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Synthesis of 6‐halo‐5‐nitroquinoxalines
Author(s) -
Tian Wei,
Grivas Spiros
Publication year - 1992
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.5570290541
Subject(s) - chemistry , nitro , substituent , halogen , condensation , cleavage (geology) , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , physics , geotechnical engineering , fracture (geology) , engineering , thermodynamics
The 5‐nitro derivatives of 6‐haloquinoxalines have been efficiently synthesized by condensation of α‐dicarbonyls with 4‐bromo‐ or 4‐chloro‐3‐nitro‐1,2‐benzenediamines. The novel diamines were readily obtained by reductive cleavage of 5‐bromo‐ and 5‐chloro‐4‐nitro‐2,1,3‐benzoselenadiazoles. As demonstrated by the synthesis of an imidazo‐, a selenadiazolo‐ and a pyrazinoquinoxaline, the reactive halogen atom ortho to the nitro substituent renders the novel quinoxalines versatile intermediates to further heterocycles.