MODIFICATION OF HYDROXYBENZOPYRANOIDS - FACILE DEOXYGENATION OF 2,2-DIMETHYL-7-HYDROXY-4-CHROMANONES AND A NEW APPROACH TO THEIR NOVEL MERCAPTO ANALOGS

被引:24
作者
SEBOK, P
TIMAR, T
ESZENYI, T
PATONAY, T
机构
[1] ALKALOIDA CHEM CO LTD,DEPT CHEM RES,H-4440 TISZAVASVARI,HUNGARY
[2] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY
关键词
D O I
10.1021/jo00100a038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile deoxygenation of a systematic series of substituted 2,2-dimethyl-7-hydroxy-4-chromanones via their sulfonate, isourea, and thiocarbamate derivatives is reported. The synthesis of novel 2,2-dimethyl-7-mercapto-4-chromanones has been accomplished by the hydrolysis of the corresponding thiocarbamates. The scope and limitations of different deoxygenation procedures in the case of these hydroxybenzopyranoids are also presented.
引用
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页码:6318 / 6321
页数:4
相关论文
共 40 条
[1]   CONDENSATION PRODUCTS OF PHENOLS AND KETONES .10. THE STRUCTURE OF DIANIN COMPOUND, A UNIQUE INCLUSION-FORMING SUBSTANCE [J].
BAKER, W ;
FLOYD, AJ ;
MCOMIE, JFW ;
POPE, G ;
WEAVING, AS ;
WILD, JH .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUL) :2010-2017
[2]  
Bowers W. S., 1985, COMPREHENSIVE INSECT, V8, P551
[3]   THE EFFECT OF 2,2-DIMETHYLCHROMENE DERIVATIVES AND SOME OTHER COMPOUNDS ON THE DEVELOPMENT OF ONCOPELTUS-FASCIATUS (DALLAS) AND LOCUSTA-MIGRATORIA-MIGRATORIOIDES (R+F) [J].
BROOKS, GT ;
OTTRIDGE, AP ;
JENNINGS, RC ;
MACE, DW ;
ALEXANDER, BA .
PESTICIDE SCIENCE, 1985, 16 (06) :571-588
[4]  
CARDANI C, 1953, GAZZ CHIM ITAL, V83, P62
[5]  
COLOGNE J, 1953, B SOC CHIM FR, P573
[6]  
DRAGOTA I, 1976, REV ROUM CHIM, V21, P1543
[7]  
Ellis G.P., 1977, CHROMENES CHROMANONE
[8]  
FINDEISEN K, 1976, HOUBEN WEYL, V6, P1129
[9]  
FODOR A, 1988, J GEN COMP ENDOCRINO, V74, P18
[10]   SYNTHESIS OF BETA-TUBANOL (SYNTHESIS OF ROTENOIDS IV) [J].
FUKAMI, H ;
NAKAJIMA, M .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1961, 25 (03) :247-&