of compounds 3a‐c in N,N ‐dimethylformamide afforded the mesoionic triazolo[4,3‐ a ]quinoxaline 4 . Hydrolysis of compounds 7a‐d with triethylamine/water provided the 2‐arylamino‐8‐chloro‐4‐methyl‐4 H ‐1,3,4‐thiadiazino[5,6‐ b )]quinoxalines 8a‐d , respectively.