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A new method for the synthesis of novel 1‐aryl‐3‐quinoxalinyl‐1,2,4‐triazol‐5‐ones
Author(s) -
Kurasawa Yoshihisa,
Muramatsu Muneto,
Hotehama Keizo,
Okamoto Yoshihisa,
Takada Atsushi
Publication year - 1985
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.5570220647
Subject(s) - chemistry , hydrazine (antidepressant) , curtius rearrangement , hydrate , nitrous acid , aryl , medicinal chemistry , diazonium compounds , organic chemistry , combinatorial chemistry , chromatography , alkyl
The reactions of 3‐methoxycarbonylmethylene‐2‐oxo‐1,2,3,4‐tetrahydroquinoxaline 1 with aryl diazonium salts gave 3‐(α‐aryldiazenylmethoxycarbonylmethylene)‐2‐oxo‐1,2,3,4‐tetrahydroquinoxalines 2a‐c , whose reactions with hydrazine hydrate afforded 3‐(α‐aryldiazenylhydrazinocarbonylmethylene)‐2‐oxo‐1,2,3,4‐tetrahydroquinoxalines 3a‐c . The reactions of 3a‐c with nitrous acid resulted in the Curtius rearrangement to provide the 1‐aryl‐3‐quinoxalinyl‐1,2,4‐triazol‐5‐ones 4a‐c.