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

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 modifications to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

[1]  R. Taylor,et al.  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 , 2003 .

[2]  R. Reynolds,et al.  Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives. , 2002, Journal of medicinal chemistry.

[3]  A. Fürstner,et al.  Iron-catalyzed cross-coupling reactions. , 2002, Journal of the American Chemical Society.

[4]  R. Taylor,et al.  A one-pot oxidation–imine formation–reduction route from alcohols to amines using manganese dioxide–sodium borohydride: the synthesis of naftifine , 2002 .

[5]  S. A. Raw,et al.  In situ oxidative diol cleavage–Wittig processes , 2002 .

[6]  R. Gust,et al.  Synthesis, structural evaluation, and estrogen receptor interaction of 2,3-diarylpiperazines. , 2002, Journal of medicinal chemistry.

[7]  D. Beshore,et al.  Recent advances in the synthesis of diketopiperazines , 2002 .

[8]  N. Meanwell,et al.  The mono-functionalization of symmetrical polyamines , 2002 .

[9]  S. Spergel,et al.  Biphenylsulfonamide endothelin receptor antagonists. Part 3: structure-activity relationship of 4'-heterocyclic biphenylsulfonamides. , 2002, Bioorganic & medicinal chemistry letters.

[10]  M. J. Bishop,et al.  2-(anilinomethyl)imidazolines as alpha1A adrenergic receptor agonists: 2'-heteroaryl and 2'-oxime ether series. , 2002, Bioorganic & medicinal chemistry letters.

[11]  Jennifer S. Gibson,et al.  The scope and limitations of deuteration mediated by Crabtree's catalyst , 2001 .

[12]  Taylor,et al.  In situ manganese dioxide alcohol oxidation-wittig reactions: preparation of bifunctional dienyl building blocks , 2000, The Journal of organic chemistry.

[13]  Kenji Watanabe,et al.  New compounds derived from dihydropyrazines having DNA strand-breakage activity , 1999 .

[14]  G. Mcmahon,et al.  Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins. , 1996, Journal of medicinal chemistry.

[15]  D. Villemin,et al.  Synthesis of Quinoxalines Under Focussed Microwave Irradiation , 1995 .

[16]  A. Gueiffier,et al.  Heterocyclizations in the pyrido[2,3-b]pyrazine series , 1994 .

[17]  P. Darke,et al.  Potent HIV protease inhibitors: the development of tetrahydrofuranylglycines as novel P2-ligands and pyrazine amides as P3-ligands. , 1993, Journal of medicinal chemistry.

[18]  Daniel M. Bender,et al.  An enantioselective synthesis of vicinal diamines , 1992 .

[19]  R. Moriarty,et al.  Direct α-hydroxylation of ketones under acidic conditions using [bis (trifluoroacetoxy)] iodobenzene , 1992 .

[20]  K. Gollnick,et al.  Photooxygenation of 1,4-diaza-1,3-butadienes (.alpha.-diimines): formation of isonitriles , 1992 .

[21]  M. Prato,et al.  Oxidation of diazo compounds by dimethyl dioxirane: an extremely mild and efficient method for the preparation of labile α-oso-aldehydes , 1991 .

[22]  P. Steel,et al.  Cyclometallated compounds. V, Double cyclopalladation of diphenyl pyrazines and related ligands , 1990 .

[23]  S. Freedman,et al.  Synthesis and biological activity of 1,2,4-oxadiazole derivatives: highly potent and efficacious agonists for cortical muscarinic receptors. , 1990, Journal of medicinal chemistry.

[24]  K. Makino,et al.  Regent progress in the quinoxaline chemistry. Synthesis and biological activity , 1988 .

[25]  D. Norbeck,et al.  Application of the Swern oxidation to the manipulation of highly reactive carbonyl compounds , 1985 .

[26]  T. Nishio.  The (2 + 2) photocycloaddition of the carbon-nitrogen double bond of quinoxalin-2(1H)-ones to electron-deficient olefins , 1984 .

[27]  S. Patt,et al.  Synthesis and biological properties of thiophene ring analogues of mianserin. , 1983, Journal of medicinal chemistry.

[28]  A. Ohta,et al.  SOME REACTIONS OF MONO SUBSTITUTED PYRAZINE MONOXIDES , 1982 .

[29]  J. Pinson,et al.  Electrochemical reduction of pyridopyrazines , 1978 .

[30]  G. Ohloff,et al.  Conversion of Vicinal Diols into Dicarbonyl Compounds by Manganese Dioxide , 1973 .

[31]  J. Karliner,et al.  Lactam Formation from the Condensation of Stilbenediamine with Glyoxal , 1971 .

[32]  M. V. George,et al.  Oxidation with metal oxides. III. Oxidation of diamines and hydrazines with manganese dioxide , 1968 .

[33]  J. W. Taylor,et al.  Reaction of 2-Phenylquinoxaline and of 2,3-Diphenylquinoxaline with Dimethyl Acetylenedicarboxylate1 , 1960 .