Reactivity of chlorodeoxypseudoephedrines with oxo-, thio-, and selenocyanates

Tetrahedron Asymmetry

Volumn 18, Issue 1, 2007, Pages 123-130

  Cruz, Alejandro ^a   Padilla Martínez, Itzia Irene ^a   García Báez, Efrén V ^a   Contreras, Rosalinda ^b  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 HETERAZOLIDINE 2 IMINIUM; 3,4 DIMETHYL 5 PHENYLOXAZOLIDINE 2 IMINIUM CHLORIDE; 4 METHYL 5 PHENYLOXAZOLINE 2 AMINE; 4 METHYL 5 PHENYLOXAZOLINE 2 AMMONIUM CHLORIDE; 4 METHYL 5 PHENYLSELENAZOLINE 2 AMINE; AMINE; AMMONIUM DERIVATIVE; AZIRIDINE; CYANIC ACID DERIVATIVE; EPHEDRINE DERIVATIVE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CIS ISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; TRANS ISOMER; X RAY DIFFRACTION;

EID: 33846847888     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.12.012     Document Type: Article

References (50)

1. Hunter R.F. J. Chem. Soc. 1 (1930) 125-147
2. Close W.J. J. Org. Chem. 15 (1950) 1131-1134
3. McCarthy W.C., and Ho B.-T. J. Org. Chem. 26 (1961) 4110-4112
4. Roth H.J., and Schlump S. Arch. Pharm. 4 (1963) 213
5. Fodor G., Stepanovsky J., and Kurtev B. Monatsh. Chem. 98 (1967) 1027-1042
6. Kniezo L., Kristian P., Budesinsky M., and Havrílová K. Collect. Czech. Chem. Commun. 46 (1981) 717-728
7. Evans D.A., Mathre D.J., and Scott W.L. J. Org. Chem. 50 (1985) 1830-1835
8. Noggle Jr. F.T., Clarck C.R., and De Ruiter J. J. Assoc. Off. Anal. Chem. Int. 75 (1992) 423-427
9. Cruz A., Flores-Parra A., Tlahuext H., and Contreras R. Tetrahedron: Asymmetry 6 (1995) 1933-1940
10. Cruz A., Macías-Mendoza D., Barragán-Rodríguez E., Tlahuext H., Nöth H., and Contreras R. Tetrahedron: Asymmetry 8 (1997) 3903-3911
11. Cruz A., Geníz E., and Contreras R. Tetrahedron: Asymmetry 9 (1998) 3991-3996
12. Cruz A., Vásquez-Badillo A., Ramos-García I., and Contreras R. Tetrahedron: Asymmetry 12 (2001) 711-717
13. Cruz A., Gayosso M., and Contreras R. Heteroat. Chem. 12 (2001) 586-593
14. Cruz A., and Juárez-Juárez M. Curr. Org. Chem. 8 (2004) 671-693
15. Cruz A., Contreras R., Padilla-Martínez I.I., and Juárez-Juárez M. Tetrahedron: Asymmetry 17 (2006) 1499-1505
16. Murakami M., and Fukumoto T. Nippon Kagaku Zasshi 76 (1955) 270
17. Pfanz H., and Kirchner G. Annalen 614 (1958) 149
18. Kojima M. Yakugaku Zasshi 79 (1959) 1
19. Roszkowski A.P., and Koelle G.B. J. Pharmacol. Exp. Ther. 128 (1960) 227
20. Poos G.I., Carson J.R., Rosenau J.R., Roszkouski A.P., Kelly N.M., and McGrowin J. J. Med. Chem. 5 (1963) 266
21. Trepanier D.L., and Sprancmanis V. J. Org. Chem. 29 (1964) 673
22. Trepanier D.L., and Sprancmanis V. J. Org. Chem. 29 (1964) 2151
23. Trepanier D.L., Sprancmanis V., and Wiggs K.G. J. Org. Chem. 29 (1964) 668
24. Trepanier, D. L. U.S. Patent 3,122,537, 1964.
25. Goodman L.S., and Gilman A. The Pharmacological Basis of Therapeutics. 3rd ed. (1965), Macmillan, New York, NY p 516
26. Trepanier D.L., Sprancmanis V., Tharpe D.S., and Krieger P.E. J. Heterocycl. Chem. 2 (1965) 403
27. Trepanier D.L., Kriger P.E., and Eble J.N. J. Med. Chem. 8 (1965) 802
28. Trepanier D.L., Reifschneider W., Shumaker W., and Tharpe D.S. J. Org. Chem. 30 (1965) 2228
29. Trepanier D.L., Sprancmanis V., and Eble J.N. J. Med. Chem. 9 (1966) 753
30. Cain C.K. Annual Reports in Medicinal Chemistry (1966), Academic Press, New York, NY p 54
31. Kalm, M. J. U.S. Patent 3,251,838, 1966.
32. Trepanier, D. L. U.S. Patent 3,290,303, 1966.
33. Trepanier D.L., Wagner E.R., Harris G., and Rudzik A.D. J. Med. Chem. 9 (1966) 881
34. Yuong-Harvey J.A., Rae I.D., and Pitman I.H. Int. J. Pharm. 30 (1986) 151
35. Chalina E., Dantchev D., Georgiev A., and Mitova K. Arch. Pharm. 319 (1986) 598
36. Buur A., and Bundgaar H. Arch. Pharm., Chem. Sci. Ed. 15 (1987) 76
37. Evans D.A., Ennis M.D., and Mathre D.J. J. Am. Chem. Soc. 104 (1982) 1737-1739
38. Sheldon R.A. Chirotechnology: Industrial Synthesis of Optically Active Compounds (1993), Marcel Dekker, New York pp 15-23, 135-137, 253-255
39. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835-875
40. Guillena G., and Nájera C. Tetrahedron: Asymmetry 9 (1998) 3935-3938
41. Guillena G., and Nájera C. J. Org. Chem. 65 (2000) 7310-7322
42. Bernabeu M.C., Chinchilla R., Falvello L.R., and Nájera C. Tetrahedron: Asymmetry 12 (2001) 1811-1815
43. Liu W.Q., Olszowy C., Bichoff L., and Garibay C. Tetrahedron Lett. 43 (2002) 1417-1419
44. Flores-Parra A., Suárez-Moreno P., Sánchez-Ruíz S., Tlahuextl M., Jaen-Gaspar J., Tlahuext H., Salas-Coronado R., Cruz A., Nöth H., and Contreras R. Tetrahedron: Asymmetry 9 (1998) 1661-1671
45. Nonius. KappaCCD Server Software. Windows 3.11 Version (1997), Nonius BV, Delft, The Netherlands
46. Otwinowski Z., and Minor W. Methods in Enzymology. In: Carter Jr. C.W., and Sweet R.M. (Eds). Macromolecular Crystallography, Part A Vol. 276 (1997), Academic Press, New York 307-326
47. Bruker. smart and saint. Versions 6.02a (2000), Bruker AXS, Madison, WI, USA
48. Sheldrick G.M. shelxs97 and shelxl97 (1997), University of Göttingen, Germany
49. Spek A.L. platon. Version of March 2002 (2002), University of Utrecht, The Netherlands
50. Farrugia L.J. J. Appl. Crystallogr. 32 (1999) 837-838