Intramolecular thia-anti-Michael addition of a sulfur anion to enones: A regiospecific approach to multisubstituted thiophene derivatives

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8006-8010

  Li, Yan ^a   Liang, Fushun ^a   Bi, Xihe ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

MULTISUBSTITUTED THIOPHENE; TANDEM FRAGMENTATION; TETRASUBSTITUTED THIOPHENE;

AMINES; KETONES; NEGATIVE IONS; POLYOLEFINS; SUBSTITUTION REACTIONS;

SULFUR;

1,3 DITHIOLANE DERIVATIVE; 4 HYDROXYTHIOPHENE 3 CARBOXAMIDE; ACETAL DERIVATIVE; AMINE; ANION; DITHIOL DERIVATIVE; KETENE DERIVATIVE; SULFUR; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; INTRAMOLECULAR THIA ANTI MICHAEL ADDITION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 33750027188     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0611420     Document Type: Article

References (73)

1. (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
2. (b) Jung, M. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 1-67.
3. (c) Bergman, E. D.; Ginsburg, D.; Pappo, R. Org. React. 1959, 10, 179-555.
4. (d) Krause, N.; Hoffmann-Roder, A. Synthesis 2001, 171-196.
5. Reactions with β,β-bis(trifluoromethyl) carbonyl compounds as conjugate acceptors: (a) Coyanis, E. M.; Della Védova, C. O.; Haas, A.; Winter, M. J. Fluorine Chem. 2002, 117, 185-192.
6. (b) Keese, R.; Hinderling, C. Synthesis 1996, 695-696.
7. (c) Hass, A.; Lieb, M.; Schelvis, M. J. Fluorine Chem. 1997, 83, 133-143.
8. (d) Martin, V.; Molines, H.; Wakselman, C. J. Org. Chem. 1992, 57, 5530-5532.
9. (e) Eberle, M. K.; Keese, R. Helv. Chim. Acta 1998, 81, 182-186.
10. Reactions with benzoyl(trifluoromethyl)acetylene as a conjugate acceptor: Bumgardner, C. L.; Bunch, J. E.; Whangbo, M. H. J. Org. Chem. 1986, 51, 4082-4083.
11. Additions of organocopper reagents and heteroatom nucleophiles to 1-phenylseleno-2-(p-toluenesulfonyl)ethyne: (a) Back, T. G.; Bethell, R. J.; Parvez, M.; Wehrli, D. J. Org. Chem. 1998, 63, 7908-7919.
12. (b) Back, T. G.; Wehrli, D. Tetrahedron Lett. 1995, 36, 4737-4740.
13. Additions of organolithium reagents to α,β-unsaturated secondary amides: Klumpp, G. W.; Mierop, A. J. C.; Vrielink, J. J.; Brugman, A.; Schakel, M. J. Am. Chem. Soc. 1985, 107, 6740-6742.
14. Intramolecular nucleophilic addition reactions to carbon-carbon triple bonds: (a) Rudorf, W.-D.; Schwarz, R. Synlett 1993, 369-374.
15. (b) Rudorf, W.-D.; Schwarz, R. Tetrahedron Lett. 1987, 28, 4267-4270.
16. Addition of organolithium reagents to secondary chiral cinnamyl amides: (a) Bremand, N.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1999, 40, 3379-3382.
17. (b) Bremand, N.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1999, 40, 3383-3386.
18. Addition of organolithium reagents to α,β-unsaturated carboxylic acids: (a) Plunian, B.; Vaultier, M.; Mortier, J. Chem. Commun. 1998, 81-82,
19. (b) Aurell, M. J.; Banuls, M. J.; Mestres, R.; Munoz, E. Tetrahedron 1999, 55, 831-846.
20. (c) Aurell, M. J.; Banuls, M. J.; Mestres, R.; Munoz, E. Tetrahedron 1999, 57, 1067-1074.
