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Synthesis of Novel Bromo‐substituted Flavone‐like Troponoid Compounds from Oxidation Cyclization of 3‐Cinnamoyl‐5,7‐dibromotropolones Using I 2 /DMSO/H 2 SO 4 System
Author(s) -
Li Yang,
Chang Mingqin,
Sun Mingchun,
Li Wei,
Gao Wentao
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990348
Subject(s) - chemistry , pyran , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry
A convenient method to obtain a series of bromo‐substituted flavone‐like troponoid compounds 6,8‐dibromo‐2‐arylcyclohepta[ b ]pyran‐4,9‐diones 3a–3s by oxidation cyclization of the readily available intermediates 3‐cinnamoyl‐5,7‐dibromotropolones 2a–2s using I 2 /DMSO/H 2 SO 4 system was realized. Compounds 2a–2s were obtained from the aldol reaction of 3‐acetyl‐5,7‐dibromotropolone 1 with various benzaldehydes. Compounds 2a–2s and 3a–3s are novel and their structures were supported by IR, 1 H NMR, MS and elemental analyses.