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

[1] The mono-functionalization of symmetrical polyamines [J].

Bender, JA ;

Meanwell, NA ;

Wang, T .

TETRAHEDRON, 2002, 58 (16) :3111-3128

[2] In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide:: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid [J].

Blackburn, L ;

Kanno, H ;

Taylor, RJK .

TETRAHEDRON LETTERS, 2003, 44 (01) :115-118

[3] In situ oxidation-imine formation-reduction routes from alcohols to amines [J].

Blackburn, L ;

Taylor, RJK .

ORGANIC LETTERS, 2001, 3 (11) :1637-1639

[4]

BLITZ H, 1909, LIEBIGS ANN CHEM, V36, P262

[5] NUCLEOPHILIC CHARACTER OF ALKYL RADICALS .15. SELECTIVE HOMOLYTIC ALKYLATION OF QUINOXALINE BY N-CHLORO-AMINES - INFLUENCE OF MEDIUM ACIDITY [J].

CARONNA, T ;

CITTERIO, A ;

CROLLA, T ;

MINISCI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :865-869

[6] Enantiopure N-protected α-amino glyoxals 1.: Synthesis from α-amino acids and some condensation reactions with amines [J].

Darkins, P ;

Groarke, M ;

McKervey, MA ;

Moncrieff, HM ;

McCarthy, N ;

Nieuwenhuyzen, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :381-389

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

Dinsmore, CJ ;

Beshore, DC .

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

[8] 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

[9] 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

[10] 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

← 1 2 3 →