Synthesis of 2-alkenyl-3-alkoxycarbonylfurans by 'feist-benary- cyclocondensation' of (2,4-dioxobutylidene)phosphoranes with chloroacetaldehyde and subsequent wittig reactions

Synlett

Volumn , Issue 10, 2004, Pages 1805-1807

  Holtz, Edith ^a,b   Langer, Peter ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Chemoselectivity; Cyclizations; Furans; Wittig reaction

Indexed keywords

ACETALDEHYDE; FURAN DERIVATIVE; PHOSPHORANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HORNER REACTION; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 4143093728     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829560     Document Type: Article

References (18)

1. Römpp Lexikon Naturstoffe; Steglich, W.; Fugmann, B.; Lang-Fugmann, S., Eds.; Thieme: Stuttgart, 1997.
2. For a review of Feist-Benary and related furan syntheses, see: Friedrichsen, W. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Amsterdam, 1996, 359-363; and references cited therein.
3. For pharmacologically relevant 2-alkenyl-3-alkoxy-carbonyl-furans, see: (a) Vuligonda, V.; Garst, M. E.; Chandraratna, R. A. S. Bioorg. Med. Chem. Lett. 1999, 9, 589. (b) Rivalle, C.; Andre-Louisfert, J.; Bisangni, E. Tetrahedron 1976, 32, 829.
4. For pharmacologically relevant 2-alkenyl-3-alkoxy-carbonyl-furans, see: (a) Vuligonda, V.; Garst, M. E.; Chandraratna, R. A. S. Bioorg. Med. Chem. Lett. 1999, 9, 589. (b) Rivalle, C.; Andre-Louisfert, J.; Bisangni, E. Tetrahedron 1976, 32, 829.
5. For reactions of (2,4-dioxobutylidene)phosphoranes, see: (a) Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1995, 3719. (b) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 525. (c) Hatanaka, M.; Ishida, A.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1996, 401. (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 153. (e) Langer, P.; Holtz, E. Synlett 2003, 402; and references cited therein.
6. For reactions of (2,4-dioxobutylidene)phosphoranes, see: (a) Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1995, 3719. (b) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 525. (c) Hatanaka, M.; Ishida, A.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1996, 401. (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 153. (e) Langer, P.; Holtz, E. Synlett 2003, 402; and references cited therein.
7. For reactions of (2,4-dioxobutylidene)phosphoranes, see: (a) Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1995, 3719. (b) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 525. (c) Hatanaka, M.; Ishida, A.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1996, 401. (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 153. (e) Langer, P.; Holtz, E. Synlett 2003, 402; and references cited therein.
8. For reactions of (2,4-dioxobutylidene)phosphoranes, see: (a) Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1995, 3719. (b) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 525. (c) Hatanaka, M.; Ishida, A.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1996, 401. (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 153. (e) Langer, P.; Holtz, E. Synlett 2003, 402; and references cited therein.
9. For reactions of (2,4-dioxobutylidene)phosphoranes, see: (a) Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1995, 3719. (b) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 525. (c) Hatanaka, M.; Ishida, A.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1996, 401. (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 153. (e) Langer, P.; Holtz, E. Synlett 2003, 402; and references cited therein.
10. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
11. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
12. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
13. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
14. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
15. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
16. For synthetic applications of (furylmethylidene)phosphoranes, see: (a) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107; and references cited therein. (b) Krapivin, G. D.; Val'ter, N. I.; Zavodnik, V. E.; Kaklyugina, T. Y.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1994, 30, 296; Khim. Geterotsikl. Soedin. 1994, 3: 335. (c) Brittain, J. M.; Jones, R. A. Tetrahedron 1979, 35, 1139. (d) Schweizer, E. E.; Creasy, W. S.; Light, K. K.; Schaffer, E. T. J. Org. Chem. 1969, 34, 212. (e) Märkl, G.; Stiegler, J.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Dove, S. Helv. Chim. Acta 1997, 80, 14. (f) Tsuboi, S.; Mimura, S.; Ono, S.; Watanabe, K.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1807.
17. 3 was confirmed by HRMS (ESI, MeOH). All compounds gave satisfactory spectroscopic and analytical and/or high resolution mass data.
18. 5: C, 68.34; H, 6.37. Found: C, 68.04; H, 6.01.