AN EASY ACCESS TO 2-OXOHYDRAZONES VIA ELECTROPHILIC ALPHA-P-TOLYLHYDRAZONYLATION OF KETONE ENOLATES WITH TERT-BUTYL P-TOLYLAZO SULFIDE

被引：10

作者：

DELLERBA, C

NOVI, M

PETRILLO, G

TAVANI, C

机构：

[1] Istituto di Chimica Organica dell'Università, C.N.R. Centro di Studio per la Chimica dei Composti Cicloalifatici ed Aromatici, 16132

来源：

TETRAHEDRON | 1994年 / 50卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(01)89426-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title reaction conveniently furnishes, as the sole or main products, alpha-(p-tolylhydrazono)ketones or their N-methylderivatives (H+ or Mel quenching of the final mixture, respectively). Although the method fails with ketones having a secondary alkyl group bonded to the carbonyl, yields are otherwise more than satisfactory and particular interest is attached to the hydrazonylation of the methyl group in methyl ketones.

引用

页码：11239 / 11248

页数：10

共 54 条

[21] ENANTIOSELECTIVE SYNTHESIS OF PROTECTED ALPHA-HYDROXY ALDEHYDES AND KETONES VIA HYDROXYLATION OF METALATED CHIRAL HYDRAZONES [J].

ENDERS, D ;

BHUSHAN, V .

TETRAHEDRON LETTERS, 1988, 29 (20) :2437-2440

[22] ENANTIOSELECTIVE SYNTHESIS OF 2-SULFENYLATED ALDEHYDES - ALKYLATION OF SULFENYLATED ACETALDEHYDE SAMP-HYDRAZONES [J].

ENDERS, D ;

SCHAFER, T ;

PIVA, O ;

ZAMPONI, A .

TETRAHEDRON, 1994, 50 (11) :3349-3362

[23]

Enders D., 1983, ASYMMETRIC SYNTHES B, V3, P275

[24]

ENDERS E, 1965, METHODEN ORGANISCHEN, V10, P490

[25] A NOVEL SYNTHESIS OF (E)-3,7-DIMETHYL-2-OCTENE-1,8-DIOL SECRETED BY THE AFRICAN MONARCH USING THE RING-OPENING REACTION OF ALPHA-METHYL-BETA-PROPIOLACTONE [J].

FUJISAWA, T ;

SATO, T ;

KAWARA, T ;

NODA, A .

TETRAHEDRON LETTERS, 1982, 23 (31) :3193-3194

[26] 1,3-DIPOLAR CYCLOADDITIONS .12. SYNTHESIS OF 1,3,4-THIADIAZOLIDINE-5-THIONES [J].

GRASHEY, R ;

HUISGEN, R ;

SUN, KK .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (01) :74-&

[27]

HAFEZ EAA, 1984, HETEROCYCLES, V22, P1821

[28]

JACKSON A, 1967, J CHEM SOC CHEM COMM, P459

[29]

KAMITORI Y, 1990, SYNTHESIS-STUTTGART, P491

[30]

KAMITORI Y, 1988, SYNTHESIS-STUTTGART, P208

← 1 2 3 4 5 6 →