Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds

被引：211

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：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 05期

关键词：

D O I：

10.1039/b315689c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Hydroxy ketones undergo manganese dioxide-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 dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modi. cations to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

引用

页码：788 / 796

页数：9

共 44 条

[11] LACTAM FORMATION FROM CONDENSATION OF STILBENEDIAMINE WITH GLYOXAL [J].

DARKO, LL ;

KARLINER, J .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (24) :3810-&

[12] Recent advances in the synthesis of diketopiperazines [J].

Dinsmore, CJ ;

Beshore, DC .

TETRAHEDRON, 2002, 58 (17) :3297-3312

[13] The scope and limitations of deuteration mediated by Crabtree's catalyst [J].

Ellames, GJ ;

Gibson, JS ;

Herbert, JM ;

McNeill, AH .

TETRAHEDRON, 2001, 57 (46) :9487-9497

[14] Iron-catalyzed cross-coupling reactions [J].

Fürstner, A ;

Leitner, A ;

Méndez, M ;

Krause, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13856-13863

[15] Tyrphostins .5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins [J].

Gazit, A ;

App, H ;

McMahon, G ;

Chen, J ;

Levitzki, A ;

Bohmer, FD .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (11) :2170-2177

[16] POTENT HIV PROTEASE INHIBITORS - THE DEVELOPMENT OF TETRAHYDROFURANYLGLYCINES AS NOVEL P(2)-LIGANDS AND PYRAZINE AMIDES AS P(3)-LIGANDS [J].

GHOSH, AK ;

THOMPSON, WJ ;

HOLLOWAY, MK ;

MCKEE, SP ;

DUONG, TT ;

LEE, HY ;

MUNSON, PM ;

SMITH, AM ;

WAI, JM ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (16) :2300-2310

[17] PHOTOOXYGENATION OF 1,4-DIAZA-1,3-BUTADIENES (ALPHA-DIIMINES) - FORMATION OF ISONITRILES [J].

GOLLNICK, K ;

KOEGLER, S ;

MAURER, D .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :229-234

[18]

GROVENSTEIN PT, 1960, J ORG CHEM, V25, P68

[19] 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

[20] 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

← 1 2 3 4 5 →