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Synthesis and structure elucidation of the condensation products between thiophene dicarbaldehydes and aromatic amines. Potential analgesic and anti‐inflammatory agents
Author(s) -
Benachenhou F.,
Mesli M. A.,
El Borai M.,
Hanquet B.,
Guilard R.
Publication year - 1988
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.5570250551
Subject(s) - chemistry , thiophene , yield (engineering) , aryl , condensation , medicinal chemistry , organic chemistry , stereochemistry , alkyl , materials science , physics , metallurgy , thermodynamics
Thiophene‐3,4‐dicarbaldehyde 1 reacts in the presence of 2‐mercaptoethanol to yield N ‐aryl‐5,6‐dihydro‐4‐oxo‐4 H ‐thieno[3,4‐ c ]pyrroles 2 and N ‐aryl‐4‐arylimino‐5,6‐dihydro‐4 H ‐thieno[3,4‐ c ]pyrroles 3 , while thiophene 2,3‐dicarbaldehyde 4 reacts with aromatic amines to give N ‐aryl‐5,6‐dihydro‐6‐oxo‐4 H ‐thieno[2,3‐ c ]pyrroles 5 in good yields. Labeling experiments and nmr spectral analysis give evidences for the possible reaction mechanism.