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Studies on quinones. XIII. Synthesis and reactivity in acid medium of cyclic O,N ‐ketals derived from acylbenzoquinones and enamines
Author(s) -
Cassis RaÚL,
Tapia Ricardo,
Valderrama Jaime A.
Publication year - 1984
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.5570210346
Subject(s) - chemistry , furan , reactivity (psychology) , ring (chemistry) , sulfuric acid , substrate (aquarium) , organic chemistry , medicinal chemistry , medicine , oceanography , alternative medicine , pathology , geology
A series of cyclic O,N ‐ketals 14–20 derived from benzo[ b ]furan has been synthesized by reaction of acylbenzoquinones and enamines. Compounds 14–20 , in warm aqueous sulfuric acid, react to give elimination or rearrangement products depending on the structure of the substrate. The behavior of heterocycles 14–20 in acid conditions is interpreted on the basis of the arrangement of the carbon substituents on the furan ring.