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Synthesis of trans ‐dihydrodiol derivatives of phenanthro[3,4‐ b ]‐thiophene and phenanthro[4,3‐ b ]thiophene
Author(s) -
Kumar Subodh,
Saravanan Srinivasan,
Reuben Peter,
Kumar Atul
Publication year - 2005
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.5570420714
Subject(s) - thiophene , chemistry , stereochemistry , organic chemistry
The present study describes the synthesis of phenanthro[3,4‐ b ]thiophene (3) , phenanthro[4,3‐ b ]thiophene (4) and its potential dihydrodiol metabolites, trans ‐6,7‐dihydroxy‐6,7‐dihydrophenanthro[3,4‐ b ]thiophene (5) and trans ‐8,9‐dihydroxy‐8,9‐dihydrophenanthro[3,4‐ b ]thiophene (6) , trans –6,7‐dihydroxy‐6,7‐dihydro‐phenanthro[4,3‐ b ]thiophene (7) and trans ‐8,9‐dihydroxy‐8,9‐dihydrophenanthro[4,3‐ b ]thiophene (8) from Suzuki coupled intermediates. The UV spectra of these dihydrodiols are presented. These spectra are useful tools for identifying these dihydrodiols among unknown metabolites of 1 and 2 produced in vitro or in vivo.