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The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalysts
Author(s) -
Takabatake Tohru,
Hasegawa Yumiko,
Hasegawa Minoru
Publication year - 1993
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.5570300602
Subject(s) - chemistry , quinoxaline , catalysis , molecular sieve , silica gel , ethyl acetoacetate , adsorption , organic chemistry , medicinal chemistry , polymer chemistry
The cyclocondensations of benzofuroxan 1a with carbonyl compounds were smoothly and efficiently carried out by the adsorption of the components on the surface of silica gel or a molecular sieve to form a 2,3‐disubstituted quinoxaline 1,4‐dioxide. When the reactions using a molecular sieve 3A (powder) were carried out at 90°, the actual reaction times were reduced to 0.5‐2 hours. Although Duerckheimer has reported the isolation of only the 7‐substituted quinoxaline 1,4‐dioxide when 5‐methoxybenzofuroxan 1e was allowed to react with ethyl acetoacetate 2j , it produced only the 6‐methoxy isomer as the reaction product by our method. 5‐Carboxybenzofuroxan 1f did not react with the carbonyl compound.