Sulfur-alkyne cyclizations for formation of dihydrothiophenes and annulated thiophenes

Synthesis

Volumn , Issue 7, 2000, Pages 970-974

  McDonald, Frank E ^a   Burova, Svetlana A ^a   Huffman Jr , Larry G ^b,c  

^a EMORY UNIVERSITY   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Alkynes; Diazo compounds; Sulfur heterocycles; Thiacyclizations; Transition metals

Indexed keywords

DIHYDROTHIOPHENE DERIVATIVE; THIOPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; MOLECULAR INTERACTION; SYNTHESIS; UNITED STATES;

EID: 0033936116     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6294     Document Type: Article

References (37)

1. (a) McDonald, F. E.; Connolly, C. B.; Gleason, M. M.; Towne, T. B.; Treiber, K. D. J. Org. Chem. 1993, 58, 6952.
2. (b) McDonald, F. E.; Zhu, H. Y. H. J. Am. Chem. Soc. 1998, 120, 4246.
3. (c) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103.
4. McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687.
5. McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691.
6. Press, J. B. in Chemistry of Heterocyclic Compounds:Thiophene and Its Derivatives, Gronowitz, S., Ed.; Wiley: New York, Vol. 44, Part 1, pp 353-456, 1985; Vol. 44, Part 4, pp 397-502, 1991.
7. Press, J. B. in Chemistry of Heterocyclic Compounds:Thiophene and Its Derivatives, Gronowitz, S., Ed.; Wiley: New York, Vol. 44, Part 1, pp 353-456, 1985; Vol. 44, Part 4, pp 397-502, 1991.
8. McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363.
9. Chan, T. H.; Finkenbine, J. R. J. Am. Chem. Soc. 1972, 94, 2880.
10. 3N and/or THF).
11. 3N and THF (without metal catalyst) gave no reaction at room temperature, indicating that the metal carbonyl is required for this transformation.
12. 2O. Both homopropargylic alcohols were prepared by standard methods, as described by: Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; p 67, and p 95.
13. We have not unambiguously determined whether this complex is π-bound to the alkene or σ-bound to the sulfur atom. In no case have we observed Fischer-type thiacarbene products.
14. Similar transformations of alkynylthiols have been reported under halonium (Ref. 11a), radical (Ref. 11b) and basic (Refs 11c-e) reaction conditions. (a) Ren, X.-F.; Turos, E.; Lake, C. H.; Churchill, M. R. J. Org. Chem. 1995, 60, 6468.
15. (b) DuPuy, C.; Crozet, M.-P.; Surzur, J.-M. Bull. Soc. Chim. Fr. 1980, II-361.
16. (c) DuPuy, C.; Surzur, J.-M. Bull. Soc. Chim. Fr. 1980, II-353.
17. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607.
18. (e) Hanekamp, J. C.; Klusener, P. A. A.; Brandsma, L. Synth. Commun. 1989, 19, 2691.
19. Brandsma, L.; Hommes, H.; Verkruijsse, H. D.; deJong, R. L. P. Red. Trav. Chim. Pays-Bas 1985, 104, 226.
20. (a) Schroth, W.; Jordan, H.; Spitzner, R. Tetrahedron Lett. 1995, 36, 1421.
21. (b) Maercker, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 972.
22. (a) Jones, C. D.; Jevnikar, M. G.; Pike, A. J.; Peters, M. K.; Black, L. J.; Thompson, A. R.; Falcone, J. F.; Clemens, J. A. J. Med.Chem. 1984, 27, 1057. Compound 17 is also a key intermediate for the synthesis of other biologically active compounds:
23. (b) Palkowitz, A. D.; Glasebrook, A. L.; Thrasher, K. J.; Hauser, K. L.; Short, L. L.; Phillips, D. L.; Muehl, B. S.; Sato, M.; Shetler, P. K.; Cullinan, G. J.; Pell, T. R.; Bryant, H. U. J. Med. Chem. 1997, 40, 1407.
24. (c) Leichtl, S.; von Angerer, E. Arch. Pharm. Pharm. Med. Chem. 1998, 331, 283.
25. (d) Schmid, C. R.; Sluka, J. P.; Duke, K. M. Tetrahedron Lett. 1999, 40, 675.
26. (e) Takeuchi, K.; Kohn, T. J.; Sall, D. J.; Denney, M. L.; McCowan, J. R.; Smith, G. F.; Gifford-Morre, D. S. Bioorg. Med. Chem. Lett. 1999, 9, 759.
27. (f) Pinney, K. G.; Bounds, A. D.; Dingeman, K. M.; Mocharla, V. P.; Pettit, G. R.; Bai, R.; Hamel, E. Bioorg. Med. Chem. Lett. 1999, 9, 1081.
28. Sato, M.; Grese, T. A.; Dodge, J. A.; Bryant, H. U.; Turner, C. R. J. Med. Chem. 1999, 42, 1.
29. Bradley, D. A.; Godfrey, A. G.; Schmid, C. R. Tetrahedron Lett. 1999, 40, 5155.
30. Prepared using the general procedure of: Mital, R. L.; Suresh, K. J. J. Chem. Soc. (C) 1969, 2148.
31. Ranken, P. F.; McKinnie, B. G. J. Org. Chem. 1989, 54, 2985. The published representative procedure does not mention the use of solvent, but we found that thiomethylated compound 20 was obtained from p-anisidine (19) only when o-xylene or mesitylene were used as solvents.
32. 3; 85% yield). For a general procedure, see: Kotlyrevskii, J. L.; Bardamova, M. I. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1964, 11, 1969.
33. (a) Albertazzi, A.; Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Org. Chem. 1984, 49, 4482.
34. (b) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1985, 1390.
35. (a) Minisci, F.; Coppa, F.; Fontana, F.; Pianese, G.; Zhao, L. J. Org. Chem. 1992, 57, 3829.
36. (b) Citterio, A.; Minisci, F.; Albinati, A.; Bruckner, S. Tetrahedron Lett. 1980, 21, 2909.
37. The use of NaI/acetone affords lower yields (25-30%) of annulated products 24 and 17 accompanied by significant amounts of 4-iodo-3-thiomethylanisole and the reduction product 3-thiomethylanisole.