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Dibenzo[ b,f ]oxepin‐10(11 H )‐one and dibenzo[ b,f ]thiepin‐10(11 H )‐one as useful synthons in the synthesis of various dibenzo[ e,h ]azulenes
Author(s) -
Pešić Dijana,
Landek Ivana Ozimec,
Rupčić Renata,
Modrić Marina,
Džapo [] Iva,
Trojko [] Rudolf,
Merćep [] Mladen,
Mesić Milan
Publication year - 2012
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.753
Subject(s) - synthon , chemistry , oxazole , thiazole , annulation , thiophene , pyrrole , azulene , furan , pyrazole , stereochemistry , imidazole , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
The present review focuses on dibenzo[ b,f ]oxepin‐10(11 H )‐one ( I , X = O) and dibenzo[ b,f ]thiepin‐10(11 H )‐one ( I , X = S) as common synthons in the efficient synthesis of various dibenzoxepino[4,5‐ and dibenzothiepino[4,5]‐fused five‐membered heterocycles: [2,3] fused thiophene ( II ), [3,4] fused thiophene ( III ), furan ( IV ), pyrrole ( V ), imidazole ( VI ), pyrazole ( VII ), oxazole ( VIII ), and thiazole ( IX ). The potential of I to be converted into reactive intermediates that readily undergo heteroaromatic annulation reactions by cyclocondensation with proper binucleophiles allows formation of a range of enumerated functionalized dibenzo[ e,h ]azulene [4] structures ( II , III , IV , V , VI , VII , VIII , IX ). Dibenzo[ e,h ]azulenes as heterotetracyclic scaffold can be exploited in further modifications to obtain compounds with altered physicochemical and biological profile. J. Heterocyclic Chem., (2012).