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Synthesis of quinoxaline derivatives through condensation of 1,2‐diaminobenzenes with β‐keto sulfoxides
Author(s) -
Kano Shinzo,
Shibuya Shiroshi,
Yuasa Yoko
Publication year - 1980
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.5570170741
Subject(s) - quinoxaline , chemistry , condensation , acetic acid , medicinal chemistry , condensation reaction , organic chemistry , catalysis , physics , thermodynamics
Abstract The reaction of o ‐phenylenediamine with α‐methylsulfinylcyclohexanone and α‐methylsulfinylcyclopentanone in the presence of acetic acid afforded 1,2,3,4‐tetrahydrophenazine and 2,3‐dihydro‐1 H ‐cyclopenta[ b ]‐quinoxaline, respectively. 3,4‐Diaminotoluene and 3,4‐diaminochlorobenzene were reacted with α‐methyl‐sulfinylacetophenone to give a mixture of the corresponding 6‐ and 7‐substituted 2‐phenylquinoxaline. Condensation of 3,4‐diaminomethoxybenzene with α‐methylsulfinylacetophenone gave 7‐methoxy‐2‐phenylacetophenone, whereas, the same reaction between 3,4‐diaminonitrobenzene and α‐methylsulfinylacetophenone yielded 6‐nitro‐2‐phenylquinoxaline.