Access to ring-fused homo- and heteroaromatic derivatives via an initial ring-opening of 3-nitro-4-(phenylsulfonyl)thiophene

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5254-5260

  Bianchi, Lara ^a   Dell'Erba, Carlo ^a   Maccagno, Massimo ^a   Mugnoli, Angelo ^a   Novi, Marino ^a   Petrillo, Giovanni ^a   Sancassan, Fernando ^a   Tavani, Cinzia ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

THERMAL ELECTROCYCLIC REARRANGEMENTS;

ELECTRONIC PROPERTIES; RING OPENING POLYMERIZATION; SUBSTITUTION REACTIONS;

AROMATIC COMPOUNDS;

1 ARYL 4 METHYLSULFONYL 2 NITRO 3 PHENYLSULFONYL 1,3 BUTADIENE; 1,3 BUTADIENE DERIVATIVE; 3 NITRO 4 (PHENYLSULFONYL)THIOPHENE; 4 METHYLTHIO 2 NITRO 3 PHENYLSULFONYL 1 PYRROLIDINO 1,3 BUTADIENE; AROMATIC COMPOUND; HETEROCYCLIC COMPOUND; NAPHTHALENE DERIVATIVE; PHENANTHRENE DERIVATIVE; PYRROLIDINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING;

EID: 0037534011     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034264q     Document Type: Article

References (44)

