Unexpected regioselectivity in cycloisomerization of 2-alkynyl-3-nitro- thiophenes

Synlett

Volumn , Issue 20, 2010, Pages 3027-3030

  Cikotiene, Inga ^a   Sazinas, Rokas ^a   Mazeikaite, Rita ^b   Labanauskas, Linas ^b  

^a VILNIUS UNIVERSITY   (Lithuania)

^b CENTER FOR PHYSICAL SCIENCES AND TECHNOLOGY   (Lithuania)

Author keywords

2 alkynyl 3 nitrothiophenes; catalysis; cycloizomerization; thieno 3,2 c isoxazoles

Indexed keywords

2 ALKYNYL 3 NITROTHIOPHENE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; CYCLIZATION; ISOMERIZATION; OXIDATION; REDUCTION; ROOM TEMPERATURE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 78650175307     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259053     Document Type: Article

References (53)

1. Cacchi S, Fabrizi G, Moro L, Tetrahedron Lett. 1998 39 5101; and references cited therein
2. Chaudhuri G, Chowdhury C, Kundu N G., Synlett 1998 1273
3. Montiero N, Balme G, Synlett 1998 746
4. Chowdhury C, Chaudhuri G, Guha S, Mukherjee A K., Kundu N G., J. Org. Chem. 1998 63 1863
5. Cacchi S, Fabrizi G, Moro L, J. Org. Chem. 1997 62 5327
6. Khan M W., Kundu N G., Synlett 1997 1435
7. Cacchi S, Fabrizi G, Marinelli F, Moro L, Pace P, Synlett 1997 1363
8. Arcadi A, Cacchi S, DelRosario M, Fabrizi G, Marinelli F, J. Org. Chem. 1996 61 9280
9. Chowdhury C, Kundu N G., Chem. Commun. 1996 1067
10. Kundu N G., Pal M, J. Chem. Soc., Chem. Commun. 1993 86
11. Candiani I, DeBernardinis S, Cabri W, Marchi M, Bedeschi A, Penco S, Synlett 1993 269
12. Zhang H, Brumfield K K., Jaroskova L, Maryanoff B E., Tetrahedron Lett. 1998 39 4449
13. Fancelli D, Fagnola M C., Severino D, Bedeschi A, Tetrahedron Lett. 1997 38 2311
14. Fagnola M C., Candiani I, Visentin G, Cabri W, Zarini F, Mongelli N, Bedeschi A, Tetrahedron Lett. 1997 38 2307
15. Gabriele B, Salerno G, Fazio A, Bossio M, Tetrahedron Lett. 2001 42 1339
16. Monteiro N, Arnold A, Balme G, Synlett 1998 1111
17. Larock R C., Pace P, Yang H, Russell C E., Tetrahedron 1998 54 9961
18. Cacchi S, Fabrizi G, Moro L, Synlett 1998 741
19. Cacchi S, Fabrizi G, Moro L, J. Org. Chem. 1997 62 527; and references cited therein
20. Balme G, Bouyssi D, Tetrahedron 1994 50 403
21. Takeda A, Kamijo S, Yamamoto Y, J. Am. Chem. Soc. 2000 122 5662
22. Gabriele B, Salerno G, Fazio A, Org. Lett. 2000 2 351
23. Arcadi A, Cacchi S, DelRosario M, Fabrizi G, Marinelli F, J. Org. Chem. 1996 61 9280
24. Cacchi S, Fabrizi G, Moro L, Tetrahedron Lett. 1998 39 5101
25. Roesh K R., Larock R C., Org. Lett. 1999 1 553
26. Roesh K R., Larock R C., J. Org. Chem. 2002 67 86
27. Dai G, Larock R C., Org. Lett. 2001 3 4035
28. Dai G, Larock R C., Org. Lett. 2002 4 193
29. Zhang H, Larock R C., J. Org. Chem. 2002 67 7048
30. Yue D, DellaCa N, Larock R C., Org. Lett. 2004 1581
31. Yue D, DellaCa N, Larock R C., [nl]J. Org. Chem. 2005 3381
32. Pfeiffer P, Justus Liebigs Ann.Chem. 1916 411 72
33. Bond C C., Hooper M, J. Chem. Soc. 1969 2453
34. Price D W., Dirk S M., Maya F, Tour J M., Tetrahedron 2003 59 2497
35. Ruggli C, Helv. Chim. Acta 1944 27 649
36. Nepveu F, Kim S, Boyer J, Ibrahim H, Reybier K, Monje M.-C, Chevalley S, Perio P, Lajoie B H., Bouajila J, Deharo E, Sauvain M, Valentin A, Chatriant O, Petit S, Nallet J.-P, Tahar R, Basco L, Pantaleo A, Turini F, Arese P, Thompson E, Vivas L, J. Med. Chem. 2010 53 699
37. Adams D B., Hooper M, Morpeth A G., Raper E S., Clegg W, Stoddart B, J. Chem. Soc., Perkin Trans. 2 1990 1269
38. Baeyer A, Ber. Dtsch. Chem. Ges. 1881 14 1741
39. Baeyer A, Ber. Dtsch. Chem. Ges. 1882 15 775
40. Pfeiffer P, Ber. Dtsch. Chem. Ges. 1912 45 1819
41. Pfeiffer P, Kramer E, Ber. Dtsch. Chem. Ges. 1913 46 3655
42. Abromovich R A., Cue B W., J. Org. Chem. 1980 45 5316
43. Asao N, Sato K, Yamamoto Y, Tetrahedron Lett. 2003 44 5675
44. Soderberg B C. G., Gorugantula S P., Howerton C R., Petersen J L., Dantale S W., Tetrahedron 2009 65 7357
45. Susvilo I, Brukstus A, Tumkevicius S, Synlett 2003 1151
46. Cikotiene I, Pudziuvelyte E, Brukstus A, Tumkevicius S, Tetrahedron 2007 63 8145
47. Cikotiene I, Pudziuvelyte E, Brukstus A, J. Heterocycl. Chem. 2008 45 1615
48. Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett. 1975 16 4467
49. Carpanelli L, Ann. Chim. (Rome) 1961 51 181
50. Steinkopf W, Jacob H, Penz H, Justus Liebigs Ann. Chem. 1934 512 136
51. Altomare A, Burla M C., Camalli M, Cascarano G L., Giacovazzo C, Guagliardi A, Moliterni A G. G., Spagna R, J. Appl. Crystallogr. 1999 115
52. Sheldrick G M., SHELXL97, Program for the Refinement of Crystal Structures University of Göttingen Germany 1997
53. Johnson C K., ORTEP-II, Report ORNL-5138 Oak Ridge National Laboratory Oak Ridge TN 1976