Ru/C catalyzed cyclization of linear α,ω-diamines to cyclic amines in water

Tetrahedron

Volumn 66, Issue 6, 2010, Pages 1249-1253

  Gädda, Thomas M ^a   Yu, Xiao Yan ^a   Miyazawa, Akira ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Cyclic amine; Cyclization; Deuteration; Intramolecular; Ring closure; Ru C; Synthesis; Water

Indexed keywords

1,6 DIAMINO HEPTANE; ALPHA, OMEGA DIAMINOALKANE; ALUMINUM; CADAVERINE; DIAMINE DERIVATIVE; PUTRESCINE; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 73649087260     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.025     Document Type: Article

References (32)

1. Challis B.C., and Butler A.R. In: Patai S. (Ed). The Chemistry of the Amino Group (1968), Interscience, London, Great Britain 277-347 Chapter 5
2. Yoshimura N., Moritani I., Shimamura T., and Murahashi S.-I. J. Am. Chem. Soc. 95 (1973) 3038-3039
3. Murahashi S.-I., Kondo K., and Hakata T. Tetrahedron Lett. 23 (1982) 229-232
4. Kindler K., and Matthies D. Chem. Ber. 95 (1962) 1992-1998
5. Nishimoto S., Ohtani B., Yoshikawa T., and Kagiya T. J. Am. Chem. Soc. 105 (1983) 7180-7182
6. Ohtani B., Tsuru S., Nishimoto S., and Kagiya T. J. Org. Chem. 55 (1990) 5551-5553
7. Reichle W.T. J. Catal. 144 (1993) 556-568
8. Radha R.V., Srinivas N., Kulkami S.J., and Raghavan K.V. Ind. J. Chem. 38A (1999) 286-290
9. Khai B.-T., Concilio C., and Porzi G. J. Org. Chem. 46 (1981) 1759-1760
10. Tsuji Y., Shida J., Takeuchi R., and Watanabe Y. Chem. Lett. 13 (1984) 889-890
11. Doctorovich F., and Trapani C. Tetrahedron Lett. 40 (1999) 4635-4638
12. See reviews and references cited therein
13. Müller T.E., and Beller M. Chem. Rev. 98 (1998) 675-703
14. Müller T.E., Hultzsch K.C., Yus M., Fuoeblo F., and Tada M. Chem. Rev. 108 (2008) 3795-3892
15. Stella L. Angew. Chem., Int. Ed. Engl. 22 (1983) 337-350
16. Pugin B., and Venanzi L.M. J. Organomet. Chem. 214 (1981) 125-133
17. Di Martino A., Galli C., Gargano P., and Mandolini L. J. Chem. Soc. Perkin Trans. 2 (1985) 1345-1349
18. De Kimpe N., Boelens M., Piqueur J., and Baele J. Tetrahedron Lett. 35 (1994) 1925-1928
19. De Kimpe N., and De Smaele D. Tetrahedron Lett. 35 (1994) 8023-8026
20. Miyazawa A., Tanaka K., Sakakura T., Tashiro M., Tashiro H., Prakash G.K.S., and Olah G.A. Chem. Commun. (2005) 2104-2106
21. Miyazawa A., Saitou K., Tanaka K., Gädda T.M., Tashiro M., Prakash G.K.S., and Olah G.A. Tetrahedron Lett. 47 (2006) 1437-1439
22. Tyman J.H. J. Appl. Chem. 20 (1970) 179-182
23. Coy J.H., Hegarty A.F., Flynn E.J., and Scott F.L. J. Chem. Soc. Perkin Trans. 2 (1974) 53-58
24. De Angelis F., Grgurina I., and Nicoletti R. Synthesis (1979) 70-71
25. Khai B.-T., Concilio C., and Porzi G. J. Organomet. Chem. 208 (1981) 249-251
26. Arcelli A., Khai B.-T., and Porzi G. J. Organomet. Chem. 235 (1982) 93-96
27. Struve C., and Christophersen C. Heterocycles 69 (2003) 1907-1914
28. Serra M., Salagre P., Cesteros Y., Medina F., and Sueiras J.E. J. Catal. 197 (2001) 210-219
29. Miyazawa A., Tashiro M., Prakash G.K.S., and Olah G.A. Bull. Chem. Soc. Jpn. 79 (2006) 791-792
30. Murahashi S.-I., Yano T., and Hino K. Tetrahedron Lett. 16 (1975) 4235-4238
31. Alexakis E., Hickey M.J., Jones J.R., Kingston L.P., Lockley W.J.S., Mather A.N., Smith T., and Wilkinson D.J. Tetrahedron Lett. 46 (2005) 4291-4293
32. Zacharie B., Moreau N., and Dockendorf C. J. Org. Chem. 66 (2001) 5264-5265