1. Synthetic Exploitation of the Ring-Opening of Nitrothiophenes, Part XV. For part XIV, see ref 2a.
2. (a) Bianchi, L.; Dell'Erba, C.; Gasparrini, F.; Novi, M.; Petrillo, G.; Sancassan, F.; Tavani, C. Arkivoc 2002, 142-158. (b) Bianchi, L.; Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2002, 58, 3379-3385. (c) Armaroli, T.; Dell'Erba, C.; Gabellini, A.; Gasparrini, F.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2002, 1284-1291, and previous papers in the series. For a survey of relevant earlier literature see: (d) Spinelli, D.; Consiglio, G.; Dell'Erba, C.; Novi, M. In The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; J. Wiley: New York, 1991; Vol. 44, pp 295-396. (e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. In Topics in Heterocyclic Systems: Synthesis, Reactions and Properties; Attanasi, O. A., Spinelli, D., Eds.; Research Signpost: Trivandrum, India, 1996; Vol. 1, pp 1-12. (f) Consiglio, G.; Spinelli, D.; Dell'Erba, C.; Novi, M.; Petrillo, G. Gazz. Chim. Ital. 1997, 127, 753-769.
3. (a) Bianchi, L.; Dell'Erba, C.; Gasparrini, F.; Novi, M.; Petrillo, G.; Sancassan, F.; Tavani, C. Arkivoc 2002, 142-158. (b) Bianchi, L.; Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2002, 58, 3379-3385. (c) Armaroli, T.; Dell'Erba, C.; Gabellini, A.; Gasparrini, F.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2002, 1284-1291, and previous papers in the series. For a survey of relevant earlier literature see: (d) Spinelli, D.; Consiglio, G.; Dell'Erba, C.; Novi, M. In The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; J. Wiley: New York, 1991; Vol. 44, pp 295-396. (e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. In Topics in Heterocyclic Systems: Synthesis, Reactions and Properties; Attanasi, O. A., Spinelli, D., Eds.; Research Signpost: Trivandrum, India, 1996; Vol. 1, pp 1-12. (f) Consiglio, G.; Spinelli, D.; Dell'Erba, C.; Novi, M.; Petrillo, G. Gazz. Chim. Ital. 1997, 127, 753-769.
4. (a) Bianchi, L.; Dell'Erba, C.; Gasparrini, F.; Novi, M.; Petrillo, G.; Sancassan, F.; Tavani, C. Arkivoc 2002, 142-158. (b) Bianchi, L.; Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2002, 58, 3379-3385. (c) Armaroli, T.; Dell'Erba, C.; Gabellini, A.; Gasparrini, F.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2002, 1284-1291, and previous papers in the series. For a survey of relevant earlier literature see: (d) Spinelli, D.; Consiglio, G.; Dell'Erba, C.; Novi, M. In The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; J. Wiley: New York, 1991; Vol. 44, pp 295-396. (e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. In Topics in Heterocyclic Systems: Synthesis, Reactions and Properties; Attanasi, O. A., Spinelli, D., Eds.; Research Signpost: Trivandrum, India, 1996; Vol. 1, pp 1-12. (f) Consiglio, G.; Spinelli, D.; Dell'Erba, C.; Novi, M.; Petrillo, G. Gazz. Chim. Ital. 1997, 127, 753-769.
5. (a) Bianchi, L.; Dell'Erba, C.; Gasparrini, F.; Novi, M.; Petrillo, G.; Sancassan, F.; Tavani, C. Arkivoc 2002, 142-158. (b) Bianchi, L.; Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2002, 58, 3379-3385. (c) Armaroli, T.; Dell'Erba, C.; Gabellini, A.; Gasparrini, F.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2002, 1284-1291, and previous papers in the series. For a survey of relevant earlier literature see: (d) Spinelli, D.; Consiglio, G.; Dell'Erba, C.; Novi, M. In The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; J. Wiley: New York, 1991; Vol. 44, pp 295-396. (e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. In Topics in Heterocyclic Systems: Synthesis, Reactions and Properties; Attanasi, O. A., Spinelli, D., Eds.; Research Signpost: Trivandrum, India, 1996; Vol. 1, pp 1-12. (f) Consiglio, G.; Spinelli, D.; Dell'Erba, C.; Novi, M.; Petrillo, G. Gazz. Chim. Ital. 1997, 127, 753-769.
6. (a) Bianchi, L.; Dell'Erba, C.; Gasparrini, F.; Novi, M.; Petrillo, G.; Sancassan, F.; Tavani, C. Arkivoc 2002, 142-158. (b) Bianchi, L.; Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2002, 58, 3379-3385. (c) Armaroli, T.; Dell'Erba, C.; Gabellini, A.; Gasparrini, F.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2002, 1284-1291, and previous papers in the series. For a survey of relevant earlier literature see: (d) Spinelli, D.; Consiglio, G.; Dell'Erba, C.; Novi, M. In The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; J. Wiley: New York, 1991; Vol. 44, pp 295-396. (e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. In Topics in Heterocyclic Systems: Synthesis, Reactions and Properties; Attanasi, O. A., Spinelli, D., Eds.; Research Signpost: Trivandrum, India, 1996; Vol. 1, pp 1-12. (f) Consiglio, G.; Spinelli, D.; Dell'Erba, C.; Novi, M.; Petrillo, G. Gazz. Chim. Ital. 1997, 127, 753-769.
