Synthesis of quinoxaline 1,4-di-N-oxide analogues and crystal structure of 2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide

Molecules

Volumn 16, Issue 8, 2011, Pages 6894-6901

  Xu, Yingjun ^a   Wu, Fanhong ^a   Yao, Zhiyi ^a   Zhang, Minmin ^a   Jiang, Sheng ^a  

^a SHANGHAI INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Acyloin endiol tautomerism; Beirut reaction; Quinoxaline 1,4 di N oxide

Indexed keywords

ANTIINFECTIVE AGENT; BIOLOGICAL PRODUCT; ESTER; KETONE; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTI-INFECTIVE AGENTS; BIOLOGICAL AGENTS; CRYSTALLOGRAPHY, X-RAY; ESTERS; ISOMERISM; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUINOXALINES;

EID: 80052241976     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16086894     Document Type: Article

References (19)

1. Johnsbon, J.D.; Saybrock, O. Novel Antibacterial Agents. U.S. Patent 3,371,090, 27 February1968.
2. Dirlam, J.P.; Presslitz, J.E.; Williams, B.J. Synthesis and antibacterial activity of some 3-[(alkylthio)methyl]quinoxaline 1-oxide derivatives. J. Med. Chem. 1983, 26, 1122-1128.
3. Andrés, J.; Belén, Z.; Ignacio, A. Synthesis of New Quinoxaline-2-carboxylate 1,4-Dioxide Derivatives as Anti-Mycobacterium tuberculosis Agents. J. Med. Chem. 2005, 48, 2019-2024.
4. Issidorides, C.H.; Haddadin, M.J. Quinoxaline derivatives. U.S. Patent 4,343,942, 10 August 1982.
5. Haddadin, M.J.; Issidorides, C.H. Enamines with isobenzofuroxan: A novel synthesis of quinoxaline-di-N-oxide. Tetrahedron Lett. 1965, 36, 3253-3256.
6. Issidorides, C.H.; Haddadin, M.J. Benzofurazan oxide: II Reactions with enolate anions. J. Org. Chem. 1966, 31, 4067-4068.
7. Lin, S. Syntheses and spectroscopic investigations on eleven 2,3-disubstituted quinoxaline-1,4-dioxide antibiotics. Appl. Chem. 1988, 5, 17-23.
8. Lin, S.; Wang, H. An improved method for synthesis of substituted quinoxaline-1,4-dioxides. Youji Huaxue. 1986, 298-303.
9. Zhang, D.L.; Liang, J.P.; Liu, Y.; Wang, X.H.; Hua, L.Y. Synthesis and antibacterial activity of quinoxalines 1,4-di-N-oxide. Chinese J. Pharm. 2008, 39, 410-412.
10. Ley, K.; Eholzer, U.; Nast, R.; Seng, F. Preparation of Quinoxaline-di-N-oxides. U.S. Patent 3,660,398, 1972.
11. Wang, J.L.; Liu, F.C. Synthesis of biscarbonyl side chain substituted quinoxaline-1,4-dioxide. Hecheng Huaxue 1996, 4, 171-173.
12. Simone, C.A.; Silva, R.P.; Goulart, M.; Silva, R,; Lobato, A.P.; Pinto, M.C.; Pinto, A.V. Synthesis and crystal structure of the N4-oxide of an hydroxybenzo[f]quinoxalin-6(5H)-one obtained by oxidative cleavage of beta-lapachone-quinoxaline. J. Chem. Crystallography 2006, 36, 551-556. (Pubitemid 44483458)
13. Sheldrick, G.M. SHELXS-97. Acta Cryst. 1990, A46, 467-475
14. DIRDIF94: Beurskens, P.T.; Admiraal, G.; Beurskens, G.; Bosman, W.P.; Garcia-Granda, S.; Gould, R.O.; Smits, J.M.; Smykalla, C. The DIRDIF-94 Program System; Technical Report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1994.
15. Cromer, D.T.; Waber, J.T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, UK, 1974; Volume 4, Table 2.2 A.
16. Ibers, J.A.; Hamiton, W.C. Dispersion corrections and crystal structure refinements. Acta Cryst. 1964, 17, 781.
17. Creagh, D.C.; McAuley, W.J. International Tables for Crystallography; Wilson, A.J., Ed.; Kluwer Academic Publishers: Boston, MA, USA, 1992; Volume C, pp. 219-222, Table 4.2.6.3.8.
18. Creagh, D.C. and Hubbell, J.H. International Tables for Crystallography; Wilson, A.J., Ed.; Kluwer Academic Publishers: Boston, MA, USA, 1992; Volume C, pp. 200-206, Table 4.2.4.3.
19. TeXsan: Crystal Structure Analysis Package; Molecular Structure Corporation: The Woodlands, TX, USA, 1985.