First regioselective iodocyclization of O-allylselenocarbamates

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7764-7768

  Garud, Dinesh R ^a   Makimura, Masaki ^a   Ando, Hiromune ^a   Ishihara, Hideharu ^a   Koketsu, Mamoru ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

1,3 Oxaselenolane; Isoselenocyanate; Selenium; Selenocarbamate

Indexed keywords

ALKYL GROUP; ALLYL COMPOUND; CARBAMIC ACID DERIVATIVE; IMINE; IODINE DERIVATIVE; SELENIUM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DEHYDROHALOGENATION; INFRARED SPECTROSCOPY; ISOMER; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 34848855754     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.040     Document Type: Article

References (36)

1. Ogawa A., and Sonoda N. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 6 (1991), Pergamon Press, Oxford 461
2. Ogawa A., and Sonoda N. Rev. Heteroat. Chem. 10 (1994) 43
3. Guziec Jr. F.S., and Guziec L.J. In: Katritzky A.R., Meth-Cohn O., and Rees C.W. (Eds). Comprehensive Organic Functional Group Transformations Vol. 6 (1995), Pergamon, Oxford 587
4. Dell C.P. In: Katritzky A.R., Meth-Cohn O., and Rees C.W. (Eds). Comprehensive Organic Functional Group Transformations Vol. 5 (1995), Pergamon, Oxford 565
5. Krief A. In: Abel W.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry Vol. 11 (1995), Pergamon, Oxford 515
6. In: Back T.G. (Ed). Organoselenium Chemistry: A Practical Approach (1999), Oxford University Press, Oxford 999
7. Kumar Y., Green R., Borysko K.Z., Wise D.S., Wotring L.L., and Townsend L.B. J. Med. Chem. 36 (1993) 3843
8. Kumar Y., Green R., Wise D.S., Wotring L.L., and Townsend L.B. J. Med. Chem. 36 (1993) 3849
9. Koketsu M., Ishihara H., and Hatsu M. Res. Commun. Mol. Pathol. Pharmacol. 101 (1998) 179
10. Koketsu M., Ishihara H., Wu W., Murakami K., and Saiki I. Eur. J. Pharm. Sci. 9 (1999) 157
11. Wu W., Murakami K., Koketsu M., Yamada Y., and Saiki I. Anticancer Res. 19 (1999) 5375
12. Cho S.I., Koketsu M., Ishihara H., Matsushita M., Nairn A.C., Fukazawa H., and Uehara Y. Biochim. Biophys. Acta. 1475 (2000) 207
13. Du J., Surzhykov S., Lin J.S., Newton M.G., Cheng Y.C., Schinazi R.F., and Chu C.K. J. Med. Chem. 40 (1997) 2991
14. Chu C.K., Ma L., Olgen S., Pierra C., Du J., Gumina G., Gullen E., Cheng Y.C., and Schinazi R.F. J. Med. Chem. 43 (2000) 3906
15. See the review:. Koketsu M., and Ishihara H. Curr. Org. Synth. 3 (2006) 439-455
16. See the review:. Garud D.R., Koketsu M., and Ishihara H. Molecules 12 (2007) 504-535
17. Barton D.H.R., Parekh S.I., Tajbakhsh M., Theodorakis E.A., and Tse C.-L. Tetrahedron 50 (1994) 639-654
18. Bakhsh M.T., Behshtiha Y.S., and Heravi M.M. J. Chem. Soc. Pak. 18 (1996) 159-162
19. Koketsu M., Yamamura Y., and Ishihara H. Heterocycles 68 (2006) 1191-1200
20. Koketsu M., Yamamura Y., Ando H., and Ishihara H. Heterocycles 68 (2006) 1267-1273
21. Koketsu M., Otsuka T., and Ishihara H. Heterocycles 68 (2006) 2107-2112
22. Koketsu M., Sakai T., Kiyokuni T., Garud D.R., Ando H., and Ishihara H. Heterocycles 68 (2006) 1607-1615
23. Koketsu M., Yamamura Y., and Ishihara H. Synthesis (2006) 2738-2742
24. Koketsu M., Takahashi A., and Ishihara H. J. Heterocyclic Chem. 44 (2007) 79-81
25. Koketsu M., Otsuka T., Swenson D., and Ishihara H. Org. Biomol. Chem. 5 (2007) 613-616
26. Only one report from N-dialkyl-O-alkylselenocarbamates has been published recently concerning the synthesis of a 1,3-oxaselenolium salts. See:. Perst H. Sci. Synthesis 11 (2002) 93-95
27. See the review:. Frederickson M., and Grigg R. Org. Prep. Proced. Int. 29 (1997) 33
28. 11NOSe: C, 50.01; H, 4.62; N, 5.83. Found: C, 50.27; H, 4.71, N, 5.90.
29. ++H].
30. Koketsu M., Kiyokuni T., Sakai T., Ando H., and Ishihara H. Chem. Lett. 35 (2006) 626-627
31. 15NOSe: C, 55.72; H, 5.40; N, 5.00. Found: C, 55.57; H, 5.50, N, 4.77.
32. Asanuma Y., Fujiwara S., Shin-ike T., and Kambe N. J. Org. Chem. 69 (2004) 4845-4848
33. Ramazani A., Morsali A., Ganjeie B., Kazemizadeh A.R., and Ahmadi E. Phosphorus, Sulfur Silicon Relat. Elem. 180 (2005) 2439-2442
34. Ramazani A., Kazemizadeh A.R., Ganjeie B., and Ahmadi E. Asian J. Chem. 17 (2005) 2371-2374
35. Ramazani A., Morsali A., Ganjeie B., Kazemizadeh A.R., Ahmadi E., Kempe R., and Hertle I. Z. Naturforsch. 60b (2005) 569-571
36. Koketsu M., Kanoh K., and Ishihara H. Heterocycles 68 (2006) 2627-2633