Synthesis of chiral 2,4-dichloro-6-menthoxy-1,3,5-triazines and 2- chloro-4,6-dimenthoxy-1,3,5-triazines as enantiodifferentiating coupling reagents. An x-ray study on 2,4,6-trimenthoxy-1,3,5-triazine

Synthetic Communications

Volumn 28, Issue 14, 1998, Pages 2689-2696

  Kamiński, Zbigniew J ^a   Markowicz, Stanisław W ^a   Kolesińska, Beata ^a   Martynowski, Dariusz ^a   Główka, Marek L ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 4,6 DIMENTHOXY 1,3,5 TRIAZINE; 2,4 DICHLORO 6 MENTHOXY 1,3,5 TRIAZINE; 2,4,6 TRIMENTHOXY 1,3,5 TRIAZINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHIRALITY; COUPLING FACTOR; CRYSTALLOGRAPHY; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; STRUCTURE ANALYSIS;

EID: 0040227797     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004839     Document Type: Article

References (27)

1. a) Wickramsinghe, N.S.M.D.; Lacey, J.C.Jr. Bioorg. Chem. 1992, 20, 265.
2. b) Markowicz, S.W.; Karolak-Wojciechowska, J. Pol. J. Chem. 1994, 68 1973.
3. c) Evans, D.A.; Anderson, J.C.; Taylor, M.K. Tetrahedron Lett. 1993, 34, 5563.
4. d) Goto, K.; Imamura, C.; Yamamoto, S.; Matsumoto, Y.; Ueoka, R. Chem. Lett. 1994, 2081.
5. e) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem Rev, 1996, 96, 835.
6. a) Akaji, K.; Kuriyama, N.; Kiso, Y. J. Org. Chem. 1996, 61, 3350.
7. b) Wipf, P., Venkatraman, S. Synlett, 1997, 1 and ref. cited therein.
8. Brueckner, H.; Strecker, B. Chromatographia, 1992, 33, 584.
9. b) ibid. J. Chromatogr. 1992, 627, 97.
10. c) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835.
11. a) Takeda, K.; Tsoboyama, K.; Suzuki, A.; Ogura, H. Chem. Pharm. Bull. 1985, 33, 2545.
12. b) Teramoto, T.; Deguchi, M.; Kurosaki, T.; Okawara, M. Tetrahedron Lett. 1981, 22, 1109.
13. Kamiński, Z.J.; Saleh, B.; Rudziński, J. 24-th Symposium of EPS, Edinburgh, 1996.
14. a) Kamiński, Z.J.; Paneth, P.; O'Leary, M. J. Org. Chem. 1991, 56. 5716.
15. b) Kaminski, Z.J. Int. J. Peptide Protein Res. 1994, 43, 312.
16. Yonehara, H.; Kang, W-B.; Kawara, T.; Pac, C. J. Mater. Chem. 1994, 4, 1571.
17. Venugopalan, P.; Buergi, H.B. Helv. Chim. Acta, 1994, 77, 1475.
18. Kaminski, Z.J.; Główka, M.L.; Olczak, A.; Martynowski, D. Polish J. Chem. 1997, 70, 1316.
19. Menicagli, R.; Malanga, C.; Peluso, P., Synth. Commun., 1994, 24(15), 2153.
20. Crude preparation has been evaporated to dryness, dissolved in toluene, washed with water, dried, and concentrated under reduced pressure prior the chromatographic resolution.
21. The coordinates, bond distances and angles are deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, Cambridge, UK, and can be obtained as a standard cif file from one of the authors (MLG) at the e-mail adress marekglo@ck-sg.p.lodz.pl.
22. Iwanicka, I. Ph.D. Thesis, Technical University of Łódź, 1989.
23. a) Główka, M.L.; Iwanicka, I. Acta Crystallogr. Section C, 1989, 45, 1765.
24. b) Krygowski, T.M.; Howard, S.T.; Martynowski, D.; Główka, M.L. J. Phys. Org. Chem. 1997, 10, 125.
25. Dudley, J.R.; Thurston, J.T.; Schaefer, F.C.; Holm-Hansen, D.; Hull, C.J.; Adams, P. J. Am. Chem. Soc. 1951, 73, 2986.
26. Beilstein-CrossFire Database.
27. Sheldrick, G.M.; SHELX93. Program for the Refinment of Crystal Structures. University of Göttingen, Göttingen 1993.