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Synthesis of 8‐substituted naphtho[2,1‐ b ]thiophenes with cationic side chains at position 4
Author(s) -
Kusuma Srihari,
Wilson W. David,
Boykin David W.
Publication year - 1985
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.5570220518
Subject(s) - thiophene , chemistry , cationic polymerization , amide , side chain , medicinal chemistry , stereochemistry , organic chemistry , polymer
A series of five 8‐substituted α‐[bis(2‐hydroxyethyi)aminoethyl]naphtho[2,1‐ b ]thiophenes 7 and a series of seven N ‐(3‐dimethylaminopropyl)‐8‐substituted naphtho[2,1‐ b ]thiophene‐4‐carboxamides 8 have been synthesized. The naphtho[2,1‐ b ]thiophene‐4‐carboxylic acids 4 were prepared by photooxidative cyclization of α‐(2‐thienyi)‐β‐arylacrylic acids 3. The carboxylic acids 4 were converted by a conventional five step route involving α‐bromoketone intermediates to the a‐[bis(2‐hydroxyethyl)aminomethyl]‐8‐substituted naphtho‐[2,1‐6]thiophene‐4‐methanols 7 and by a standard two‐step amide preparation to the N ‐(3‐dimethylaminopropyl)‐8‐substituted naphtho[2,1‐6]thiophene‐4‐carboxamides 8 .