Gallium iodide/iodine as a versatile reagent for the aza-Prins cyclization: an expeditious synthesis of 4-iodopiperidines

Tetrahedron Letters

Volumn 49, Issue 20, 2008, Pages 3330-3334

  Yadav, J S ^a   Subba Reddy, B V ^a   Chaya, D N ^a   Narayana Kumar, G G K S ^a   Aravind, S ^a   Kunwar, A C ^a   Madavi, C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

4 Iodopiperidine; Aza Prins cyclization; Homoallylic amines; Molecular iodine

Indexed keywords

4 IODO 2 PHENYLPIPERIDINE; 4 IODOPIPERIDINE DERIVATIVE; GALLIUM; IODIDE; IODINE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 41949093836     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.006     Document Type: Article

References (28)

1. Jones T.H., and Blum M.S. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 1 (1983), Wiley, New York 33-84 Chapter 2
2. Fodor G.B., and Colasanti B. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 3 (1985), Wiley, New York 1-90 Chapter 1
3. Schneider M.J. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 10 (1996), Wiley, New York 155-315 Chapter 3
4. Strunz G.M., and Findlay J.A. In: Brossi A. (Ed). The Alkaloids Vol. 26 (1985), Academic, London, UK 89-183 Chapter 3
5. Numata A., and Ibuka I. In: Brossi A. (Ed). The Alkaloids Vol. 31 (1987), Academic, New York 193-315
6. Angle R.S., and Breitenbucher J.G. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry. Stereoselective Synthesis (Part J) Vol. 16 (1995), Elsevier, Amsterdam, The Netherlands 453-502
7. Gershwin M.E., and Terr A. Clin. Rev. Allergy Immunol. 14 (1996) 241
8. Micel K.-H., Sandberg F., Haglid F., and Norin T. Acta. Pharm. Suec. 4 (1967) 97
9. Micel K.-H., Sandberg F., Haglid F., Norin T., Chan R.P.K., and Craig J.C. Acta Chem. Scand. 23 (1969) 3479
10. Laschat S., and Dickner T. Synthesis (2000) 1781-1813
11. Bailey P.D., Millwood P.A., and Smith P.D. Chem. Commun. (1998) 633-640
12. Weintraub P.M., Sabol J.S., Kane J.M., and Borcherding D.R. Tetrahedron 59 (2003) 2953-2989
13. Felpin F.-X., and Lebreton J. Eur. J. Org. Chem. (2003) 3693-3712
14. Couty F. Amino Acids 16 (1999) 297-320 Interscience: New York, 1972; Vol. 2, pp 1-95
15. Carballo R.M., Rami{dotless}rez M.A., Rodri{dotless}guez M.L., Marti{dotless}n V.S., and Padron J.I. Org. Lett. 8 (2006) 3837
16. Dobbs A.P., and Guesne S.J.J. Synlett (2005) 2101-2103
17. Dobbs A.P., Guesne S.J.J., Hursthouse M.B., and Coles S.J. Synlett (2003) 1740-1742
18. Dobbs A.P., Guesne S.J.J., Martinovic S., Coles S.J., and Hursthouse M.B. J. Org. Chem. 68 (2003) 7880-7883
19. Chatani N., Inoue H., Kotsuma T., and Murai S. J. Am. Chem. Soc. 124 (2002) 10294
20. Yamaguchi M., Tsukagoshi T., and Arisawa M. J. Am. Chem. Soc. 121 (1999) 4074
21. Asao N., Asano T., Ohishi T., and Yamamoto Y. J. Am. Chem. Soc. 122 (2000) 4817
22. Yadav J.S., Reddy B.V.S., Eeshwaraiah B., Gupta M.K., and Biswas S.K. Tetrahedron Lett. 46 (2005) 1161
23. Yadav J.S., Reddy B.V.S., Padmavani B., and Gupta M.K. Tetrahedron Lett. 45 (2004) 7577
24. Yadav J.S., Subba Reddy B.V., Narayana Kumar G.G.K.S., and Swamy T. Tetrahedron Lett. 48 (2007) 2205-2208
25. Yadav J.S., Subba Reddy B.V., Narayana Kumar G.G.K.S., and Reddy M.G. Tetrahedron Lett. 48 (2007) 4903-4906
26. Yadav J.S., Kumar N.N., Reddy M.S., and Prasad A.R. Tetrahedron 63 (2007) 2689-2694
27. Yadav J.S., Reddy B.V.S., Maity T., and Narayana Kumar G.G.K.S. Tetrahedron Lett. 48 (2007) 7155-7159
28. ++H) 330.