POLYFLUOROARALKYLAMINES - AN IMPROVED SYNTHESIS OF 4,5,6,7-TETRAFLUOROINDOLE

被引：11

作者：

FILLER, R

CHEN, W

WOODS, SM

机构：

[1] Department of Chemical and Biological Sciences, Illinois Institute of Technology, Chicago

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1995年 / 73卷 / 01期

关键词：

POLYFLUOROARALKYLAMINES; SYNTHESIS; TETRAFLUOROINDOLE; NMR SPECTROSCOPY; IR SPECTROSCOPY;

D O I：

10.1016/0022-1139(94)03202-B

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Tetrafluoroindole (5), a precursor for potential biologically-active compounds, was prepared previously in a four-step synthesis from C6F6. However, catalytic reduction of pentafluorophenylacetonitrile (2) to 2-pentafluorophenylethyl amine (3) is accompanied by a significant amount of a secondary amine, which, like 3, undergoes cyclization to an indoline and subsequent dehydrogenation to a new indole 8. The side-reaction in the reduction of 2 to 3 is obviated by the use of LiAIH(4)/AlCl3 (1:1). The final aromatization to yield 5 is vastly improved by replacing MnO2 with DDQ.

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页码：95 / 100

页数：6

相关论文

共 16 条

[1] A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].

ATTENBURROW, J ;

CAMERON, AFB ;

CHAPMAN, JH ;

EVANS, RM ;

HEMS, BA ;

JANSEN, ABA ;

WALKER, T .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111

[2] PARTIALLY FLUORINATED HETEROCYCLIC COMPOUNDS .4. PREPARATION OF 4,5,6,7-TETRAFLUOROINDOLE BY A NEW CYCLISATION REACTION [J].

BROOKE, GM ;

RUTHERFO.RJ .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (13) :1189-&

[3] 4,5,6,7-TETRAFLUOROINDOLE [J].

FILLER, R ;

WOODS, SM ;

FREUDENT.AF .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (04) :811-812

[4] FLUORINE-CONTAINING CATECHOLAMINES - SYNTHESIS OF DL-2, 5, 6-TRIFLUORODOPA [J].

FILLER, R ;

RICKERT, RC .

JOURNAL OF FLUORINE CHEMISTRY, 1981, 18 (4-6) :483-495

[5] POLYFLUOROARALKYL AMINES - FURTHER-STUDIES ON THE REACTIVITY OF 4,5,6,7-TETRAFLUOROINDOLE [J].

FILLER, R ;

WOODS, SM ;

WHITE, WL .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (11) :1837-1841

[6] NEW REACTIONS OF POLYFLUOROAROMATIC COMPOUNDS . PENTAFLUOROPHENYLALANINE AND TETRAFLUOROTYROSINE [J].

FILLER, R ;

AYYANGAR, NR ;

GUSTOWSK.W ;

KANG, HH .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) :534-&

[7] POLYFLUOROAROMATICS - AN EXCURSION IN CARBANION CHEMISTRY [J].

FILLER, R .

JOURNAL OF FLUORINE CHEMISTRY, 1988, 40 (2-3) :387-405

[8]

FILLER R, 1988, ORG SYNTH COLL, V6, P873

[9] SELENIUM DIOXIDE OXIDATION OF "3-METHYL-4,5,6,7-TETRAFLUOROINDOLES - AN EFFICIENT ROUTE TO TETRAFLUORO ANALOGS OF 3-FORMYL AND 3-ACETOXYMETHYLINDOLE SYSTEMS [J].

FUJITA, M ;

OJIMA, I .

TETRAHEDRON LETTERS, 1983, 24 (42) :4573-4576

[10]

FULLER G, 1965, CHEM IND-LONDON, P651