Integrating Microwave-Assisted Synthesis and Solid-Supported Reagents

Microwave Assisted Organic Synthesis

Volumn , Issue , 2009, Pages 133-176

  Baxendale, Ian R ^a   Lee, Ai Lan ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Acylation of functional groups fundamental chemical manipulations in organic chemistry; Doping effects of solvent combinations; Fisher esterification reaction using continuous batch flow reactor; Integrating microwave assisted synthesis and solid supported reagents; Microwave flash heating and set of reaction parameters; Microwave heating of reactions; Microwave assisted chemical processing; Migration of reacting species; Novel monomer building blocks

Indexed keywords

EID: 84891307769     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781444305548.ch6     Document Type: Chapter

References (182)

1. Gedye, R., Smith, F., Westaway, K., Ali, H., Baldisera, L. Laberge, and L., Rousell, J., The use of microwave ovens for rapid organic synthesis, Tetrahedron Lett., 1986, 27, 279.
2. Giguere, R.J., Bray, T.L., Duncan, S.M. and Majetich, G., Application of commercial microwave ovens to organic synthesis, Tetrahedron Lett., 1986, 27, 4945.
3. Maoz, R., Cohen, H. and Sagiv, J., Specific nonthermal chemical structural transformation induced by microwaves in a single amphiphilic bilayer self-assembled on silicon, Langmuir, 1998, 14, 5988.
4. Stuerga, D.A.C. and Gaillard, P., Microwave athermal effects in chemistry: a myth's autopsy 2. Orienting effects and thermodynamic consequences of electric field, J. Microw. Power Electromagn. Energy, 1996, 31, 101.
5. Saillard, R., Poux, M., Berlan, J. and Audhuypeaudecerf, M., Microwave-heating of organic-solvents-thermal effects and field modeling, Tetrahedron, 1995, 51, 4033.
6. Pagnotta, M., Pooley, C.L.F., Gurland, B. and Choi, M., Microwave activation of the mutarotation of alpha-d-glucose-an example of an intrinsic microwave effect, J. Phys. Org. Chem., 1993, 6, 407.
7. Stuerga, D., Gonon, K. and Lallemant, M., Microwave heating as a new way to induce selectivity between competitive reactions-application to isomeric ratio control in sulfonation of naphthalene, Tetrahedron, 1993, 49, 6229.
8. Molina, A., Vaquero, J.J., Garcianavio, J.L. and Alvarezbuilla, J., One-pot Graebe-Ullmann synthesis of gamma-carbolines under microwave irradiation, Tetrahedron Lett., 1993, 34, 2673.
9. Raner, K.D., Strauss, C.R., Vyskoc, F. and Mokbel, L., A comparison of reaction-kinetics observed under microwave irradiation and conventional heating, J. Org. Chem., 1993, 58, 950.
10. Raner, K.D. and Strauss, C.R., Influence of microwaves on the rate of esterification of 2, 4, 6-trimethylbenzoic acid with 2-propanol, J. Org. Chem., 1992, 57, 6231.
11. Adamek, F. and Hajek, M., Microwave-assisted catalytic addition of halocompounds to alkenes, Tetrahedron Lett., 1992, 33, 2039.
12. Abramovitch, R.A., Abramovitch, D.A., Iyanar, K. and Tamareselvy, K., Application of microwave-energy to organic-synthesis-improved technology, Tetrahedron Lett., 1991, 32, 5251.
13. Wei, J.H. and DeLong, J.D., Comparison of microwave and thermal cure of epoxy-resins, Polym. Eng. Sci., 1993, 33, 1132.
14. Wei, J., DeMuse, M. and Hawley, M.C., Kinetics modelling and time-temperature-transformation diagram of microwave and thermal cure of epoxy-resins, Polym. Eng. Sci., 1995, 35, 461.
15. Fang, X., Hutcheon, R. and Scola, D.A., Microwave syntheses of poly(epsilon-caprolactam-co-epsilon-caprolactone), J. Polym. Sci., PartA: Polym. Chem., 2000, 38, 1379.
16. Westaway, K. and Gedye, R.N., The question of specific activation of organic reactions by microwaves, J. Microw. Power Electromagn. Energy., 1995, 30, 219.
17. Haswell, S.J. and Howarth, N., Perturbation of a solid phase separation process by anon-thermal microwave effect, Anal. Chim. Acta, 1999, 387, 113.
18. Caddick, S., Microwave-assisted organic-reactions, Tetrahedron, 1995, 51, 10403.
19. Strauss, C.R. and Trainer, R.W., Invited review-developments in microwave-assisted organic-chemistry, Aust. J. Chem., 1995, 48, 1665.
