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A convenient synthesis of novel pyridazino[3,4‐ b ]quinoxaline and pyrazolo[3,4‐ b ]quinoxaline utilizing 1,3‐dipolar cycloaddition reaction
Author(s) -
Kim Ho Sik,
Kurasawa Yoshihisa,
Takada Atsushi
Publication year - 1989
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.5570260550
Subject(s) - quinoxaline , chemistry , cycloaddition , dimethyl acetylenedicarboxylate , 1,3 dipolar cycloaddition , medicinal chemistry , hydrochloride , methylhydrazine , stereochemistry , organic chemistry , catalysis , phenylhydrazine
The reaction of 2,6‐dichloroquinoxaline 4‐oxide 4 with methylhydrazine gave 6‐chloro‐2‐(1‐methylhydrazino)quinoxaline 4‐oxide 5, whose reaction with dimethyl acetylenedicarboxylate or 2‐chloroacrylonitrile resulted in the 1,3‐dipolar cycloaddition reaction to afford 7‐chloro‐3,4‐bismethoxycarbonyl‐1‐methyl‐1,2‐dihydropyridazino[3,4‐ b ]quinoxaline 6 or 6‐chloro‐3‐hydroxymethylene‐1‐methyl‐2,3‐dihydro‐1 H ‐pyrazolo[3,4‐ b ] quinoxaline hydrochloride 7, respectively.