Easy access to 4-nitrothiochroman S,S-dioxides via ring-enlargement from 3-nitrobenzo[b]thiophene

Tetrahedron

Volumn 60, Issue 23, 2004, Pages 4967-4973

  Bianchi, Lara ^a   Dell'Erba, Carlo ^a   Maccagno, Massimo ^a   Morganti, Stefano ^b   Novi, Marino ^a   Petrillo, Giovanni ^a   Rizzato, Egon ^b   Sancassan, Fernando ^a   Severi, Elda ^a   Spinelli, Domenico ^b   Tavani, Cinzia ^a  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

3 Nitrobenzo b thiophene; Conformations; Nitrothiophenes; Ring enlargement; Ring opening ring closure reactions; Thiochromans

Indexed keywords

3 NITROBENZO[B]THIOPHENE; 4 NITROTHIOCHROMAN; AMIDE; AMMONIUM CHLORIDE; LITHIUM (TRIMETHYLSILYL)AMIDE; OXIDE; SULFIDE; SULFUR; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; METALLATION; MICHAEL ADDITION; MOLECULE; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 2442478527     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.039     Document Type: Article

References (35)

1. Synthetic Exploitation of the Ring-Opening of Nitrothiophenes, Part XVI. For part XV, see Ref. 11
2. Saito T., Horikoshi T., Otani T., Matsuda Y., Karakasa T. Tetrahedron Lett. 44:2003;6513-6517
3. Katritzky A.R., Button M.A.C. J. Org. Chem. 66:2001;5595-5600
4. Ram V.J., Srivastava P., 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., Kido M. Chem. Pharm. Bull. 37:1989;1282-1286
6. Ingall A.H. Boulton A.J., McKillop A. Comprehensive Heterocyclic Chemistry. Vol. 3:1984;885-942 Pergamon, Oxford
7. Ingall A.H. McKillop A. Comprehensive Heterocyclic Chemistry II. Vol. 5:1996;501 Pergamon, Oxford
8. Al-Nakib T., Bezjak V., Rashid S., Fullam B., Meegan M.J. Eur. J. Med. Chem. 26:1991;221-230
9. Al-Nakib T., Bezjak V., Meegan M.J., Chandy R. Eur. J. Med. Chem. 25:1990;455-457
10. 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., Lundmark M. J. Med. Chem. 43:2000;2871-2882
11. Pigini M., Brasili L., Giannella M., Giardinà D., Gulini U., Quaglia W., Melchiorre C. J. Med. Chem. 31:1988;2300-2304
12. Baurmgarth M., Beier N., Gericke R. J. Med. Chem. 41:1998;3736-3747
13. Philip A., Jirkovsky I., Martel R.R. J. Med. Chem. 23:1980;1372-1376
14. Ramalingam K., Thyvelikakath G.X., Berlin K.D., Chesnut R.W., Brown R.A., Durham N.N., Ealick S.E., van der Helm D. J. Med. Chem. 20:1977;647-650
15. Holshouser M.H., Loeffler L.J., Hill I.H. J. Med. Chem. 24:1981;853-858
16. Holshouser M.H., Loeffler L.J. J. Pharm. Sci. 71:1982;715-717
17. (j) For less recent reports on the pharmacological (antipyretic, antidepressant and analgesic) properties of thiochromans see: Adv. Heterocycl. Chem. 1975, 18, 59-97.
18. Brogden P.J., Gabbutt C.D., Hepworth J.D. Boulton A.J., McKillop A. Comprehensive Heterocyclic Chemistry. Vol. 3:1984;573-883 Pergamon, Oxford
19. Miyazaki H., Honda K., Asami M., Inoue S. J. Org. Chem. 64:1999;9507-9511
20. Yadav J.S., Reddy B.V.S., Rao C.V., Rao K.V. J. Chem. Soc., Perkin Trans. 1. 2002;1401-1404
21. Tilak B.D., Vaidya V.M. Tetrahedron Lett. 8:1963;487-495
22. Takido T., Tagagi Y., Itabashi K. J. Heterocycl. Chem. 32:1995;687-690
23. Meyers C.Y., Rinaldi C., Bonoli L. J. Org. Chem. 28:1963;2440-2442
24. Funicello M., Spagnolo P., Zanirato P. J. Chem. Soc., Perkin Trans. 1. 1990;2971-2978
25. Cabiddu M.G., Cabiddu S., Cadoni E., Demurtas P., Fattuoni C., Floris C., Melis S. Synthesis. 1998;1098-1100
26. Bianchi L., Dell'Erba C., Maccagno M., Mugnoli A., Novi M., Petrillo G., Sancassan F., Tavani C. J. Org. Chem. 68:2003;5254-5260. and previous papers in the series
27. Dell'Erba C., Gabellini A., Novi M., Petrillo G., Tavani C., Cosimelli B., Spinelli D. Tetrahedron. 57:2001;8159-8165
28. Bolger B.J., Hirwe A., Marathe K.G., Philbin E.M., Vickars M.A., Lillya C.P. Tetrahedron. 22:1966;621-628
29. Clark-Lewis J.W. Aust. J. Chem. 21:1968;2059-2075
30. Katekar G.F. Aust. J. Chem. 19:1966;1251-1257
31. PC Model Version 7.0 Serena Software, Box 3076, Bloomington, In, USA, 1998.
32. Karplus M. J. Chem. Phys. 30:1959;11-18
33. Conroy H.H. Adv. Org. Chem. 2:1960;265-268
34. Katekar G.F., Moritz A.G. Aust. J. Chem. 20:1967;2235-2241
35. Bergbreit D.E., Pendergrass E. J. Org. Chem. 46:1981;219-220