Cascade synthesis with (triphenylphosphoranylidene)-ethenone as a versatile reagent for fast synthesis of heterocycles and unsaturated amides under microwave dielectric heating

Combinatorial Chemistry and High Throughput Screening

Volumn 5, Issue 7, 2002, Pages 571-574

  Westman, Jacob ^a   Orrling, K ^a  

^a Personal Chemistry AB   (Sweden)

Author keywords

(Triphenylphosphoranylidene)ethenone; Cascade reaction; Library synthesis; Microwave heating; One pot synthesis

Indexed keywords

(TRIPHENYLPHOSPHORANYLIDENE)ETHENONE; AMIDE; CARBONYL DERIVATIVE; DICHLOROETHANE; ETHYLENE DERIVATIVE; HETEROCYCLIC COMPOUND; PHOSPHORANE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; COMBINATORIAL LIBRARY; HEATING; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; CHEMISTRY; HEAT; MICROWAVE RADIATION;

AMIDES; COMBINATORIAL CHEMISTRY TECHNIQUES; HEAT; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; KETONES; MICROWAVES; ORGANOPHOSPHORUS COMPOUNDS;

EID: 0036829564     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207023330066     Document Type: Article

References (24)

1. Tietze, L.F. Chem. Rev., 1996, 96, 115.
2. Bestmann, H. J.; Schobert, R. Synthesis, 1989, 419.
3. Schobert, R.; Müller, S.; Bestmann, H. J. Synlett, 1995, 425; Schobert, R.; Löffler, J. J. Chem. Soc., Perkin Trans. 1, 1996, 2799; Schobert, R.; Siegfried, S.; Nieuwenhuyzen, M.; Millius, W.; Hampel, F. J. Chem. Soc. Perkin Trans. 1, 2000, 1723.
4. Schobert, R.; Müller, S.; Bestmann, H. J. Synlett, 1995, 425; Schobert, R.; Löffler, J. J. Chem. Soc., Perkin Trans. 1, 1996, 2799; Schobert, R.; Siegfried, S.; Nieuwenhuyzen, M.; Millius, W.; Hampel, F. J. Chem. Soc. Perkin Trans. 1, 2000, 1723.
5. Schobert, R.; Müller, S.; Bestmann, H. J. Synlett, 1995, 425; Schobert, R.; Löffler, J. J. Chem. Soc., Perkin Trans. 1, 1996, 2799; Schobert, R.; Siegfried, S.; Nieuwenhuyzen, M.; Millius, W.; Hampel, F. J. Chem. Soc. Perkin Trans. 1, 2000, 1723.
6. Schobert, R.; Siegfried, S.; Gordon, G. J. Chem. Soc., Perkin Trans 1, 2001, 2393.
7. Matthews, C. N.; Birum, G. H. Tetrahedron, 1966, 5707.
8. Bestmann, H. J.; Schobert, R. Chem. Ber., 1980, 113, 274.
9. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett., 1986, 27, 279.
10. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J.; Tetrahedron, 2001, 9225.
11. Cotterill, I. C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S. Tetrahedron Lett., 1998, 39, 1117; Öhberg, L.; Westman, J. Synlett, 2001, 1296; Stadler, A.; Kappe, C. O. J. Comb. Chem., 2001, 3, 624-630; Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett., 1999, 40, 3941.
12. Cotterill, I. C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S. Tetrahedron Lett., 1998, 39, 1117; Öhberg, L.; Westman, J. Synlett, 2001, 1296; Stadler, A.; Kappe, C. O. J. Comb. Chem., 2001, 3, 624-630; Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett., 1999, 40, 3941.
13. Cotterill, I. C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S. Tetrahedron Lett., 1998, 39, 1117; Öhberg, L.; Westman, J. Synlett, 2001, 1296; Stadler, A.; Kappe, C. O. J. Comb. Chem., 2001, 3, 624-630; Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett., 1999, 40, 3941.
14. Cotterill, I. C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S. Tetrahedron Lett., 1998, 39, 1117; Öhberg, L.; Westman, J. Synlett, 2001, 1296; Stadler, A.; Kappe, C. O. J. Comb. Chem., 2001, 3, 624-630; Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett., 1999, 40, 3941.
15. Löffler, J.; Schobert, R. Recent Res. Devel. In Org. & Bioorg. Chem., 1998, 2, 17.
16. In this project a SmithSynthesizer™ available from Personal Chemistry AB was used. This instrument is fully automated and is equipped with temperature and pressure control.
17. Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S. J.; Mingos, D. M. P. Chem. Soc. Rev., 1998, 27, 213.
18. 2, OEt), 4.57 (s, 2H, oxazolone), 5.06 (s, IH, oxazolone), 7.24-7.37 (m, 5H, ArH)., It should be noted that the yields presented in Fig. 2 are based on the product peak area as compared to total peak area of the LC chromatogram (LC purity), the triphenylphosphineoxide peak is subtracted. The yields reported should be interpreted as an indication of the yields in which the products are formed. The LC purity depends on both the structure of the substrates used and the molar ratio between them, thus the isolated yields could be higher or lower than the described LC purity value.
19. Weidner-Wells, M. A.; Fraga-Spano, S. A.; Turchi, I. J. J. Org. Chem., 1998, 63, 6319; Bhatia, B.; Jain, S.; De, A.; Bagchi, I.; Iqbal, J. Tetrahedron Lett., 1996, 371, 731; Keinan, E.; Greenspoon, N. J. Am. Chem. Soc., 1986, 108, 7314; De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett., 1997, 38, 8383.
20. Weidner-Wells, M. A.; Fraga-Spano, S. A.; Turchi, I. J. J. Org. Chem., 1998, 63, 6319; Bhatia, B.; Jain, S.; De, A.; Bagchi, I.; Iqbal, J. Tetrahedron Lett., 1996, 371, 731; Keinan, E.; Greenspoon, N. J. Am. Chem. Soc., 1986, 108, 7314; De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett., 1997, 38, 8383.
21. Weidner-Wells, M. A.; Fraga-Spano, S. A.; Turchi, I. J. J. Org. Chem., 1998, 63, 6319; Bhatia, B.; Jain, S.; De, A.; Bagchi, I.; Iqbal, J. Tetrahedron Lett., 1996, 371, 731; Keinan, E.; Greenspoon, N. J. Am. Chem. Soc., 1986, 108, 7314; De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett., 1997, 38, 8383.
22. Weidner-Wells, M. A.; Fraga-Spano, S. A.; Turchi, I. J. J. Org. Chem., 1998, 63, 6319; Bhatia, B.; Jain, S.; De, A.; Bagchi, I.; Iqbal, J. Tetrahedron Lett., 1996, 371, 731; Keinan, E.; Greenspoon, N. J. Am. Chem. Soc., 1986, 108, 7314; De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett., 1997, 38, 8383.
23. Unpublished result
24. α,β = 15.5 Hz), 8.03 (s, 1H, ArH).