7. (a) Bianchi, L.; Dell'Erba, C.; Gasparrini, F.; Novi, M.; Petrillo, G.; Sancassan, F.; Tavani, C. Arkivoc 2002, 142-158. (b) Bianchi, L.; Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2002, 58, 3379-3385. (c) Armaroli, T.; Dell'Erba, C.; Gabellini, A.; Gasparrini, F.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2002, 1284-1291, and previous papers in the series. For a survey of relevant earlier literature see: (d) Spinelli, D.; Consiglio, G.; Dell'Erba, C.; Novi, M. In The Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; J. Wiley: New York, 1991; Vol. 44, pp 295-396. (e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. In Topics in Heterocyclic Systems: Synthesis, Reactions and Properties; Attanasi, O. A., Spinelli, D., Eds.; Research Signpost: Trivandrum, India, 1996; Vol. 1, pp 1-12. (f) Consiglio, G.; Spinelli, D.; Dell'Erba, C.; Novi, M.; Petrillo, G. Gazz. Chim. Ital. 1997, 127, 753-769.
8. (a) Dell'Erba, C.; Gabellini, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 2001, 57, 9025-9031.
9. (b) Dell'Erba, C.; Mugnoli, A.; Novi, M.; Pani, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2000, 903-912, and previous papers in the series.
10. Dell'Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C.; Cosimelli, B.; Spinelli, D. Tetrahedron 2001, 57, 8159-8165.
11. Dell'Erba, C.; Novi, M.; Petrillo, G.; Stagnaro, P. J. Heterocycl. Chem. 1994, 31, 861-865.
12. Armani, V.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1997, 53, 1751-1758.
13. Bianchi, L.; Fossa, P.; Maccagno, M.; Mugnoli, A.; Petrillo, G.; Tavani, C. Z. Kristallogr., in press.
14. Novi, M.; Guanti, G.; Dell'Erba, C.; Spinelli, D. J. Chem. Soc., Perkin Trans. 1 1976, 2264-2266.
15. Dell'Erba, C.; Mele, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1992, 48, 4407-4418.
16. (a) Dell'Erba, C.; Novi, M.; Petrillo, G.; Spinelli, D.; Tavani, C. Tetrahedron 1996, 52, 3313-3326.
17. (b) Dell'Erba, C.; Mugnoli, A.; Novi, M.; Pertici, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 1999, 431-435.
18. Adams, C. M.; Cerioni, G.; Hafner, A.; Kalchhauser, H.; von Philipsborn, W.; Prewo, R.; Schwenk, A. Helv. Chim. Acta 1988, 71, 1116-1142.
19. Cossu, S.; De Lucchi, O.; Fabbri, D.; Licini, G.; Pasquato, L. Org. Prep. Proc. Int. 1991, 23, 573-592. De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794.
20. Cossu, S.; De Lucchi, O.; Fabbri, D.; Licini, G.; Pasquato, L. Org. Prep. Proc. Int. 1991, 23, 573-592. De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794.
21. (a) de Koning, C. B.; Rousseau, A. L.; van Otterlo, W. A. L. Tetrahedron 2003, 59, 7-36 and references therein.
22. (b) Kajikawa, S.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 2001, 42, 3351-3354.
23. Cossu, S.; Cuomo, G.; De Lucchi, O.; Maggini, M.; Valle, G. J. Org. Chem. 1996, 61, 153-158.
24. (a) Valkovich, P. B.; Conger, J. L.; Castiello, F. A.; Brodie, T. B.; Weber, W. P. J. Am. Chem. Soc. 1975, 97, 901-902. Banciu, M. D.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Macrae, T. Aust. J. Chem. 1998, 51, 695-701. Padwa, A.; Caruso, T.; Nahm, S.; Rodriguez, A. J. Am. Chem. Soc. 1982, 104, 2865-2871.
25. (a) Valkovich, P. B.; Conger, J. L.; Castiello, F. A.; Brodie, T. B.; Weber, W. P. J. Am. Chem. Soc. 1975, 97, 901-902. Banciu, M. D.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Macrae, T. Aust. J. Chem. 1998, 51, 695-701. Padwa, A.; Caruso, T.; Nahm, S.; Rodriguez, A. J. Am. Chem. Soc. 1982, 104, 2865-2871.
26. (a) Valkovich, P. B.; Conger, J. L.; Castiello, F. A.; Brodie, T. B.; Weber, W. P. J. Am. Chem. Soc. 1975, 97, 901-902. Banciu, M. D.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Macrae, T. Aust. J. Chem. 1998, 51, 695-701. Padwa, A.; Caruso, T.; Nahm, S.; Rodriguez, A. J. Am. Chem. Soc. 1982, 104, 2865-2871.
27. (b) Olsen, R. J.; Minniear, J. C.; Mack Overton, W.; Sherrick, J. M. J. Org. Chem. 1991, 56, 989-991.