21. (a) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596.
22. (b) Shvo, Y.; Arisha, A. H. I. J. Org. Chem. 2001, 66, 4921-4922.
23. (c) Shim, J. O.; Park, J. C.; Cho, C. S.; Shim, S. C.; Yamamoto, Y. Chem. Commun. 2002, 852-853.
24. (a) Kamimura, A.; Murakami, N.; Yokota, K.; Shirai, M.; Okamoto, H. Tetrahedron Lett. 2002, 43, 7521-7523.
25. (b) Kamimura, A.; Murakami, N.; Kawahara, F.; Yokota, K.; Omata, Y.; Matsuura, K.; Oishi, Y.; Morita, R.; Mitsudera, H.; Suzukawa, H.; Kakehi, A.; Shirai, M.; Okamoto, H. Tetrahedron 2003, 59, 9537-9546.
26. Remarkable reports on redirecting the regioselectivity of addition of a nucleophile from the classical β-addition mode to an α-addition, see: ref 9a and Trost, B. M.; Gunzner, J. L.; Yasukata, T. Tetrahedron Lett. 2001, 42, 3775-3778.
27. For reviews on the synthesis and application of α-oxo ketene-(S,S)acetals, see: (a) Dieter, R. K. Tetrahedron 1986, 42, 3029-3096.
28. (b) Tominaga, Y. J. Heterocycl. Chem. 1989, 26, 1167-1204.
29. (c) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423-5506.
30. (d) Kolb, M. Synthesis 1990, 171-190.
31. (e) Junjappa, H.; Ila, H. Phosphorus, Sulfur Silicon 1994, 35, 95-96.
32. (f) Junjappa, H.; Ila, H.; Mohanta, P. K. In Progress in Heterocyclic Chemistry; Gribble, G. H., Gilchrist, L. T., Eds.; Pergamon Press: Oxford, 2001; Vol. 13, Chapter 1, pp 1-24.
33. Selective examples: (a) Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. J. Org. Chem. 2003, 68, 9148-9150.
34. (b) Sun, S.; Liu, Y.; Liu, Q.; Zhao, Y.; Dong, D. Synlett 2004, 1731-1734.
35. (c) Zhao, Y.-L.; Liu, Q.; Zhang, J.-P.; Liu, Z.-Q. J. Org. Chem. 2005, 70, 6913-6917.
36. (d) Yin, Y.; Wang, M.; Liu, Q.; Hu, J.; Sun, S.; Kang, J. Tetrahedron Lett. 2005, 46, 4399-4402.
37. (e) Ouyang, Y.; Dong, D.; Yu, H.; Liang, Y.; Liu, Q. Adv. Synth. Catal. 2006, 348, 206-210.
38. annulation: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578-4579.
39. (b) Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580-3582.
40. (c) Zhao, L.; Liang, F.; Bi, X.; Sun, S.; Liu, Q. J. Org. Chem. 2006, 71, 1094-1098.
41. (d) Bi, X.; Dong, D.; Li, Y.; Liu, Q. J. Org. Chem. 2005, 70, 10886-10889.
42. Samuel, R.; Nair, S. K.; Asokan, C. V. Synlett 2001, 1804-1806.
43. (a) Bi, X.; Liu, Q.; Sun, S.; Liu, J.; Pan, W.; Zhao, L.; Dong, D. Synlett 2005, 49-54.
44. (b) Bi, X.; Zhang, J.; Liu, Q.; Tan, J.; Li, B. Unpublished results.
45. Sugi, R.; Yokoyama, A.; Furuyama, T.; Uchiyama, M.; Yokozawa, T. J. Am. Chem. Soc. 2005, 127, 10172-10173.
46. For the ring opening of 1,3-dithiolane, please see: (a) Luh, T.-Y.; Lee, C.-F. Eur. J. Org. Chem. 2005, 3875-3885.
47. (b) Tanimoto, S.; Oida, T.; Hatanaka, K.; Sugimoto, T. Tetrahedron Lett. 1981, 22, 655-658.
48. (c) Tanimoto, S.; Oida, T.; Kokubo, T.; Okano, M. Bull. Chem. Soc. Jpn. 1982, 55, 339-340.
49. (d) Wilson, S. R.; Georgiadis, G. M.; Khatri, H. N.; Bartmess, J. E. J. Am. Chem. Soc. 1980, 102, 3577-3583.
50. (e) Wilson, S. R.; Caldera, P.; Jester, M. A. J. Org. Chem. 1982, 47, 3319-3321.
51. (f) Ikehira, H.; Tanimoto, S.; Oida, T.; Okano, M. J. Org. Chem. 1983, 48, 1120-1122.
