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Synthesis of 2‐formyl‐1‐aza‐dibenzo[ e , h ]azulenes
Author(s) -
Pešić Dijana,
Landek Ivana Ozimec,
Čikoš Ana,
Metelko Biserka,
Gabelica Vesna,
Stanić Barbara,
Merćep Mladen,
Mesić Milan
Publication year - 2007
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.5570440524
Subject(s) - chemistry , formylation , sodium dithionite , aldol condensation , acetaldehyde , enamine , stereochemistry , hemiaminal , medicinal chemistry , reagent , organic chemistry , ethanol , catalysis
ynthesis of a novel heterocyclic class of compounds, 1‐aza‐dibenzo[ e , h ]azulenes [1] ( 6a‐c and 7a‐c ), derived from dibenzo[ b , f ]oxepin, its 8‐chloro analogue and dibenzo[ b , f ]thiepin, respectively, is described. Aldol condensation of the starting ketones 4a‐c with (dimethyl‐hydrazono)‐acetaldehyde affords hydrazonoethylidene derivatives 5a‐c , which on reduction with sodium dithionite and subsequent cyclization provide the target tetracyclic 1‐aza‐dibenzo[ e , h ]azulenes 6a‐c . Regiospecific formylation of 6a‐c with Vilsmeier reagent leads to 2‐formyl derivatives 7a‐c . A series of derivatives 6a‐c and 7a‐c was tested for antiinflammatory activity as potential inhibitors of tumor necrosis factor alpha (TNF‐α) production in vitro .