A new route to thiopyran S,S-dioxide derivatives via an overall ring-enlargement protocol from 3-nitrothiophene

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 336-343

  Bianchi, Lara ^a   Maccagno, Massimo ^a   Petrillo, Giovanni ^a   Rizzato, Egon ^b   Sancassan, Fernando ^a   Severi, Elda ^a   Spinelli, Domenico ^b   Stenta, Marco ^b   Galatini, Andrea ^a   Tavani, Cinzia ^a  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

3 Nitrothiophene; Ring expansion; Ring enlargement protocol; Ring opening ring closing reactions; Sulfur heterocycles; Thiopyran S,S dioxides

Indexed keywords

3 (4 CHLOROPHENYL) 4 NITRO 3,6 DIHYDRO 2H THIOPYRAN 1,1 DIOXIDE; 3 (4 METHOXYPHENYL) 4 NITRO 3,6 DIHYDRO 2H THIOPYRAN 1,1 DIOXIDE; 4 METHANESULFONYL 2 NITRO 1,3 BUTADIENYL] 4 METHOXYBENZENE; 4 METHANESULFONYL 2 NITRO 1,3 BUTADIENYL]BENZENE; 4 NITRO 3 (2 METHYLPHENYL) 3,6 DIHYDRO 2H THIOPYRAN 1,1 DIOXIDE; 4 NITRO 3 (3 METHYLPHENYL) 3,6 DIHYDRO 2H THIOPYRAN 1,1 DIOXIDE; 4 NITRO 3 (4 METHYLPHENYL) 3,6 DIHYDRO 2H THIOPYRAN 1,1 DIOXIDE; 4 NITRO 3 PHENYL 3,6 DIHYDRO 2H THIOPYRAN 1,1 DIOXIDE; BENZENE DERIVATIVE; OXIDE; THIOPHENE DERIVATIVE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG STRUCTURE; PRIORITY JOURNAL; RING CLOSING METATHESIS; RING OPENING;

EID: 85040693542     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.046     Document Type: Article

References (49)

