SYNTHESIS OF ARYL 2-(2-IMIDAZOLYL)ETHYL KETONES

被引：4

作者：

ABDELAAL, SM ^{[1
]}

KIM, JW ^{[1
]}

BAUER, L ^{[1
]}

机构：

[1] UNIV ILLINOIS,COLL PHARM,DEPT MED CHEM,CHICAGO,IL 60612

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1995年 / 32卷 / 03期

关键词：

D O I：

10.1002/jhet.5570320338

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Claisen-Schmidt condensation of 1-(triphenylmethyl)-2-imidazolecarboxald with acetophenones yielded 1-aryl-3-[1-(triphenylmethyl)-2-imidazolyl]propen-1-ones 7. Selective catalytic hydrogenation over platinum of 7 furnished 1-aryl-3-(2-imidazolyl)-1-propanones 8. An alternate synthesis of 8 started with sodium borohydride reduction of 7 to give allylic alcohols, 1-aryl-3-[1-(triphenylmethyl)-2-imidazolyl]-2-propen-1-ols 10, which were rearranged by hot aqueous sodium to 8. Acid hydrolysis of 8 provided the title compounds and triphenylmethanol.

引用

页码：903 / 906

页数：4

共 18 条

[1]

ABDELAAL SM, 1994, THESIS U ILLINOIS CH

[2]

BERNABE M, 1971, J MED CHEM, V14, P883

[3]

BIESEMANN H, 1959, CHEM BER, V92, P92

[4]

BUCHEL KH, 1972, ARZNEI-FORSCHUNG, V22, P1260

[5] HIGH-YIELDING SYNTHESES OF 4(5)-SUBSTITUTED IMIDAZOLES VIA ORGANOLITHIUM INTERMEDIATES - THE UTILITY OF SULFONAMIDE N-PROTECTION AND SILICON-CONTAINING BLOCKING GROUPS [J].

CARPENTER, AJ ;

CHADWICK, DJ .

TETRAHEDRON, 1986, 42 (08) :2351-2358

[6] CHALCONES + RELATED COMPOUNDS .9. PREPARATION + REARRANGEMENT OF SOME 1,3-DIPHENYLPROP-2-EN-1-OLS ( CHALCOLS ) [J].

DAVEY, W ;

HEARNE, JA .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (DEC) :4978-&

[7] NEW SYNTHESIS OF 2-NITROIMIDAZOLES [J].

DAVIS, DP ;

KIRK, KL ;

COHEN, LA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) :253-256

[8] 2-PHENETHYLIMIDAZOLE DERIVATIVES - SYNTHESIS AND ANTIMYCOTIC PROPERTIES [J].

GODEFROI, EF ;

GEENEN, JJH ;

VANKLINGEREN, B ;

VANWIJNGAARDEN, LJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (05) :530-533

[9] METALATION AND METAL-HALOGEN EXCHANGE-REACTIONS OF IMIDAZOLES [J].

IDDON, B .

HETEROCYCLES, 1985, 23 (02) :417-443

[10] ADDITION REACTIONS OF CONJUGATED DOUBLE BONDS .2. OCCURRENCE OF 1,4- OR 1,2-ADDITION IN REDUCTION OF SOME ARYL ALPHABETA-UNSATURATED KETONES WITH METAL HYDRIDES [J].

IQBAL, K ;

JACKSON, WR .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (05) :616-&

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