THE CONVERSION OF BENZOTHIAZINES TO 2-ALKENYL ANILINES

被引：14

作者：

HARMATA, M

HERRON, BF

机构：

[1] Department of Chemistry, University of Missouri-Columbia, Columbia

来源：

TETRAHEDRON | 1991年 / 47卷 / 42期

关键词：

BENZOTHIAZINE; VINYL ANILINE; ALKENYL ANILINE; SULFOXIMINE; ELIMINATION;

D O I：

10.1016/S0040-4020(01)80999-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Upon treatment with excess potassium dimsylate in DMSO benzothiazines 1a-1j undergo an elimination of the sulfoximine functional group to give 2-alkenylsulfinanilides nonstereoselectively in good to excellent yield. These are easily converted to the corresponding anilines with ethanolic potassium hydroxide. Mechanistic studies indicate that the elimination reaction takes place via an El cb mechanism.

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页码：8855 / 8862

页数：8

相关论文

共 21 条

[1] 2 NEW OXINDOLE SYNTHESES [J].

FLEMING, I ;

LORETO, MA ;

WALLACE, IHM ;

MICHAEL, JP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (02) :349-359

[2] ORTHO FUNCTIONALIZATION OF AROMATIC-AMINES - BENZYLATION, FORMYLATION, AND VINYLATION OF ANILINES [J].

GASSMAN, PG ;

DREWES, HR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7600-7610

[3]

HARMATA M, UNPUB

[4]

HARMATA M, 1991, J ORG CHEM, V56

[5] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES - APPROACHES TO ERGOT ALKALOIDS [J].

HARRINGTON, PJ ;

HEGEDUS, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2657-2662

[6] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .2. TOTAL SYNTHESIS OF THE N-ACETYL METHYL-ESTER OF (+/-)-CLAVICIPITIC ACIDS [J].

HARRINGTON, PJ ;

HEGEDUS, LS ;

MCDANIEL, KF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4335-4338

[7]

HORINO H, 1979, TETRAHEDRON LETT, V20, P2403

[8] SYNTHESIS AND BIOLOGICAL EVALUATION OF 2-STYRYLQUINAZOLIN-4(3H)-ONES, A NEW CLASS OF ANTIMITOTIC ANTICANCER AGENTS WHICH INHIBIT TUBULIN POLYMERIZATION [J].

JIANG, JB ;

HESSON, DP ;

DUSAK, BA ;

DEXTER, DL ;

KANG, GJ ;

HAMEL, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1721-1728

[9]

Johnson C.R., 1985, ALDRICHIM ACTA, V18, P3

[10]

JOHNSON CR, 1979, COMPREHENSIVE ORGANI, V3, pCH11