Synthesis of polyamino nitriles, en route to acylpolyamine neurotoxins, via the regioselective michael cyanoethylation of unprotected polyamines. Unusual behaviour of 1-(2-aminoethyl)piperazine

Tetrahedron

Volumn 65, Issue 42, 2009, Pages 8727-8732

  Bałczewski, Piotr ^a   Zurawiński, Remigiusz ^a   Mikina, Maciej ^a   Dudziński, Bogdan ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

Acrylonitrile; Addition reactions; Heterocycles; HPLC; Michael cyanoethylation; Polyamines; Polyamino nitriles

Indexed keywords

1 (2 AMINOETHYL)PIPERAZINE; 4,4' METHYLENEBIS(CYCLOHEXYLAMINE); ALIPHATIC AMINE; BIS(3 AMINOPROPYLAMINE)AMINE; CYCLOHEXYLAMINE DERIVATIVE; DIAMINE DERIVATIVE; NEUROTOXIN; NITRILE; PIPERAZINE DERIVATIVE; POLYAMINE; PROPYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; THERMAL ANALYSIS;

EID: 69949120988     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.034     Document Type: Article

References (26)

1. Leeuwenhoek v.A. Phil. Trans. Royal Soc. London 12 (1678) 1040-1043
2. Karigiannis G., and Papaioannou D. Eur. J. Org. Chem. (2000) 1841-1863
3. Totev T., and Glavchev I. J. Univ. of Chem. Technol. and Metal. 40 (2005) 205-208
4. Short F.W., Elslager E.F., Moore A.M., Sullivan M.J., and Tendick F.H. J. Org. Chem. 80 (1958) 223-228
5. Tarbell D.S., Shakespeare N., Claus C.J., and Bunnett J.F. J. Am. Chem. Soc. 68 (1946) 1217-1219
6. Garrett S.W., Davies O.R., Milroy D.A., Wood P.J., Pouton C.W., and Threadgrill M.D. Bioorg. Med. Chem. 8 (2000) 1779-1794
7. Osvath P., Curtis N.F., and Weatherburn D.C. Aust. J. Chem. (1987) 347-360
8. Bueno G.J., Klimkait T., Gilbert I.H., and Simons C. Bioorg. Med. Chem. 11 (2003) 87-94
9. Sata N.U., Sugano M., Matsunaga S., and Fusetani N. Tetrahedron Lett. 40 (1999) 719-722
10. Somin I.N. Zh. Org. Khim. (1968) 128-133
11. J. Org. Chem. USSR (Engl. Transl.) (1968) 122-125
12. Edwards M.L., Stemerick D.M., Bitonti A.J., Dumont J.A., Cann Mc P.P., Bey P., and Sjocrdsma A. J. Med. Chem. 34 (1991) 569-574
13. Edwards M.L., Prakash N.J., Stemerick D.M., Sunkara S.P., Bitonti A.J., Davis G.F., Dumont J.A., and Bey P. J. Med. Chem. 33 (1990) 1369-1375
14. Israel M., Rosenfield J.S., and Modest E.J. J. Med. Chem. 7 (1964) 710-716
15. Onuki H., Ito K., Kobayashi Y., Matsumori N., and Tachibana K. J. Org. Chem. 63 (1998) 3925-3932
16. Frydman B., Bhattacharya S., Sarkar S., Sarkar A., Drandarov K., Chesnov S., Guggisberg A., Popaj K., Sergeyev S., Yurdakul A., Hesse M., Basu H., and Marton L.J. J. Med. Chem. 4 (2004) 1051-1059
17. Kaderabek V., and Kalfus K. Collect. Czech. Chem. Commun. 41 (1976) 433-442
18. Lee Y.B., Park M.H., and Folk J.E. J. Med. Chem. 38 (1995) 3053-3061
19. Lawrance G.A., Martinez M., Skelton B.W., and White A.H. J. Chem. Soc., Dalton Trans. 10 (1992) 1649-1652
20. Nishimaru T., Sano M., Yamaguchi Y., and Wakamiya T. Bioorg. Med. Chem. 17 (2009) 57-63
21. Strømgaard K., Andersen K., Krogsgaard-Larsen P., and Jaroszewski J.W. Mini-Rev. Med. Chem. 1 (2001) 317-338
22. Olsen C.A., Witt M., Jaroszewski J.W., and Franzyk H. Org. Lett. 5 (2003) 4183-4185
23. For a health hazards data see: http://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS &p_id=10066.
24. Zagidullin R.N. Zh. Obshch. Khim. 61 (1991) 247-253
25. Zagidullin R.N. Khim. Geterotsik. Soed. 3 (1991) 381-385
26. Chem. Heterocycl. Compd 27 (1991) 309-312 (Engl. Transl.)