Efficient Synthesis of Some New 2,3-Dimethylquinoxaline-1-oxides Using Bis(acetoxy)phenyl-λ³-iodane as an Oxidant

REFERENCES

• (a) Yan , L. ; Liu , F. W. ; Dai , G. F. ; Liu , H. M. An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-α-D-galactose and their cytotoxic activities . Bioorg. Med. Chem. Lett. 2007 , 17 , 609 – 612 ; (b) Saari , R. ; Torma , J. C. ; Nevalainen , T. Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline, and quinazoline derivatives as CB2 receptor agonists . Bioorg. Med. Chem. 2011 , 19 , 939 – 950 .
   PubMed Web of Science ®Google Scholar
• (a) Barea , C. ; Pabon , A. ; Castillo , D. ; Zimic , M. ; Quiliano , M. ; Galiano , S. ; Perez-Silanes , S. ; Monge , A. ; Deharo , E. ; Aldana , I. New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities. Bioorg. Med. Chem. Lett. 2011, 21, 4498–4502; (b) Burguete , A. ; Pontiki , E. ; Hadjipavlou-Litina , D. ; Villar , R. ; Vicente , E. ; Solano , B. ; Ancizu , S. ; Perez-Silanes , S. ; Aldanaa , I. ; Mongea , A. Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues. Bioorg. Med. Chem. Lett. 2007, 17, 6439–6443; (c) Estevez , Y. ; Quiliano , M. ; Burguete , A. ; Cabanillas , B. ; Zimic , M. ; Malaga , E. ; Verastegui , M. ; Perez-Silanes , S. ; Aldana , I. ; Monge , A. ; Castillo , D. ; Deharo , E. Trypanocidal properties, structure–activity relationship, and computational studies of quinoxaline 1,4-di-N-oxide derivatives. Exp. Parasitol. 2011, 127, 745–751; (d) Ismail , M. M. F. ; Amin , K. M. ; Noaman , E. ; Soliman , D. H. ; Ammar , Y. A. New quinoxaline 1,4-di-N-oxides: Anticancer and hypoxia-selective therapeutic agents. Eur. J. Med. Chem. 2010, 45, 2733–2738; (e) Moreno , E. ; Perez-Silanes , S. ; Gouravaram , S. ; Macharam , A. ; Ancizu , S. ; Torres , E. ; Aldana , I. ; Monge , A. ; Crawford , P. W. 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure, and anti-tuberculosis activity. Electrochim. Acta 2011, 56, 3270–3275; (f) Moreno , E. ; Ancizu , S. ; Perez-Silanes , S. ; Torres , E. ; Aldana , I. ; Monge , A. Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives. Eur. J. Med. Chem. 2010, 45, 4418–4426 (g) Jaso , A. ; Zarranz , B. ; Aldana , I. ; Monge , A. Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti–Mycobacterium tuberculosis agents. J. Med. Chem. 2005, 48, 2019–2025.
   PubMed Web of Science ®Google Scholar
• (a) Johnston , J. D. ; Chas Pfizer and Co. Inc. Novel antibacterial agents. Patent U.S. 3371090 , February 27 , 1968 ; (b) Haddadin , M. J. ; Issidorides , C. H. ; Lebanon , B. ; Research Corp. Quinoxaline-di-N-oxides. Patent U.S. 3398141, August 20, 1968 ; (c) Haddadin , M. J. ; Kattan , A. M. A. ; Issidorides , C. H. Oxidative elimination of nitrous acid from nitrate esters: Preparation of mecadox . J. Org. Chem. 1985 , 50 , 129 – 130 .
   Google Scholar
• Edwards , M. L. ; Bambury , R. E. ; Ritter , H. W. β-Lactam antibiotics with N-oxide side chains, 1: Quinoxaline N-oxides . J. Med. Chem. 1976 , 19 , 330 – 333 .
   PubMed Web of Science ®Google Scholar
• Kim , H. K. Richardson-Merrel Inc. 1,4-Dioxidoquinoxalinyl nitrones. Patent U.S. 3644363, February 22, 1972 .
   Google Scholar
• (a) Brown , D. J. The chemistry of heterocyclic compounds . Quinoxalines 2004 , 61 ; (b) Katritzky , A. R. ; Boulton , A. J. Advances in heterocyclic Chemistry; Academic Press: New York, 1978; vol. 22, pp. 390–392 .
   Google Scholar
• Grovenstein , E. ; Postman , W. ; Taylor , J. W. Reaction of 2-phenylquinoxaline and of 2,3-diphenylquinoxaline with dimethyl acetylenedicarboxylate . J. Org. Chem. 1960 , 25 , 68 – 73 .
   Web of Science ®Google Scholar
• Kluge , A. F. ; Maddox , M. L. ; Lewis , G. S. Formation of quinoxaline monoxides from reaction of benzofurazan oxide with enones and C-13 NMR correlations of quinoxaline N-oxides . J. Org. Chem. 1980 , 45 , 1909 – 1914 .
   Web of Science ®Google Scholar
• Maroulis , A. J. ; Domzaridou , K. C. ; Hadjiantoniou–Maroulis , C. P. Synthesis of 2,3-diphenylquinoxaline-1-oxides by oxidative cyclization of benzyl-α-arylimino oximes . Synthesis 1998 , 1769 – 1771 .
   Web of Science ®Google Scholar
• Aggarwal , R. ; Sumran , G. ; Saini , A. ; Singh , S. P. Hypervalent iodine oxidation of benzil-α-arylimino oximes: An efficient synthesis of 2,3-diphenylquinoxaline-1-oxides . Tetrahedron Lett. 2006 , 47 , 4969 – 4971 .
   Web of Science ®Google Scholar
• Zangrando , E. ; Trani , M. ; Stabon , E. ; Carfagna , C. ; Milani , B. ; Mestroni , G. Synthesis and molecular structures of nickel(II) and cobalt(II) complexes with 2-(arylimino)-3-(hydroxyimino)butane . Eur. J. Inorg. Chem. 2003 , 14 , 2683 – 2692 .
   Web of Science ®Google Scholar