1. Bianchi L., Dell'Erba C., Maccagno M., Morganti S., Novi M., Petrillo G., Rizzato E., Sancassan F., Severi E., Spinelli D., and Tavani C. Tetrahedron 60 (2004) 4967-4973
2. Saito T., Horikoshi T., Otani T., Matsuda Y., and Karakasa T. Tetrahedron Lett. 44 (2003) 6513-6517
3. Katritzky A.R., and Button M.A.C. J. Org. Chem. 66 (2001) 5595-5600
4. Ram V.J., Srivastava P., and Saxena A.S. J. Org. Chem. 66 (2001) 5333-5337
5. Hori M., Kataoka T., Shimizu H., Imai E., Iwata N., Kawamura N., Kurono M., Nakano K., and Kido M. Chem. Pharm. Bull. 37 (1989) 1282-1286
6. Ingall A.H. In: Boulton A.J., and McKillop A. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon, Oxford 885-942
7. Ingall A.H. In: McKillop A. (Ed). Comprehensive Heterocyclic Chemistry II Vol. 5 (1996), Pergamon, Oxford 501
8. Van Vliet L.A., Rodenhuis N., Dijkstra D., Wikstroem H., Pugsley T.A., Serpa K.A., Meltzer L.T., Heffner T.G., Wise L.D., Lajiness M.E., Huff R.M., Svensson K., Sundell S., and Lundmark M. J. Med. Chem. 43 (2000) 2871-2882
9. Baurmgarth M., Beier N., and Gericke R. J. Med. Chem. 41 (1998) 3736-3747
10. Al-Nakib T., Bezjak V., Rashid S., Fullam B., and Meegan M.J. Eur. J. Med. Chem. 26 (1991) 221-230
11. Al-Nakib T., Bezjak V., Meegan M.J., and Chandy R. Eur. J. Med. Chem. 25 (1990) 455-457
12. Pigini M., Brasili L., Giannella M., Giardinà D., Gulini U., Quaglia W., and Melchiorre C. J. Med. Chem. 31 (1988) 2300-2304
13. Holshouser M.H., and Loeffler L.J. J. Pharm. Sci. 71 (1982) 715-717
14. Holshouser M.H., Loeffler L.J., and Hill I.H. J. Med. Chem. 24 (1981) 853-858
15. Philip A., Jirkovsky I., and Martel R.R. J. Med. Chem. 23 (1980) 1372-1376
16. Ramalingam K., Thyvelikakath G.X., Berlin K.D., Chesnut R.W., Brown R.A., Durham N.N., Ealick S.E., and van der Helm D. J. Med. Chem. 20 (1977) 647-650
17. For less recent reports on the pharmacological (antipyretic, antidepressant and analgesic) properties of thiochromans see:. Adv. Heterocycl. Chem. 18 (1975) 59-97
18. Abaee M.S., Mojtahedi M.M., Zahedi M.M., Sharifi R., and Khavasi H. Synthesis 21 (2007) 3339-3344
19. Rosiak A., Frey W., and Christoffers J. Eur. J. Org. Chem. (2006) 4044-4054
20. Rosiak A., and Christoffers J. Tetrahedron Lett. 47 (2006) 5095-5097
21. Oh K., Kim H., Cardelli F., Bwititi M., and Martynow A.M. J. Org. Chem. 73 (2008) 2432-2434 and references cited therein
22. Vedejs E., Galante R., and Gioekjian P. J. Am. Chem. Soc. 120 (1998) 3613-3622
23. Jheengut V., and Ward D.E. J. Org. Chem. 72 (2007) 7805-7808
24. Jayabharathi J., Thanikachalam V., Thangamani A., and Padmavathy M. Med. Chem. Res. 16 (2007) 266-279
25. Hollick J.J., Rigoreau L.J.M., Cano-Soumullac C., Cockcroft X., Curtin N.J., Frigerio M., Golding B.T., Guiard S., Hardcastle J.R., Hickson I., Hummersone M.G., Menear K.A., Martin N.M.B., Matthews I., Newell D.R., Ord R., Richardson C.J., Smith G.C.M., and Griffin R.J. J. Med. Chem. 50 (2007) 1958-1972
26. Bianchi L., Maccagno M., Petrillo G., Rizzato E., Sancassan F., Severi E., Spinelli D., Tavani C., and Viale M. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems: Chemistry and Properties Vol. 11 (2007), Società Chimica Italiana, Roma 1-20
27. Bianchi L., Maccagno M., Petrillo G., Sancassan F., Spinelli D., and Tavani C. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems: Chemistry and Properties Vol. 10 (2006), Società Chimica Italiana, Roma 1-23
28. Bianchi L., Dell'Erba C., Maccagno M., Morganti S., Petrillo G., Rizzato E., Sancassan F., Severi E., Spinelli D., and Tavani C. Arkivoc vii (2006) 169-185
29. Dell'Erba C., Novi M., Petrillo G., and Tavani C. In: Attanasi O.A., and Spinelli D. (Eds). Topics in Heterocyclic Systems: Synthesis, Reactions and Properties Vol. 1 (1996), Research Signpost, Trivandrum, India 1-12
30. Spinelli D., Consiglio G., Dell'Erba C., and Novi M. In: Gronowitz S. (Ed). The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives Vol. 44 (1991), John Wiley & Sons, New York, NY 295-396
31. Dell'Erba C., Gabellini A., Novi M., Petrillo G., Tavani C., Cosimelli B., and Spinelli D. Tetrahedron 57 (2001) 8159-8165
32. Bianchi L., Dell'Erba C., Maccagno M., Petrillo G., Rizzato E., Sancassan F., Severi E., and Tavani C. J. Org. Chem. 70 (2005) 8734-8738
33. Nielsen A.T. Nitronic Acids and Esters. In: Feuer H. (Ed). The Chemistry of the Nitro and Nitroso Groups (1969), Interscience, New York, NY Chapter 7
34. Frisch, M. J. et al. Gaussian 98. See Supplementary data for full citation.
35. Geerlings P., De Proft F., and Langenaeker W. Chem. Rev. 103 (2003) 1793-1873
36. Frisch, M. J. et al. Gaussian 03, Revision C.02. See Supplementary data for full citation.
37. Barone V., Cossi M., and Tomasi J. J. Comput. Chem. 19 (1998) 404-417
38. Barone V., and Cossi M. J. Phys. Chem. A 102 (1998) 1995-2001
39. Becke A.D. Phys. Rev. A 38 (1988) 3098-3100
40. Becke A.D. J. Chem. Phys. 98 (1993) 1372-1377
41. Substituent constant values from Exner, O. Correlation Analysis of Chemical Data (1988), Plenum, New York, NY, London pp 61-62, 143-144
42. Kabalka G.W., and Goudgaon N.M. Synth. Commun. 18 (1988) 693-697
43. Ballini R., and Petrini M. J. Chem. Soc., Perkin Trans. 1 (1988) 2563-2565
44. Carosati E., Cruciani G., Chiarini A., Budriesi R., Ioan P., Spisani R., Spinelli D., Cosimelli B., Fusi F., Frosini M., Matucci R., Gasparrini F., Ciogli A., Stephens P.J., and Devlin F.J. J. Med. Chem. 49 (2006) 5206-5216
45. Coburn R.A., Wierzba M., Suto M.J., Solo A.J., Triggle A.M., and Triggle D.J. J. Med. Chem. 31 (1988) 2103-2107
46. Viale M., Petrillo G., Maccagno M., Castagnola P., Aiello C., Cordazzo C., Mariggiò M.A., Jadhav S.A., Bianchi L., Leto G., Rizzato E., Poggi A., and Spinelli D. Eur. J. Pharmacol. 588 (2008) 47-51
47. Petrillo G., Mariggiò M.A., Aiello C., Cordazzo C., Fenoglio C., Morganti S., Croce M., Rizzato E., Spinelli D., Maccagno M., Bianchi L., Prevosto C., Tavani C., and Viale M. Bioorg. Med. Chem. 16 (2008) 240-247
48. Fenoglio C., Grosso A., Petrillo G., Boncompagni E., Aiello C., Cordazzo C., Spinelli D., Ognio E., Mariggiò M.A., Cassano A., and Viale M. Anticancer Res. 28 (2008) 813-824
49. Bergbreit D.E., and Pendergrass E. J. Org. Chem. 46 (1981) 219-220