Ionic Liquid-Promoted Phospha-Michael Reaction: Convenient Access to β-Nitrophosphonates

Synthetic Communications

Volumn 45, Issue 18, 2015, Pages 2083-2091

  Jayaprakash, S H ^a   Satheesh Krishna, B ^a   Santhi Sudha, S ^a   Bakthavatchala Reddy, N ^a   Sreelakshmi, P ^a   Kumar Reddy, K Madhu ^a   Suresh Reddy, C ^a  

^a SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

C P bond formation; ionic liquid; phospha Michael addition; DBUH OAc

Indexed keywords

DICYCLOHEXYLCARBODIIMIDE; IONIC LIQUID; LEWIS BASE; NITROGEN DERIVATIVE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; STYRENE DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CATALYST; ELECTROPHILICITY; MICHAEL ADDITION; NUCLEOPHILICITY; REACTION TIME; TEMPERATURE;

EID: 84939651495     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2015.1064138     Document Type: Article

References (26)

1. Engel, R. Phosphonates as analogues of natural phosphates. Chem. Rev. 1977, 77, 349.
2. Allen, M. C., Fuhrer, W., Tuck, B., Wade, R., Wood, J. M. Renin inhibitors: Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond. J. Med. Chem. 1989, 32, 1652.
3. Conrad, K. A., Lee, S. M. Clodronate kinetics and dynamics. Clin. Pharmacol. Ther. 1981, 30, 114.
4. Corbridge, D. E. C. Phosphorus: An Outline of Its Chemistry, Biochemistry, and Uses, 5th ed.; Elsevier: Amsterdam, 1995.
5. Rao, K. U. M., Jayaprakash, S. H., Nayak, S. K., Reddy, C. S. Polyethylene glycol in water: A simple and environmentally friendly medium for C-P bond formation. Catal. Sci. Technol. 2011, 1, 1665.
6. Rajeshwaran, G. G., Nandakumar, M., Sureshbabu, R., Mohanakrishnan, A. K. Lewis acid-mediated Michaelis-Arbuzov reaction at room temperature: A facile preparation of arylmethyl/heteroarylmethyl phosphonates. Org. Lett. 2011, 13, 1270.
7. Beck, J., Gharbi, S., Adriana, H. F., Vercheval, L., Bebrone, C., Lassaux, P., Zervosen, A., Jacqueline, M. B. Aminophosphonic acids and aminobis(phosphonic acids) as potential inhibitors of penicillin-binding proteins. Eur. J. Org. Chem. 2009, 1, 85.
8. Prasad, S. S., Kumar, K. S., Jayaprakash, S. H., Krishna, B. S., Syama Sundar, Ch., Rao, P. V., Babu, T. M., Rajendra, W., Reddy, C. S. Design, synthesis, antioxidant, and anti-breast cancer activities of novel diethyl(alkyl/aryl/heteroarylamino)(4-(pyridin-2-yl)phenyl)methylphosphonates. Arch. Pharm. Chem. Life Sci. 2013, 346, 380.
9. Amol, H. K., Rajkumar, U. P., Swapnil, S. S., Vaibhav, U. G., Bapurao, B. S., Murlidhar, S. S. Synthesis, in vitro antibacterial, and antifungal evaluations of new alpha-hydroxyphosphonate and new alpha-acetoxyphosphonate derivatives of tetrazolo [1, 5-a]quinolone. Eur. J. Med. Chem. 2010, 45, 1128.
10. Enders, D., Saint-Dizier, A., Lannou, M. I., Lenzen, A. The phospha-Michael addition in organic synthesis. Eur J. Org Chem. 2006, 1, 29.
11. Bartoli, G., Bosco, M., Carlone, A., Locatelli, M., Mazzanti, A., Sambri, L., Melchiorre, P. Organocatalytic asymmetric hydrophosphination of nitroalkenes. Chem. Commun. 2007, 7, 722.
12. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
13. Thomas, A. A., Sharpless, K. B. The catalytic asymmetric aminohydroxylation of unsaturated phosphonates. J. Org. Chem. 1999, 64, 8379.
14. Palacios, F., Alonso, C., De Los Santos, J. M. Synthesis of beta-aminophosphonates and-phosphonates. Chem. Rev. 2005, 105, 899.
15. Kukhar, V. P., Hudson, H. R. Aminophosphonic and Aminophosphonic Acids: Chemistry and Biological Activity; Wiley: New York, 2000.
16. Wang, J., Lora, D. H., Hao, L., Liansuo, Z., Wei, J., Hexin, X., Wei, W. Quinine-catalyzed enantioselective Michael addition of diphenyl phosphite to nitroolefins: Synthesis of chiral precursors of α-substituted β-aminophosphonates. Adv. Synth. Catal. 2007, 349, 1052.
17. Zhiyong, J., Yan, Z., Weiping, Y., Tan, C. H. P-C bond formation via direct and three-component conjugate addition catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Tetrahedron Lett. 2007, 48, 51.
18. Vishal, R., Namboothiri, N. Enantioselective conjugate addition of dialkyl phosphites to nitroalkenes. Tetrahedron: Asymmetry 2008, 19, 2335.
19. Santhi, A., Mayur, B., Zhao, C. G. Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: Beneficial effects of molecular sieves. Tetrahedron 2011, 67, 7479.
20. Qi, X., Watanabe, M., Aida, T. M., Smith, R. L. Efficient one-pot production of 5-hydroxymethylfurfural from inulin in ionic liquids. Green Chem. 2010, 12, 1855.
21. Kurosh, R. M., Seyyedeh, C. A., Esmayeel, A. G. Synthesis of novel pyrano[3,2-c]quinoline-2,5-diones using an acidic ionic liquid catalyst. Tetrahedron Lett. 2013, 54, 4633.
22. Wang, W., Shao, L., Cheng, W., Yang, J., He, M. Brønsted acidic ionic liquids as novel catalysts for Prins reaction. Catal. Commun. 2008, 9, 337.
23. Bo, Y., Hongye, Z., Yanfei, Z., Sha, C., Jilei, X., Leiduan, H., Zhimin, L. DBU-based ionic-liquid-catalyzed carbonylation of o-phenylenediamines with CO 2 to 2-benzimidazolones under solvent-free conditions. ACS Catal. 2013, 3, 2076.
24. Ying, A. G., Liu, L., Wu, G. F., Chen, G., Chen, X. Z., Ye, W. D. Aza-Michael addition of aliphatic or aromatic amines to α, β-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions. Tetrahedron Lett. 2009, 50, 1653.
25. Guthrie, J. P. Tautomerization equilibria for phosphorous acid and its ethyl esters, free energies of formation of phosphorous and phosphonic acids and their ethyl esters, and pKa values for ionization of the P-H bond in phosphonic acid and phosphonic esters. Can. J. Chem. 1979, 57, 236.
26. Tsutomu, I. Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes, and Related Organocatalysts; John Wiley & Sons: London, 2009.