Hypervalent iodine oxidation of benzil-α-arylimino oximes: an efficient synthesis of 2,3-diphenylquinoxaline-1-oxides

Tetrahedron Letters

Volumn 47, Issue 28, 2006, Pages 4969-4971

  Aggarwal, Ranjana ^a   Sumran, Garima ^a   Saini, Anil ^a   Singh, Shiv P ^a  

^a KURUKSHETRA UNIVERSITY   (India)

Author keywords

2,3 diphenylquinoxaline 1 oxides; Benzil arylimino oximes; Hypervalent iodine; Iodobenzene diacetate; Oxidative cyclization

Indexed keywords

2,3 DIPHENYLQUINOXALINE 1 OXIDE; ANILINE DERIVATIVE; DICHLOROMETHANE; IODOBENZENE DIACETATE; OXIDIZING AGENT; OXIME DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; CYCLIZATION; OXIDATION; PROCESS DEVELOPMENT; QUANTUM YIELD; REACTION ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 33744813014     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.086     Document Type: Article

References (17)

1. Dell A., Williams D.H., Morris H.R., Smith G.A., Feeney J., and Roberts G.C.K. J. Am. Chem. Soc. 97 (1975) 2497-2502
2. Bailly C., Echepare S., Gago F., and Waring M.J. Anti-Cancer Drug Des. 14 (1999) 291-303
3. Sato K., Shiratori O., and Katagiri K. J. Antibiot. 20 (1967) 270-276 and references cited therein
4. Loriga M., Nuvole A., Paglietti G., Fadda G., and Zanetti S. Eur. J. Med. Chem. 25 (1990) 527-532
5. Aguirre G., Cerecetto H., Maio R.D., Gonzalez M., Alfaro M.E.M., Jaso A., Zarranz B., Ortega M.A., Aldana I., and Monge-Vega A. Bioorg. Med. Chem. 14 (2004) 3835-3839
6. Carta A., Paglietti G., Nikookar M.E.R., Sanna P., Sechi L., and Zanetti S. Eur. J. Med. Chem. 37 (2005) 355-366
7. Zarranz B., Jaso A., Aldana I., and Monge A. Bioorg. Med. Chem. 12 (2004) 3711-3721
8. Jaso A., Zarranz B., Aldana I., and Monge A. Eur. J. Med. Chem. 38 (2003) 791-800
9. Kim K.S., Qian L., Bird J.E., Dickinson K.E., Moreland S., Schaeffer T.R., Waldron T.L., Delaney C.L., Weller H.N., and Miller A.V. J. Med. Chem. 36 (1993) 2335-2342
10. Katritzky A.R., and Lagowski J.M. Chemistry of the Heterocyclic N-Oxides (1971), Academic Press, London
11. Porter A.E.A. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon, Oxford 157-196
12. Maroulis A.J., Domzaridou K.C., and Hadjiantoniou-Maroulis C.P. Synthesis (1998) 1769-1771
13. Prakash O., Kaur H., Batra H., Rani N., Singh S.P., and Moriarty R.M. J. Org. Chem. 66 (2001) 2019-2023
14. Aggarwal R., Pundeer R., Kumar V., Chaudhri V., Singh S.P., and Prakash O. Synth. Commun. 34 (2004) 2659-2664
15. Aggarwal R., and Sumran G. Synth. Commun. 36 (2006) 875-879
16. General procedure: To a stirred suspension (or) solution of 3 (1.0 mmol) in dichloromethane (20 ml) was added IBD (0.354 g, 1.1 mmol) in small portions over a period of 5 min at room temperature. The reaction mixture was allowed to stir until the colour of solution became red. The progress of reaction was monitored by TLC. When all the starting material had been consumed, excess dichloromethane was distilled off in vacuo to give a gummy residue containing the product and iodobenzene. The product 4 was isolated by column chromatography on silica gel [100-200 mesh] (iodobenzene was removed with petroleum ether and the product was eluted with petroleum ether-chloroform of increasing polarity). Quinoxaline-1-oxides 4 were recrystallized from aqueous ethanol.
17. 2O requires 350.0622).