On the photoreaction of some 1,2,4-oxadiazoles in the presence of 2,3-dimethyl-2-butene. Synthesis of N-imidoyl-aziridines

Heterocycles

Volumn 71, Issue 7, 2007, Pages 1529-1537

  Palumbo Piccionello, Antonio ^a   Pibiri, Ivana ^a   Pace, Andrea ^a   Raccuglia, Rosa Angela ^a   Buscemi, Silvestre ^a   Vivona, Nicolò ^a   Giorgi, Gianluca ^b  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

1,2,4 Oxadiazo; N Allylamidin; N Imidoylaziridin; Photochemistry; Pyrolysi

Indexed keywords

EID: 40949137410     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-07-11040     Document Type: Article

References (56)

1. Diana G.D., Volkots D.L., Nitz T.J., Bailey T.R., Long M.A., Vescio N., Aldous S., Pevear D.C., and Dutko F.J. J. Med. Chem. 37 (1994) 2421
2. Saunders J., Cassidy M., Freedman S.B., Harley E.A., Iversen L.L., Kneen C., MacLeod A.M., Merchant K.J., Snow R.J., and Baker R. J. Med. Chem. 33 (1990) 1128
3. Borzilleri R.M., Zheng X., Qian L., Ellis C., -wei Cai Z., Wautlet B.S., Mortillo S., Jeyaseelan Sr. R., Kukral D.W., Fura A., Kamath A., Vyas V., Tokarski J.S., Barrish J.C., Hunt J.T., Lombardo L.J., Fargnoli J., and Bhide R.S. J. Med. Chem. 48 (2005) 3991
4. Macor J.E., Ordway T., Smith R.L., Verhoest P.R., and Mack R.A. J. Org. Chem. 61 (1996) 3228
5. Gur E., Dremencov E., Lerer B., and Newman M.E. Eur. J. Pharmacol. 411 (2001) 115
6. Watson J., Selkirk J.V., and Brown A.M. J. Biomol. Screening 3 (1998) 101
7. Pauwels P.J., Wurch T., Palmier C., and Br. Colpaert F.C. J. Pharmacol. 123 (1998) 51
8. Naka T., and Kubo K. Curr. Pharm. Des. 5 (1999) 453
9. Pibiri I., Pace A., Palumbo Piccionello A., Pierro P., and Buscemi S. Heterocycles 68 (2006) 2653
10. Torgova S.I., Karamysheva L.A., Geivandova T.A., and Strigazzi A. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A: Mol. Cryst. Liq. Cryst. 365 (2001) 1055
11. Taguchi T. Jpn. Kokai Tokkyo Koho 2000096043 (2000)
12. Buscemi S., Cicero M.G., Vivona N., and Caronna T. J. Chem. Soc., Perkin Trans. 1 (1988) 1313
13. Buscemi S., Cicero M.G., Vivona N., and Caronna T. J. Heterocycl. Chem. 25 (1988) 931
14. Buscemi S., Pace A., Pibiri I., and Vivona N. J. Org. Chem. 67 (2002) 6253
15. Pace A., Pibiri I., Buscemi S., Vivona N., and Malpezzi L. J. Org. Chem. 69 (2004) 4108
16. Pace A., Buscemi S., and Vivona N. J. Org. Chem. 70 (2005) 2322
17. Buscemi S., and Vivona N. J. Heterocycl. Chem. 25 (1988) 1551
18. Buscemi S., Vivona N., and Caronna T. J. Org. Chem. 61 (1996) 8397
19. Buscemi S., Cusmano G., and Gruttadauria M. J. Heterocycl. Chem. 27 (1990) 861
20. Buscemi S., and Vivona N. Heterocycles 29 (1989) 737
21. Buscemi S., Macaluso G., and Vivona N. Heterocycles 29 (1989) 1301
22. Buscemi S., and Vivona N. J. Chem. Soc., Perkin Trans. 2 (1991) 187
23. Buscemi S., Pace A., Palumbo Piccionello A., Pibiri I., and Vivona N. Heterocycles 63 (2004) 1619
24. Buscemi S., Pace A., Palumbo Piccionello A., Pibiri I., and Vivona N. Heterocycles 65 (2005) 387
