A facile and practical one-pot 'catch and release' synthesis of substituted guanidines

Tetrahedron Letters

Volumn 50, Issue 36, 2009, Pages 5145-5148

  Wang, Ying ^a   Sauer, Daryl R ^a   Djuric, Stevan W ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; GUANIDINE DERIVATIVE; POLYSTYRENE; RESIN; THIOUREA DERIVATIVE;

ARTICLE; BROMINATION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 67650508282     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.113     Document Type: Article

References (21)

1. Berlinck R.G.S. Fortschr. Chem. Org. Naturst. 66 (1995) 119
2. Mori A., Cohen B.D., and Lowenthal A. Guanidines, Historical, Biological, Biochemical, and Clinical Aspects of the Naturally Occurring Guanidino Compounds (1985), Plenum, New York
3. Berlinck R.G.S. Nat. Prod. Rep. 16 (1999) 339
4. Schneider S.E., Bishop P.A., Salazar M.A., Bishop O.A., and Anslyn E.V. Tetrahedron 54 (1998) 15063
5. Wilson L.J., Klopfenstein S.R., and Li M. Tetrahedron Lett. 40 (1999) 3999-4002
6. Linton B.R., Carr A.J., Orner B.P., and Hamilton A.D. J. Org. Chem. 65 (2000) 1566
7. Wu Y., Hamilton S.K., Wilkinson D.E., and Hamilton G.S. J. Org. Chem. 67 (2002) 7553
8. Poss M.A., Iwanowicz E., Reid J.A., Lin J., and Gu Z. Tetrahedron Lett. 33 (1992) 5933
9. Sandin H., Swanstein M., and Wellner E. J. Org. Chem. 69 (2004) 1571
10. Rasmussen C.R., Villani Jr. F.J., Reynolds B.E., Plampin J.N., Hood A.R., Hecker L.R., Nortey S.O., Hanslin A., Costanzo M.J., Howse Jr. R.M., and Molinari A.J. Synthesis 6 (1988) 460
11. Dodd D.S., and Wallace O.B. Tetrahedron Lett. 39 (1998) 5701
12. Ghosh A.K., Hol W.J., and Fan E. J. Org. Chem. 66 (2001) 2161-2164
13. Kilburn J.P., Lau J., and Jones R.C.F. Tetrahedron 58 (2002) 1739-1743
14. Drewry D.H., Gerritz S.W., and Linn J.A. Tetrahedron Lett. 38 (1997) 3377-3380
15. Kearney P.C., Fernandez M., and Flygare J.A. Tetrahedron Lett. 39 (1998) 2663-2666
16. For some recent 'catch and release' examples, see:. Strohmeier G.A., and Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 621-624
17. Porcheddu A., Giampaolo G., De Luca L., and Ruda A.M. J. Comb. Chem. 6 (2004) 105-111
18. Larsen S.D., Stachew C.F., Clare P.M., Cubbage J.W., and Leach K.L. Bioorg. Med. Chem. Lett. 13 (2003) 3491-3495
19. Marugg J.L., Neitzel M.L., and Tucker J. Tetrahedron Lett. 44 (2003) 7537-7540
20. Adams G.L., Graybill T.L., Sanchez R.M., Maggaard V.W., Burton G., and Rivero R.A. Tetrahedron Lett. 44 (2003) 5041-5045
21. 13C-GELMAS experiments. See Supplementary data for details.