Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes

被引：173

作者：

Raw, SA ^{[1
]}

Wilfred, CD ^{[1
]}

Taylor, RJK ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 18期

关键词：

D O I：

10.1039/b307177b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Hydroxyketones undergo MnO2-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one pot procedure which avoids the need to isolate the highly reactive 1,2-dicarbonyl intermediates. Modifications of the procedure allow the formation of pyrazines and piperazines.

引用

页码：2286 / 2287

页数：2

共 22 条

[11] Synthesis, structural evaluation, and estrogen receptor interaction of 2,3-diarylpiperazines [J].

Gust, R ;

Keilitz, R ;

Schmidt, K .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (11) :2325-2337

[12] OXIDATION OF DIAZO-COMPOUNDS BY DIMETHYL DIOXIRANE - AN EXTREMELY MILD AND EFFICIENT METHOD FOR THE PREPARATION OF LABILE ALPHA-OXO-ALDEHYDES [J].

IHMELS, H ;

MAGGINI, M ;

PRATO, M ;

SCORRANO, G .

TETRAHEDRON LETTERS, 1991, 32 (43) :6215-6218

[13]

JENNESKENS LW, 1995, RECL TRAV CHIM PAY B, V114, P97

[14]

LABLACHE.A, 1974, B SOC CHIM FR II-CH, P225

[15] CONVERSION OF VICINAL DIOLS INTO DICARBONYL-COMPOUNDS BY MANGANESE-DIOXIDE [J].

OHLOFF, G ;

GIERSCH, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (05) :401-402

[16]

OHTA A, 1982, J HETEROCYCLIC CHEM, V19, P1061, DOI 10.1002/jhet.5570190517

[17] In situ oxidative diol cleavage-Wittig processes [J].

Outram, HS ;

Raw, SA ;

Taylor, RJK .

TETRAHEDRON LETTERS, 2002, 43 (35) :6185-6187

[18] The in situ oxidation-Wittig reaction of α-hydroxyketones [J].

Runcie, KA ;

Taylor, RJK .

CHEMICAL COMMUNICATIONS, 2002, (09) :974-975

[19]

SAKATA G, 1988, HETEROCYCLES, V27, P2481

[20]

SATO N, 1996, COMPREHENSIVE HETE 2, V6

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