Novel betaines of the hexaalkylguanidinio-carboxylate type

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 64, Issue 11-12, 2009, Pages 1617-1624

  Walter, Matthias ^a   Maas, Gerhard ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Betaines; Guanidinium; Isonipecotic acid; Nipecotic acid; Piperidinecarboxylic acids

Indexed keywords

CARBOXYLATION; DICHLOROMETHANE;

4-PIPERIDINECARBOXYLIC ACID; ALKALINE CLEAVAGE; DICARBOXYLATES; GUANIDINIUM; LOW MELTING POINT; METHYL ESTERS; NIPECOTIC ACID; NUCLEOPHILIC SUBSTITUTIONS;

BETAINES;

EID: 73849084462     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2009-11-1248     Document Type: Article

References (41)

1. F. J. de Zwart, S. Slow, R. J. Payne, M. Lever, P. M. George, J. A. Gerrard, S. T. Chambers, Food Chem. 2003, 83, 197 - 204.
2. a) L. N. Csonka, Microbiol. Rev. 1989, 53, 121 - 147;
3. b) M. Ashraf, M. R. Foolad, Environ. Exp. Bot. 2006, 59, 206 - 216;
4. c) T. H. H. Chen, N. Murata, Trends in Plant Science 2008, 13, 499 - 505;
5. d) J. M. Wood, Microbiol. Mol. Biol. Rev. 1999, 63, 230 - 262.
6. a) W. Henke, K. Herdel, K. Jung, D. Schnorr, S. A. Loening, Nucleic Acids Res. 1997, 25, 3957 - 3958;
7. b) M. Ralser, R. Querfurth, H.-J. Warnatz, H. Lehrach, M.-L. Yaspo, S. Krobitsch, Biochem. Biophys. Res. Commun. 2006, 347, 747 - 751.
8. K. Koumoto, H. Ochiai, N. Sugimoto, Tetrahedron 2008, 64, 168 - 174.
9. L. Rigano, G. Dell'Acqua, R. Leporatti, Cosmetics & Toiletries 2000, 115, 47 - 54.
10. nd ed., Surfactant Science Series 59, Marcel Dekker, New York, 1996.
11. H. Kunkel, G. Maas, Eur. J. Org. Chem. 2007, 3746-3757.
12. a) J. Cardoso, A. Huanosta, O. Manero, Macromolecules 1991, 24, 2890 - 2895;
13. b) M. Galin, A. Mathis, J.-C. Galin, Polym. Adv. Technol. 2001, 12, 574 - 582, and refs. cited therein.
14. a) M. Yoshizawa, M. Hirao, K. Ito-Akita, H. Ohno, J. Mater. Chem. 2001, 11, 1057 - 1062;
15. b) M. Yoshizawa, A. Narita, H. Ohno, Aust. J. Chem. 2004, 57, 139 - 144;
16. c) M. Yoshizawa, H. Ohno, Chem. Lett. 2004, 33, 1594 - 1595;
17. d) account: H. Ohno, Bull. Chem. Soc. Jpn. 2006, 79, 1665 - 1680;
18. e) J. N. Krishnan, H. S. Kim, J. K. Lee, B.-W. Cho, E. J. Roh, S.-G. Lee, Bull. Kor. Chem. Soc. 2008, 29, 1705 - 1710.
19. J. Sha, J. Liebscher, Synthesis 2008, 917 - 920.
20. a) W. Kantlehner, E. Haug, W. W. Mergen, P. Speh, T. Maier, J. J. Kapassakalidis, H.-J. Bräuner, Synthesis 1983, 904 - 905;
21. b) W. Kantlehner, E. Haug, W. W. Mergen, P. Speh, J. J. Kapassakalidis, H.-J. Bräuner, H. Hagen, Liebigs Ann. Chem. 1984, 108 - 126.
22. T. Isobe, T. Ishikawa, J. Org. Chem. 1999, 64, 6984 - 6988.
23. N. Tamura, Y. Matsushita, T. Iwama, S. Harada, S. Ki-shimoto, K. Itoh, Chem. Pharm. Bull. 1991, 39, 1199 - 1212.
24. J. Alfaro-Lopez, T. Okayama, K. Hosohata, P. Davis, F. Porreca, H. Yamamura, V. J. Hruby, J. Med. Chem. 1999, 42, 5359 - 5368.
25. H. Lecher, F. Graf, Liebigs Ann. Chem. 1924, 438, 154 - 169.
26. a) N. M. M. Mateus, L. C. Branco, M. M. T. Lourenço, C. A. M. Afonso, Green Chem. 2003, 5, 347 - 352;
27. b) P. S. Kulkarni, L. C. Branco, J. G. Crespo, M. C. Nunes, A. Raymundo, C. A. M. Afonso, Chem. Eur. J. 2007, 13, 8478 - 8488.
28. R. B. Homer, K. W. Alwis, J. Chem. Soc., Perkin Trans. 2 1976, 781 - 784.
29. H.-B. König, W. Schröck, K.-G. Metzger, H. Disselkötter, Ger. Offen. DE2104579 (A1), 1972.
30. J. Hine, S. J. Ehrenson, W. H. Brader, J. Am. Chem. Soc. 1956, 78, 2282 - 2284.
31. J. G. Atkinson, D. W. Cillis, R. S. Stuart, Can. J. Chem. 1969, 47, 477 - 479.
32. K. T. Sloan, US 19630326, 1965.
33. a) H. Kessler, D. Leibfritz, Chem. Ber. 1971, 104, 2158 - 2169;
34. b) A. V. Santoro, G. Mickevicius, J. Org. Chem. 1979, 44, 117 - 120.
35. Hexamethylguanidinium ion: a) X. Zhang, R. Bau, J. A. Sheehy, K.O. Christe, J. Fluorine Chem. 1999, 98, 121 - 126;
36. b) A. A. Kolomeitsev, G. Bissky, J. Barten, N. Kalinovich, E. Lork, G.-V. Röschenthaler, Inorg. Chem. 2002, 41, 6118 - 6124;
37. c) G.-V. Röschenthaler, E. Lork, G. Bissky, A. A. Kolomeitsev, Z. Krist. - New Cryst. Struct. 2002, 217, 419 - 420;
38. d) W. Frey, M. Vettel, K. Edelmann, W. Kantlehner, Z. Krist. - New Cryst. Struct. 1998, 213, 77 - 78.
39. For selected other hexa-substituted guanidinium ions, see: e) W. Nakanishi, A. Ogino, M. Kawahata, K. Yamaguchi, T. Ishikawa, Tetrahedron Lett. 2007, 48, 8526 - 8530;
40. f) M. Tanaka, H.-U. Siehl, T. Viefhaus, W. Frey, W. Kantlehner, Z. Naturforsch. 2009, 64b, 765 - 772.
41. A synthesis of the methyl ester of 9 from methyl piperidine-4-carboxylate and N,N-dimethylcarbamoyl chloride has been reported: H. L. Yale, K. Losee, J. Martins, M. Holsing, F. M. Perry, J. Bernstein, J. Am. Chem. Soc. 1953, 75, 1933 - 1942.