25. Vivona N., Buscemi S., Asta S., and Caronna T. Tetrahedron 53 (1997) 12629
26. Weissberger A., and Taylor E.C. The Chemistry of Heterocyclic Compounds: Small Rings Heterocycles 42 (1983), Wiley For recent applications, see for example:
27. Zhdankin V.V., and Stang J.P. Chem. Rev. 102 (2002) 2523
28. Ando T., Minakata S., Ryu I., and Komatsu M. Tetrahedron Lett. 39 (1998) 309
29. Albone D.P., Aujla P.S., Taylor P.C., Challenger S., and Derrick A.M. J. Org. Chem. 63 (1998) 9569
30. Jeong J.U., Tao B., Sagasser I., Henniges H., and Sharpless K.B. J. Am. Chem. Soc. 120 (1998) 6844
31. Dauban P., and Dodd R.H. Tetrahedron Lett. 42 (2001) 1037
32. Evans D.A., Faul M.M., and Bilodeau M.J. J. Am. Chem. Soc. 116 (1994) 2742
33. Duran F., Leman L., Ghini A., Burton G., Dauban P., and Dodd R.H. Org. Lett. 4 (2002) 281
34. Chenna P.H.D., Dauban P., Ghini A., Burton G., and Dodd R.H. Tetrahedron Lett. 41 (2000) 7041
35. Müller P. Transition Metal-Catalyzed Nitrene Transfer. In: Doyle M.P. (Ed). Advances in Catalytic Processes (1997), JAI Press, Greenwich, CT
36. Evans D.A., Faul M.M., and Bilodeau M.T. J. Org. Chem. 56 (1991) 6744
37. Lebel H., Huard K., and Lectard S. J. Am. Chem. Soc. 127 (2005) 14198
38. Padwa A., Flick A.C., Leverett C.A., and Stengel T. J. Org. Chem. 69 (2004) 6377
39. Leca D., Toussaint A., Mareau C., Fensterbank L., Lacôte E., and Malacria M. Org. Lett. 6 (2004) 3573
40. Buscemi S., Pace A., Vivona N., Caronna T., and Galia A. J. Org. Chem. 64 (1999) 7028
41. Calculated according to the Rehm-Weller equation. Rehm D., and Weller A. Isr. J. Chem. 8 (1970) 259
42. An IP value of 1.54 V vs SCE was used for 2,3-dimethyl-2-butene.
43. McCullough J.J., Miller R.C., Fung D., and Wu W.S. J. Am. Chem. Soc. 97 (1975) 5942
44. Kashelikar D.V., and Fanta P.E. J. Org. Chem. 82 (1960) 4930
45. Kalvins I., Adrianov V., Shestakova I., Kanepe I., and Domracheva I. Chem. Abstr. 134 (2001) 252268 PCT Int. Appl. WO 2001021585, 2001
46. Semenii V.Y., Solodushchenko G.F., and Kutovoi A.I. Chem. Abstr. 105 (1986) 165002 SU Patent No. 1004397, 1985
47. Murai N., Komatsu M., Yagii T., Nishihara H., Ohshiro Y., and Agawa T. J. Org. Chem. 42 (1977) 847
48. Heine H.W., and Bender H.S. J. Org. Chem. 25 (1959) 461
49. Heinz P., Mechthild H., and Margit R. Chem. Abstr. 99 (1983) 175767 DD Patent No: 200619, 1983
50. Rudorf W.D. Tetrahedron 36 (1980) 179
51. Johnson J.J., Nwoko D., Hotema M., Sanchez N., Alderman R., and Lynch V. J. Heterocycl. Chem. 33 (1996) 1583
52. Baek G.U., and Lee B. Chem. Abstr. 137 (2002) 232642 KR Patent No. 2000067156, 2000
53. Sim Ooi N., and Wilson D.A. J. Chem. Soc., Perkin Trans. 2 (1980) 1792
54. Polya J.B., and Spotswood T.M. Rec. Trav. Chim. 67 (1948) 927
55. Sheldrick G.M. SHELXS-97, Rel. 97-2, A program for automatic solution of crystal structures (1997), Göttingen University
56. Sheldrick G.M. SHELXL-97, Rel. 97-2, A program for crystal structure refinement (1997), Göttingen University