20. Galema, S.A., Microwave chemistry, Chem. Soc. Rev., 1997, 26, 233.
21. Ranu, B.C., Guchhait, S.K., Gosh, K. and Patre, A., Construction of bicyclo[2.2.2]octanone systems by microwave-assisted solid phase Michael addition followed by Al2O3-mediated intramolecular aldolisation. An eco-friendly approach, Green Chem., 2000, 2, 5.
22. Loupy, A. and Perreux, L., A tentative rationalization ofmicrowave effects in organic synthesis according to the reaction medium, and mechanistic considerations, Tetrahedron, 2001, 57, 9199.
23. Lidstrom, P., Tierney, J., Wathey, B. and Westman, J., Microwave assisted organic synthesis-a review, Tetrahedron, 2001, 57, 9225.
24. Loupy, A., Microwaves in Organic Synthesis, Wiley-VCH, Berlin, 2002.
25. Baxendale, I.R., Lee, A.-L. and Ley, S.V., A concise synthesis of carpanone using solid-supported reagents and scavengers, J. Chem. Soc., Perkin Trans. 1, 2002, 1850.
26. Baxendale, I.R. and Ley, S.V., Polymer-supported reagents for multi-step organic synthesis: application to the synthesis of sildenafil, Bioorg. Med. Chem. Lett., 2000, 10, 1983.
27. Baxendale, I.R., Storer, R.I. and Ley, S.V., Supported reagents and scavengers in multi-step organic synthesis, In: Buchmeiser, M. (Ed.) Supported Reagents and Scavengers in Multi-Step Organic Synthesis, Wiley-VCH, Berlin, 2003.
28. Durand-Reville, T., Gobbi, L.B., Gray, B.L., Ley, S.V. and Scott, J.S., Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence, Org. Lett., 2002, 4, 3847.
29. Habermann, J., Ley, S.V. and Scott, J.S., Synthesis of the potent analgesic compound (±)-epibatidine using an ochestrated multi-step sequence of polymer-supported reagents, J. Chem. Soc., Perkin Trans. 1, 1999, 1253.
30. Kiyota, H., Dixon, D.J., Luscombe, C.K., Hettstedt, S. and Ley, S.V., Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a Tunicate Didemnum sp., Org. Lett., 2002, 4, 3223.
31. Ley, S.V. and Mynett, D.M., Microwave promoted hydrolysis of esters absorbed on alumina: a new depro-tection method for pivaloyl groups, Synlett, 1993, 793.
32. Siu, J., Baxendale, I.R. and Ley, S.V., Microwave assisted Leimgruber-Batcho reaction for the preparation of indoles, azaindoles and pyrroylquinolines, Bioorg. Med. Chem., 2004, 2, (2) 160.
33. Ley, S.V., Baxendale, I.R., Bream, R.N., Jackson, P.S., Leach, A.G. et al., 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.
34. Ley, S.V., Baxendale, I.R., Brusotti, G., Caldarelli, M., Massi, A. et al., Solid-supported reagents for multi-step organic synthesis: preparation and application, Farmaco, 2002, 57, 321.
35. Ley, S.V. and Baxendale, I.R., Organic synthesis in a changing world, Chem. Rev., 2002, 2, 377.
36. Ley, S.V., Baxendale, I.R. and Sherrington, D.S. (Ed.), Supported Catalysts Applications, Royal Society of Chemistry, Cambridge, 2000.
37. Bose, A.K., Manhas, M.S., Banik, B.K. and Robb, E.W., Microwave-induced organic-reaction enhancement (MORE) chemistry-techniques for rapid, safe and inexpensive synthesis, Res. Chem. Intermed., 1994, 20, 1.
38. Banik, B.K., Manhas, M.S., Kaluza, Z., Barakat, K.J. and Bose, A.K., Microwave-induced organic-reaction enhancement chemistry 4. Convenient synthesis of enantiopure α-hydroxy-ß-lactams, Tetrahedron Lett., 1992, 33, 3603.
39. Bose, A.K., Manhas, M.S., Ghosh, M., Shah, M., Raju, V.S. et al., Microwave-induced organic-reaction enhancement chemistry 2. Simplified techniques, J. Org. Chem., 1991, 56, 6968.
40. Banik, B.K., Manhas, M.S., Newaz, S.N. and Bose, A.K., Facile preparation of carbapenem synthons via microwave-induced rapid reaction, Bioorg. Med. Chem. Lett., 1993, 3, 2363.
41. Manhas, M.S., Banik, B.K., Mathur, A., Vincent, J.E. and Bose, A.K., Vinyl-ß-lactams as efficient synthons. Eco-friendly approaches via microwave assisted reactions, Tetrahedron, 2000, 56, 5587.
42. Bose, A.K., Banik, B.K., Mathur, C., Wagle, D.R. and Manhas, M.S., Polyhydroxy amino acid derivatives via beta-lactams using enantiospecific approaches and microwave techniques, Tetrahedron, 2000, 56, 5603.