28. (a) Lewis, F. D.; Kurth, T. L.; Kalgutkar, R. S. Chem. Commun. 2001, 1372-1373. Mallory, F. B.; Mallory, C. W. In Organic Reactions; John Wiley & Sons: New York, 1984. Doyle, T. D.; Benson, W. R.; Filipescu, N. J. Am. Chem. Soc. 1976, 98, 3262-3267. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775. Rodier, J.-M.; Myers, A. B. J. Am. Chem. Soc. 1993, 115, 10791-10795. Caldwell, R. A.; Mizuno, K.; Hansen, P. E.; Vo, L. P.; Frentrup, M.; Ho, C. D. J. Am. Chem. Soc. 1981, 103, 7263-7269.
29. (a) Lewis, F. D.; Kurth, T. L.; Kalgutkar, R. S. Chem. Commun. 2001, 1372-1373. Mallory, F. B.; Mallory, C. W. In Organic Reactions; John Wiley & Sons: New York, 1984. Doyle, T. D.; Benson, W. R.; Filipescu, N. J. Am. Chem. Soc. 1976, 98, 3262-3267. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775. Rodier, J.-M.; Myers, A. B. J. Am. Chem. Soc. 1993, 115, 10791-10795. Caldwell, R. A.; Mizuno, K.; Hansen, P. E.; Vo, L. P.; Frentrup, M.; Ho, C. D. J. Am. Chem. Soc. 1981, 103, 7263-7269.
30. (a) Lewis, F. D.; Kurth, T. L.; Kalgutkar, R. S. Chem. Commun. 2001, 1372-1373. Mallory, F. B.; Mallory, C. W. In Organic Reactions; John Wiley & Sons: New York, 1984. Doyle, T. D.; Benson, W. R.; Filipescu, N. J. Am. Chem. Soc. 1976, 98, 3262-3267. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775. Rodier, J.-M.; Myers, A. B. J. Am. Chem. Soc. 1993, 115, 10791-10795. Caldwell, R. A.; Mizuno, K.; Hansen, P. E.; Vo, L. P.; Frentrup, M.; Ho, C. D. J. Am. Chem. Soc. 1981, 103, 7263-7269.
31. (a) Lewis, F. D.; Kurth, T. L.; Kalgutkar, R. S. Chem. Commun. 2001, 1372-1373. Mallory, F. B.; Mallory, C. W. In Organic Reactions; John Wiley & Sons: New York, 1984. Doyle, T. D.; Benson, W. R.; Filipescu, N. J. Am. Chem. Soc. 1976, 98, 3262-3267. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775. Rodier, J.-M.; Myers, A. B. J. Am. Chem. Soc. 1993, 115, 10791-10795. Caldwell, R. A.; Mizuno, K.; Hansen, P. E.; Vo, L. P.; Frentrup, M.; Ho, C. D. J. Am. Chem. Soc. 1981, 103, 7263-7269.
32. (a) Lewis, F. D.; Kurth, T. L.; Kalgutkar, R. S. Chem. Commun. 2001, 1372-1373. Mallory, F. B.; Mallory, C. W. In Organic Reactions; John Wiley & Sons: New York, 1984. Doyle, T. D.; Benson, W. R.; Filipescu, N. J. Am. Chem. Soc. 1976, 98, 3262-3267. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775. Rodier, J.-M.; Myers, A. B. J. Am. Chem. Soc. 1993, 115, 10791-10795. Caldwell, R. A.; Mizuno, K.; Hansen, P. E.; Vo, L. P.; Frentrup, M.; Ho, C. D. J. Am. Chem. Soc. 1981, 103, 7263-7269.
33. (a) Lewis, F. D.; Kurth, T. L.; Kalgutkar, R. S. Chem. Commun. 2001, 1372-1373. Mallory, F. B.; Mallory, C. W. In Organic Reactions; John Wiley & Sons: New York, 1984. Doyle, T. D.; Benson, W. R.; Filipescu, N. J. Am. Chem. Soc. 1976, 98, 3262-3267. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775. Rodier, J.-M.; Myers, A. B. J. Am. Chem. Soc. 1993, 115, 10791-10795. Caldwell, R. A.; Mizuno, K.; Hansen, P. E.; Vo, L. P.; Frentrup, M.; Ho, C. D. J. Am. Chem. Soc. 1981, 103, 7263-7269.
34. (b) Lewis, F. D.; Kalgutkar, R. S.; Yang, J.-S. J. Am. Chem. Soc. 2001, 123, 3878-3884. Irie, M. Chem. Rev. 2000, 100, 1685-1716. Rawal, V. H.; Jones, R. J.; Cava, M. P. Tetrahedron Lett. 1985, 26, 2423-2426.
35. (b) Lewis, F. D.; Kalgutkar, R. S.; Yang, J.-S. J. Am. Chem. Soc. 2001, 123, 3878-3884. Irie, M. Chem. Rev. 2000, 100, 1685-1716. Rawal, V. H.; Jones, R. J.; Cava, M. P. Tetrahedron Lett. 1985, 26, 2423-2426.
36. (b) Lewis, F. D.; Kalgutkar, R. S.; Yang, J.-S. J. Am. Chem. Soc. 2001, 123, 3878-3884. Irie, M. Chem. Rev. 2000, 100, 1685-1716. Rawal, V. H.; Jones, R. J.; Cava, M. P. Tetrahedron Lett. 1985, 26, 2423-2426.
37. (c) Karatsu, T.; Kitamura, A.; Zeng, H.; Arai, T.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc. Jpn. 1995, 68, 920-928.
38. Preliminary results suggest that the phenylsulfonyl goup at C(3) is, on the contrary, not essential for the cyclization process to occur.
39. (a) Novi, M.; Guanti, G.; Dell'Erba, C.; Spinelli, D. J. Chem. Soc., Perkin Trans. 1 1976, 2264-2266.
40. (b) Lawesson, S.-O. Acta Chem. Scand. 1956, 10, 1020-1023.
41. Bergbreit, D. E.; Pendergrass, E. J. Org. Chem. 1981, 46, 219-220.
42. Pearson, D. E.; Cowan, D.; Beckler, J. D. J. Org. Chem. 1959, 24, 504-509.
43. Gronowitz, S.; Pettersson, K. J. Heterocycl. Chem. 1976, 1099-1100.
44. Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Angew. Chem. 1998, 110, 1801-1804;