One-pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives using β-cyclodextrin as reusable catalyst in water

Tetrahedron Letters

Volumn 51, Issue 28, 2010, Pages 3649-3653

  Murthy, S Narayana ^a   Madhav, B ^a   Reddy, V Prakash ^a   Nageswar, Y V D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Cyclodextrin; Condensation; Diethyl phosphonate; Ethyl cyanoacetate; Malononitrile; Salicylaldehyde; Triethyl phosphate; Water

Indexed keywords

2 AMINO 4H CHROMEN 4 YLPHOSPHONATE DERIVATIVE; ALDEHYDE DERIVATIVE; BETA CYCLODEXTRIN; CHROMENE DERIVATIVE; MALONONITRILE; NITRILE; PHOSPHONIC ACID DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77954348895     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.028     Document Type: Article

References (20)

1. D.V. Patel, K. Rielly-Gauvin, and D.E. Ryono Tetrahedron Lett. 31 1990 5587
2. B. Stowasser, K.H. Budt, J.Q. Li, A. Peyman, and D. Ruppert Tetrahedron Lett. 33 1992 6625
3. E.K. Baylis, C.D. Campbell, and J.G. Dingwall J. Chem. Soc., Perkin Trans. 1 1984 2845
4. F.R. Atherton, C.H. Hassall, and R.W. Lambert J. Med. Chem. 29 1986 29
5. K.A. Schug, and W. Lindner Chem. Rev. 105 2005 67
6. K. Moonen, I. Laureyn, and C.V. Stevens Chem. Rev. 104 2004 6177
7. F. Palacios, C. Alonso, and J.M. De Los Santos Curr. Org. Chem. 8 2004 1481
8. E.A. Hafez, M.H. Elnagdi, A.A. Elagamey, and F.A.M. El-Taweel Heterocycles 26 1987 903
9. G.P. Ellis A. Weissberger, E.C. Taylor, The Chemistry of Heterocyclic Compounds. Chromenes, Harmones, and Chromones 1977 John Wiley New York 11 139 Chapter II
10. M.A. Sofan, F.M.A. El-Taweel, and M.H. Elnagdi Liebigs Ann. Chem. 1989 935
11. F.M. Abdel Galil, B.Y. Riad, S.M. Sherif, and M.H. Elnagdi Chem. Lett. 1982 1123
12. S.G. Das, J.M. Doshi, D. Tian, S.N. Addo, B. Srinivasan, D.L. Hermanson, and C. Xing J. Med. Chem. 52 2009 5937
13. J.M. Doshi, D. Tian, and C. Xing J. Med. Chem. 49 2006 7731
14. P. Jayashree, G. Shanthi, and P.T. Perumal Synlett 2009 917
15. S.N. Murthy, B. Madhav, A.V. Kumar, K.R. Rao, and Y.V.D. Nageswar Tetrahedron 65 2009 5251
16. B. Madhav, S.N. Murthy, V.P. Reddy, K.R. Rao, and Y.V.D. Nageswar Tetrahedron Lett. 50 2009 6025
17. S.N. Murthy, B. Madhav, A.V. Kumar, K.R. Rao, and Y.V.D. Nageswar Helv. Chim. Acta 92 2009 2118
18. B. Madhav, S.N. Murthy, K.R. Rao, and Y.V.D. Nageswar Helv. Chim. Acta 93 2010 257
19. 4. The combined organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate and hexane (7:3) as eluent to give the corresponding 2-amino-3-cyano-4H-chromen-4-yl phosphonate as pure products in good yields.
20. +.