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Synthesis and anti‐inflammatory activity of 8 H ‐1‐thia‐8‐aza‐dibenzo[ e , h ]azulenes
Author(s) -
Ozimec Landek Ivana,
Pešić Dijana,
Merćep Mladen,
Stanić Barbara,
Mesić Milan
Publication year - 2011
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.605
Subject(s) - chemistry , azepine , substituent , epoxide , stereochemistry , ring (chemistry) , aldehyde , thiophene , lewis acids and bases , medicinal chemistry , organic chemistry , catalysis
Synthesis of a novel class of fused heterotetracyclic compounds, 8 H ‐1‐thia‐8‐aza‐dibenzo[ e , h ]azulenes ( VII ), is described. Starting N ‐benzoyl‐protected 5 H ‐dibenzo[ b , f ]azepine ( XI , PG = Bz) was oxidized to 5‐benzoyl‐10,11‐epoxy‐10,11‐dihydro‐5 H ‐dibenzo[ b , f ]azepine ( 2 ), which subsequently rearranged in Lewis acid‐induced epoxide ring opening to give 5‐benzoyl‐5,11‐dihydro‐10 H ‐dibenzo[ b , f ]azepin‐10‐one ( 3 ). Vilsmeier reaction of 3 provided β‐chlorovinyl aldehyde 4 that readily cyclized with ethyl 2‐mercaptoacetate to form dibenzazepino[4,5]‐fused thiophene structure 5 . Further transformation of substituent at C‐2 position of 5 and N ‐deprotection led to final aminoalkoxy derivatives 9 . All compounds with tetracyclic skeleton were tested in vitro for their anti‐inflammatory activity. J. Heterocyclic Chem., (2011).