Microwave-assisted Mannich-type three-component reactions

Molecular Diversity

Volumn 7, Issue 2-4, 2003, Pages 135-144

  Leadbeater, Nicholas E ^a   Torenius, Hanna M ^a   Tye, Heather ^b  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b EVOTEC UK LTD   (United Kingdom)

Author keywords

Ionic liquids; Mannich reaction; Microwave chemistry; Multi component reactions

Indexed keywords

ARTICLE; CHEMICAL REACTION; MANNICH REACTION; MICROWAVE COOKING; MICROWAVE RADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME;

CHEMISTRY, ORGANIC; COMBINATORIAL CHEMISTRY TECHNIQUES; HEATING; IONS; MICROWAVES; MODELS, CHEMICAL; POLYMERS; TEMPERATURE;

EID: 0346456942     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006822.51884.e6     Document Type: Article

References (33)

1. For reviews in the area see: (a) Larhed, M., Moberg, C. and Hallberg, A., Microwave-accelerated homogeneous catalysis in organic chemistry, Acc. Chem. Res., 35 (2002) 717-727.
2. (b) Lidström, P., Tierney, J., Wathey, B. and Westman, J., Microwave assisted organic synthesis - A review, Tetrahedron, 57 (2001) 9225-9283.
3. (c) Deshayes, S., Liagre, M., Loupy, A., Luche, J-L. and Petit, A., Microwave activation in phase transfer catalysis, Tetrahedron, 55 (1999) 10851-10870.
4. (d) Strauss, C. R., A combinatorial approach to the development of environmentally benign organic chemical preparations, Aust. J. Chem., 52(1999) 83-96.
5. For reviews on the concepts see: (a) Gabriel, C., Gabriel, S., Grant, E. H., Halstead, B. S. and Mingos, D. M. P., Dielectric parameters relevant to microwave dielectric heating, Chem. Soc. Rev., 27 (1998) 213-223.
6. (b) Baghurst, D. M. and Mingos, D. M. P., Applications of microwave dielectric heating effects to synthetic problems in chemistry, Chem. Soc. Rev., 20 (1991) 1-47.
7. (a) Loupy, A. (ed.), Microwaves in Organic Synthesis, Wiley VCH, Weinheim, 2002.
8. (b) Hayes, B. L., Microwave Synthesis, Chemistry at the Speed of Light, CEM publishing, U.S.A., 2002.
9. For examples see: (a) Westman, J., An efficient combination of microwave dielectric heating and the use of solid-supported triphenylphosphine for Wittig reactions, Org. Lett., 3 (2001) 3745-3747.
10. (b) Kuhnert, N. and Danks, T. N., Highly diastereoselective synthesis of 1,3-oxazolidines under thermodynamic control using focused microwave irradiation under solvent-free conditions, Green Chem., 3 (2001) 68-70.
11. (c) Loupy, A. and Regnier, S., Solvent-free microwave assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes, Tetrahedron Lett., 40 (1999) 6221-6224.
12. See for example: Martín-Aranda, R. M., Vicente-Rodríguez, M. A., López-Pestana, J. M., López-Peinado, A. J., Jerez, A., López-González J. de D. and Banares-Munoz, M. A., Application of basic clays in microwave activated Michael additions: Preparation of N-substituted imidazoles, J. Mol. Cat. A, 124 (1997) 115-121.
13. Ley, S. V., Leach, A. G. and Storer, R. I., A polymer-supported thionating reagent, J. Chem. Soc., Perkin Trans. 1, (2001) 358-361.
14. Leadbeater, N. E. and Torenius, H. M., A study of the ionic liquid mediated microwave heating of organic solvents, J. Org. Chem., 67 (2002) 3145-3148.
15. For reviews see: (a) Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev., 99 (1999) 2071-2083.
16. (b) Wasserscheid, P. and Keim, W. Ionic liquids - New 'solutions' for transition metal catalysis, Angew. Chem. Int. Ed., 39 (2000) 3772-3789.
17. Olivier-Bourbigou, H. and Magna, L., Ionic liquids: perspectives for organic and catalytic reactions, J. Mol. Catal. A, 182-183 (2002) 419-4-37.
18. Ren, R. X. and Wu, J. X., Mild conversion of alcohols to alkyl halides using halide-based ionic liquids at room temperature, Org. Lett., 3 (2001) 3727-3728.
19. Leadbeater, N. E. and Torenius, H. M., Ionic liquids as reagents and solvents in conjunction with microwave heating: rapid synthesis of alkyl halides from alcohols and nitriles from aryl halides, Tetrahedron, 59 (2003) 2253-2258.
20. For a review in the area see: Weber, L., The application of multi-component reactions in drug discovery, Curr. Med. Chem., 9 (2002) 2085-2093.
21. For a review on the application of microwave heating to combinatorial synthesis see: Kappe, C. O. High-speed combinatorial synthesis utilizing microwave irradiation, Curr. Opin. Chem. Biol., 6 (2002) 314-320.
22. See: (a) Kappe, C. O., Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog, Acc. Chem. Res., 33 (2000) 879-888.
23. (b) Stadler, A. and Kappe, C. O., Automated library generation using sequential microwave-assisted chemistry. Application towards the Biginelli multicomponent condensation, J. Comb. Chem., 3 (2001) 624-630.
24. Dyatkin, A. B. and Rivero, R. A., The solidphase synthesis of complex propargylamines using the combination of Sonogashira and Mannich reactions, Tetrahedron Lett., 39 (1998) 3647-3650.
25. McNally, J. J., Youngman, M. A. and Dax, S. L., Mannich reactions of a resin-bound terminal alkyne, Tetrahedron Lett., 39 (1998) 967-970.
26. Suarez, P. A. Z., Dullius, J. E. L., Einloft, S., De Souza, R. F. and Dupont, J., The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes, Polyhedron, 15 (1996) 1217-1219.
27. Yanes, E. G., Gratz, S. R., Baldwin, M. J., Robinson, S. E. and Stalcup, A. M., Capillary electrophoretic application of I-alkyl-3-methylimidazolium-based ionic liquids, Anal. Chem., 73 (2001) 3838-3844.
28. CAUTION: Organic reagents and co-solvents are heated well above their boiling point so all necessary precautions should be taken when performing such experiments. Vessels designed to withhold elevated pressures must be used. The microwave apparatus used here incorporates a protective metal cage around the microwave vessel in case of explosion. After completion of an experiment, the vessel must be allowed to cool to a temperature below the boiling point of the solvent before removal from the microwave cavity and opening to the atmosphere.
29. For a review see: Perreux, L. and Loupy, A., A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations, Tetrahedron, 57 (2001) 9199-9223.
30. CAUTION: A blast shield should be in place and vessels designed to withhold elevated pressures must be used. After completion of an experiment, the vessel must be allowed to cool before opening to the atmosphere.
31. Obrecht, D. and Villagordo, J. M. (eds), Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries, Tetrahedron Organic Chemistry Series Volume 17, 1998, Pergamon, London.
32. Ley, S. V., Baxendale, I. R., Bream, R. N., Jackson, P. S., Leach, A. G., Longbottom, D. A., Nesi, M., Scott, J. S., Storer, R. I. and Taylor, S. J., Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation, J. Chem. Soc., Perkin Trans. 1 (2000) 3815-4195.
33. 2 mixed system, Tetrahedron, 53 (1997) 12985-12902.