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Studies on quinones. VII . Synthesis of some benzo[ b ]thiophene‐4,7‐diones
Author(s) -
Ruiz V. M.,
Tapia R.,
Valderrama J.,
Vega J. C.
Publication year - 1981
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.5570180620
Subject(s) - chemistry , thiophene , carboxylate , ether , medicinal chemistry , stereochemistry , organic chemistry
The synthesis of methyl 4,7‐dihydro‐4,7‐dioxobenzo[ b ]thiophene‐2‐carboxylate ( 20 ) based on the reaction of methyl mercaptoacetate with activated 1,4‐benzoquinones is described. Methyl 4,7‐dihydro‐4,7‐dioxo‐5‐hydroxybenzo[ b ]thiophene‐2‐carboxylate ( 24 ) and its corresponding methyl ether 26 were obtained through a Thiele‐Winter acetoxylation on 20 . On the basis of the properties of methyl 4,7‐dihydro‐4,7‐dioxo‐6‐methoxy‐benzo[ b ]thiophene‐2‐carboxylate ( 21 ) obtained from 2,4,5‐trimethoxybenzaldehyde ( 32 ), the structures of the products 24 and 26 are proposed.