One-pot homolytic aromatic substitutions/HWE olefinations under microwave conditions for the formation of a small oxindole library

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3477-3480

  Teichert, Antje ^a   Jantos, Katja ^a   Harms, Klaus ^a   Studer, Armido ^a,b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; OXINDOLE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HORNER WADSWORTH EMMONS REACTION; MICROWAVE IRRADIATION; OLEFINATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 6444232904     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048759t     Document Type: Article

References (30)

1. Bräse, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
2. Bräse, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
3. For an example see: Froestl, W. Chimia 2004, 58, 54.
4. Studer, A. Angew. Chem., Int. Ed. 2000, 39, 1108.
5. For other applications of the PRE in synthesis, see: Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. Alajarín, M.; Vidal, A.; Ortín, M.-M.; Bautista, D. Synlett 2004, 991.
6. For other applications of the PRE in synthesis, see: Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. Alajarín, M.; Vidal, A.; Ortín, M.-M.; Bautista, D. Synlett 2004, 991.
7. For other applications of the PRE in synthesis, see: Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. Alajarín, M.; Vidal, A.; Ortín, M.-M.; Bautista, D. Synlett 2004, 991.
8. Fischer, H. Chem. Rev. 2001, 101, 3581. Studer, A. Chem. Eur. J. 2001, 7, 1159. Studer, A. Chem. Soc. Rev. 2004, 33, 267.
9. Fischer, H. Chem. Rev. 2001, 101, 3581. Studer, A. Chem. Eur. J. 2001, 7, 1159. Studer, A. Chem. Soc. Rev. 2004, 33, 267.
10. Fischer, H. Chem. Rev. 2001, 101, 3581. Studer, A. Chem. Eur. J. 2001, 7, 1159. Studer, A. Chem. Soc. Rev. 2004, 33, 267.
11. Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899.
12. Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
13. Leroi, C.; Bertin, D.; Dufils, P.-E.; Gigmes, D.; Marque, S.; Tordo, P.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 4943.
14. For a review on homolytic aromatic substitutions, see: Studer, A.; Bossart, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 62.
15. Prepared according to: Barluenga, J.; Bayon, A. M.; Asensio, G. Chem. Commun. 1983, 1109.
16. Axial chirality in radical chemistry: Curran, D. P.; Liu, W.; Chen, C. H.-T. J. Am. Chem. Soc. 1999, 121, 11012.
17. Cholleton, N.; Gauthier-Gillaizeau, I.; Six, Y.; Zard, S. Z. Chem. Commun. 2000, 535.
18. The microwave experiments were conducted using professional laboratory microwave equipment. A MLS-Ethos 1600 Mikrowellen System (Milestone) was used for the present studies. The reactions were run in 40 mL MLS high-pressure reaction vessels (up to 15 bar) that contain pressure control valves. An advanced temperature control system from MLS allowing direct contactless temperature monitoring was used. The microwave power is continuously and dynamically adjusted to follow the defined temperature profile. Temperature profile for the homolytic aromatic substitution: from 25 to 100°C in 10 s; from 100 to 150°C in 10 s; from 150 to 180°C in 10 s; then keep the temperature at 180°C for 2 min.
19. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968. Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. Lamberto, M.; Corbett, D. F.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1347. Ericcson, C.; Engman, L. J. Org. Chem. 2004, 69, 5143.
20. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968. Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. Lamberto, M.; Corbett, D. F.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1347. Ericcson, C.; Engman, L. J. Org. Chem. 2004, 69, 5143.
21. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968. Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. Lamberto, M.; Corbett, D. F.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1347. Ericcson, C.; Engman, L. J. Org. Chem. 2004, 69, 5143.
22. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968. Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. Lamberto, M.; Corbett, D. F.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1347. Ericcson, C.; Engman, L. J. Org. Chem. 2004, 69, 5143.
23. The same selectivity was obtained upon running the HWE reaction at 100°C. At room temperature HWE reaction did not work as controlled by TLC. The HWE reaction in THF at 100°C occurred with lower selectivity (trans:cis = 1.9:1).
24. The data for the structure of cis-8b and trans-8c have been deposited with the Cambridge Crystallographic Data Center as supplementary publications no. CCDC 241647 (cis-8b) and CCDC 241648 (trans-8c). (17) The data for the structure of 13a have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 241649.
25. In a separate experiment, the reaction was stopped after the homolytic aromatic substitution. The product was obtained in 68% yield. Compared to the N-methyl compound 6a the N-benzyl congener affords a lower yield in the homolytic aromatic substitution. We assume that the bezytic H-atoms, which are readily abstracted by TEMPO at high temperature, may be the reason for the decreased yield.
26. Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403. Marque, S.; Fischer, H.; Baier, E.; Studer, A. J. Org. Chem. 2001, 66, 1146.
27. Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403. Marque, S.; Fischer, H.; Baier, E.; Studer, A. J. Org. Chem. 2001, 66, 1146.
28. Skene, W. G.; Connolly, T. J.; Scaiano, J. C. Tetrahedron Lett. 1999, 40, 7297. Coseri, S.; Ingold, K. U. Org. Lett. 2004, 6, 1641.
29. Skene, W. G.; Connolly, T. J.; Scaiano, J. C. Tetrahedron Lett. 1999, 40, 7297. Coseri, S.; Ingold, K. U. Org. Lett. 2004, 6, 1641.
30. Ananchenko, G. S.; Fischer, H. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3604.