Syntheses of side-chain fluorinated biologically important imidazoles and indoles

被引：19

作者：

Dolensky, B ^{[1
]}

Nam, G ^{[1
]}

Deng, WP ^{[1
]}

Narayanan, J ^{[1
]}

Fan, JF ^{[1
]}

Kirk, KL ^{[1
]}

机构：

[1] NIDDKD, Bioorgan Chem Lab, NIH, Dept Hlth & Human Serv, Bethesda, MD 20892 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2004年 / 125卷 / 04期

关键词：

imidazoles; indoles; biogenic amines; FBr" addition; deoxyfluorination;

D O I：

10.1016/j.jfluchem.2003.12.013

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We review in this report the preparation of several side-chain fluorinated analogues of biologically important imidazoles and indoles. The building blocks used should also have applications in other synthetic problems. The addition of "FBr" to vinyl imidazole derivatives was used to prepare beta-fluoro- and beta,beta-difluorohistamine and histidinols, as well as beta-fluorourocanic acid. Deoxyfluorination of intermediate acylindoles was used to prepare a series of beta,beta-difluorotryptamine derivative, including the fluorinated analogue of the important neurotransmitter, serotonin. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：501 / 508

页数：8

共 46 条

[1]

ALVERNHE G, 1987, SYNTHESIS-STUTTGART, P562

[2] SYNTHESIS AND REACTIONS OF SOME 3-(2-HALOACYL)INDOLES [J].

BERGMAN, J ;

BACKVALL, JE ;

LINDSTRO.JO .

TETRAHEDRON, 1973, 29 (07) :971-976

[3]

Boguslavskaya L. S., 1972, RUSS CHEM REV, V41, P740, DOI 10.1070/RC1972v041n09ABEH002089

[4]

BOGUSLAVSKAYA LS, 1984, RUSS CHEM REV, V53, P1178

[5] ELIMINATION FROM DIASTEREOISOMERIC METHYL 3-ACETOXY-2-HALOGENO-3-PHENYLPROPANOATES AND 2,3-DIHALOGENO-3-PHENYLPROPANOATES [J].

CABALEIRO, MC ;

GARAY, RO .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (10) :1473-1476

[6] MECHANISM OF IMMUNE SUPPRESSION BY ULTRAVIOLET-IRRADIATION INVIVO .1. EVIDENCE FOR THE EXISTENCE OF A UNIQUE PHOTORECEPTOR IN SKIN AND ITS ROLE IN PHOTOIMMUNOLOGY [J].

DEFABO, EC ;

NOONAN, FP .

JOURNAL OF EXPERIMENTAL MEDICINE, 1983, 158 (01) :84-98

[7] Syntheses of β,β-difluorotryptamines [J].

Deng, WP ;

Nam, G ;

Fan, JF ;

Kirk, KL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2798-2802

[8] Preparation of β-fluoro- and β,β-difluoro-histidinols [J].

Dolensky, B ;

Narayanan, J ;

Kirk, KL .

JOURNAL OF FLUORINE CHEMISTRY, 2003, 123 (01) :95-99

[9] New approaches to side-chain fluorinated bioimidazoles: 4-alkynylimidazoles as substrates for fluorination [J].

Dolensky, B ;

Kirk, KL .

JOURNAL OF FLUORINE CHEMISTRY, 2003, 124 (01) :105-110

[10] Preparation of (fluoromethyl)- and (difluoromethyl) imidazoles [J].

Dolensky, B ;

Kirk, KL .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2002, 67 (09) :1335-1344

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