NEW EVIDENCE ON THE FORMATION OF 3-ACYLINDOLES BY REACTION OF N-PHENYLNITRONES WITH ALPHA,BETA-ACETYLENIC SULFONES

被引：15

作者：

BROGGINI, G

DILIDDO, D

ZECCHI, G

机构：

[1] Dipartimento di Chimica Organica E Industrial, Milano, 20133

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 01期

关键词：

D O I：

10.1002/jhet.5570280116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Phenylnitrones react with alpha,beta-acetylenic sulfones to give ultimately 3-acylindoles via unstable 4-sulfonyl-substituted 2,3-dihydroisoxazoles. In one case, a minor pathway is also operative leading to a different kind of indole derivative. Mechanistic possibilities are discussed.

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页码：89 / 91

页数：3

相关论文

共 15 条

[1] ALKYLTHIATION AND ARYLTHIATION OF URACIL AND INDOLE [J].

ANZAI, K .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (03) :567-569

[2] FORMATION OF NITRONES AND OTHER PRODUCTS IN THE REACTION OF N-ALKYL-HYDROXYLAMINES AND N-ARYLHYDROXYLAMINES WITH VARIOUS ACETYLENE DERIVATIVES [J].

AURICH, HG ;

HAHN, K .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08) :2769-2775

[3]

BLECHERT S, 1985, LIEBIGS ANN CHEM, P673

[4]

CAPOZZI G, 1986, J CHEM RES-S, P234

[5]

DALLACROCE P, 1983, J HETEROCYCLIC CHEM, V20, P519, DOI 10.1002/jhet.5570200306

[6] DELTA-4-ISOXAZOLINES (2,3-DIHYDROISOXAZOLES) [J].

FREEMAN, JP .

CHEMICAL REVIEWS, 1983, 83 (03) :241-261

[7] REARRANGEMENTS OF REGIOISOMERIC 4-ISOXAZOLINES - THE NOVEL FORMATION OF ENAMINE DERIVATIVES [J].

LIGUORI, A ;

OTTANA, R ;

ROMEO, G ;

SINDONA, G ;

UCCELLA, N .

TETRAHEDRON, 1988, 44 (04) :1255-1265

[8]

MAIOLI L, 1959, RIC SCI, V29, P1931

[9] DIPOLAR CYCLOADDITION REACTION OF (PHENYLSULFONYL)PROPADIENE WITH NITRONES AND ALKYLATION STUDIES OF THE CYCLOADDUCTS [J].

PADWA, A ;

CARTER, SP ;

CHIACCHIO, U ;

KLINE, DN .

TETRAHEDRON LETTERS, 1986, 27 (24) :2683-2686

[10] 1,3-DIPOLAR CYCLOADDITIONS OF NITRONES DERIVED FROM THE REACTION OF ACETYLENES WITH HYDROXYLAMINES [J].

PADWA, A ;

WONG, GSK .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3125-3133