52. (g) Ikehira, H.; Tanimoto, S.; Oida, T. Bull. Chem. Soc. Jpn. 1983, 56, 2537-2538.
53. The thiophene ring structure is widespread in nature, and many of the thiophene derivatives are biologically active. Thiophene derivatives are also widely utilized as functional materials in dyes and liquid crystals and as components of organic conducting polymers. For reviews, see: (a) Russell, R. K.; Press, J. B. In Comprehensive Heterocyclic Chemistry II, Katritzky, A. R., Rees, C. W., Scriven, E. W. F., Padwa, A., Eds.; Pergamon: New York, 1996; Vol. 2, pp 679-729.
54. (b) Goeb, S.; De Nicola, A.; Ziessel, R. Synlett 2005, 1169-1177.
55. (c) Jesberger, M.; Davis, T. P.; Barner, L. Synthesis 2003, 1929-1958.
56. Selected examples for the fascinating electronic and optical properties: (a) Roncali, J. Chem. Rev. 1992, 92, 711-738.
57. (b) Nalwa, H. S. Adv. Mater. 1993, 5, 341-346.
58. (c) Su, Y. Z.; Lin, J. T.; Tau, Y.-T.; Ko, C.-W.; Lin, S.-C; Sun, S.-S. Chem. Mater. 2002, 14, 1884-1890.
59. (d) Shirota, Y.; Kinoshita, M.; Noda, T.; Okumoto, K.; Ohara, T. J. Am. Chem. Soc. 2000, 122, 11021-11022.
60. (e) Zen, A.; Bilge, A.; Galbrecht, F.; Alle, R.; Meerholz, K.; Grenzer, J.; Neher, D.; Scherf, U.; Farrell. T. J. Am. Chem. Soc. 2006, 128, 3914-3915.
61. For representative reports on the synthesis of substituted thiophenes from open-chain precursors, see: (a) Bartolo, G.; Giuseppe, S.; Alessia, F. Org. Lett. 2000, 2, 351-352.
62. (b) Fazio, A.; Gabriele, B.; Salerno, G.; Destri, S.; Tetrahedron 1999, 55, 485-503.
63. (c) Ong, C. W.; Chen, C. M.; Wang, L. F.; Shieh, P. C. Tetrahedron Lett. 1998, 39, 9191-9192.
64. (d) Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096-6097.
65. (e) Marshall, J. A.; DuBay, W. J. Synlett 1993, 209-210.
66. (f) Wang, M.; Ai, L.; Zhang, J.-Y.; Liu, Q.; Gao, L.-X. Chin. J. Chem. 2002, 20, 1591-1597.
67. 3N the normal Michael adduct was obtained; however, the corresponding anti-Michael adduct was formed when 3-(4-pyridyl)acrylic acid was taken as the Michael acceptor under the identical conditions.
68. (b) Lewandowska, E.; Chatfield, D. C. Eur. J. Org. Chem. 2005, 3297-3303.
69. (c) Chatfield, D. C.; Augsten, A.; D'Cunha, C.; Lewandowska, E.; Wnuk, S. F. Eur. J. Org. Chem. 2004, 313-322.
70. X-ray diffraction data for 2a and 2i have been deposited in the Cambridge Crystallographic Data Centre with supplementary publication numbers of CCDC 299096 (2a) and 603091 (2i). The CIF files are also available in the Supporting Information.
71. (a) Rudorf, W.-D.; Schwarz, R. Synlett 1993, 369-374.
72. (b) Rudorf, W.-D.; Schwarz, R. Tetrahedron Lett. 1987, 37, 4267-4270. In these two reports, reaction of 4-phenyl-3-butyn-2-one and 1-phenyl-1-pentyn-3- one with carbon disulfide in the presence of sodium hydride in DMF followed by alkylation afforded a mixture of isomeric 2-alkylthio-6-phenyl-4H-thiopyrans and 5-alkylthio-2-benzylidene-3(2H)-thiophenones in a ratio of about 4:1.
73. 1H NMR spectrum of 2a-D indicates that the methylene group is deuterated during the intramolecular thia-anti-Michael addition process.