43. Baghurst, D.R. and Mingos, D.M.P., Superheating effects associated with microwave dielectric heating, J. Chem. Soc., Chem. Commun., 1992, 674.
44. Baghurst, D.R. and Mingos, D.M.P., A new reaction vessel for accelerated syntheses using microwave dielectric super-heating effects, J. Chem. Soc., Dalton Trans., 1992, 1151-1155.
45. Marand, E., Baker, K.R. and Graybeal, J.D., Comparison of reaction-mechanisms of epoxy-resins undergoing thermal and microwave cure from in situ measurements of microwave dielectric-properties and infrared-spectroscopy, Macromolecules, 1992, 25, 2243.
46. Baker, K.R., Marand, E. and Graybeal, J.D., Abstr. Pap. Am. Chem. Soc., 1992, 66, 422.
47. Wei, J.H., DeLong, J.D. and Hawley, M.C., Comparison of microwave and thermal cure of epoxy-resins, Polym. Eng. Sci., 1993, 33, 1132.
48. Wei, J., DeLong, J.D. and Hawley, M.C., Kinetics modelling and time-temperature-transformation diagram of microwave and thermal cure of epoxy-resins, Polym. Eng. Sci., 1995, 35, 461.
49. Lewis, D.A., Summers, J.D., Ward, T.C. and McGrath, J.E., Polym. Prepr., 1987, 28, 330.
50. Lewis, D.A., Summers, J.D., Ward, T.C. and McGrath, J.E., Accelerated imidization reactions using microwave-radiation, J. Polym. Sci., Pol. Chem., 1992, 30, 1647.
51. Matsumoto, M. and Miyata, Y. EMC '98 ROMA, 1998, pp 523.
52. Kato, Y., Sugimoto, S., Shinohara, K., Tezuka, N., Kagotani, T. et al., Magnetic properties and microwave absorption properties of polymer-protected cobalt nanoparticles, Mater. Trans., JIM, 2002, 43, 406.
53. 7 compound, Mater. Trans., JIM, 2000, 41, 1172.
54. Yoshida, S., Sato, M., Sugawara, E. and Shimada, Y., Permeability and electromagnetic-interference characteristics of Fe-Si-Al alloy flakes polymer composite, J. Appl. Phys., 1999, 85, 4636.
55. Roussy, G., Jassm, S. and Thiebaut, J.M., Modeling of a fluidized-bed irradiated by a single or a multi-mode electric microwave field distribution, J. Microw. Power Electromagn. Energy, 1995, 30, 178.
56. Thomas, J.R. and Faucher, F., Thermal modeling of microwave heated packed and fluidized bed catalytic reactors, J. Microw. Power Electromagn. Energy, 2000, 35, 165.
57. Metaxas, A.C. and Meredith, R.J., Industrial Microwave Heating, Peter Peregrinus Ltd., London, 1983.
58. For an excellent review on the area the authors recommend Lanz, J.E., A Numerical Model of Thermal Effects in a Microwave Irradiated Catalyst Bed (PhD thesis), Virginia Polytechnic Institute and State University, Blacksburg, Virginia, 1998.
59. Barringer S.A., Ayappa, G., Davis, E.A., Davis, H.T. and Gordon, J., Int. J. Food Sci., 1995, 60, 5, 1132.
60. Sasaki, K., Shimada, A., Hatae, K. and Shimada, A., Agric. Biol. Chem., 1988, 52, 2273.
61. Stratton, J.A., Electromagnetic Theory, McGraw-Hill, New York, 1941, p. 1.
62. Thomas, C., Perl, J.P. and Wasan, D.T.J., Colloid Interface Sci., 1990, 139, 1.
63. Ayappa, K.G. and SenGupta, T.J., Microwave heating in multiphase systems: evaluation of series solutions, Eng. Math., 2002, 44, 155.
64. Daniels, V., Dielectric Relaxation, Academic Press, London, 1967.
65. Fröhlich, H., Theory of Dielectrics, Oxford University Press, London, 1958.
66. Debye, P., Polar Molecules, Chemical Catalog, New York, 1929.
67. Whittaker, A.G. and Mingos, D.M.P., The application of microwave-heating to chemical synthesis, J. Microwave Power Electromagn. Energy, 1994, 29, 195.
68. Maxwell, J.C., A Treatise on Electricity and Magnetism, Vol. 1, 3rd. ed., Clarendon Press, Oxford, 1891, Ch. IX.
69. Wagner, K.W., Erklarung der dielektrischen Nachwirkungs vorgange auf Grund Maxwellscher Vorstellungen, Arch. Elektrotech., 1914, 2, S371.
70. Sillars, R.W.J., Dielectric properties, Proc. Inst. Elect. Eng., 1937, 100, 199.
71. Gibson, C., Matthews, I. and Samuel, A., Microwave enhanced diffusion in polymeric materials, J. Microwave Power Electromagn. Energy, 1998, 23, 17.
72. Hedrick, J.C., Lewis, D.A., Lyle, G.D., Wu, S.D., Ward, T.C. et al., Microwave processing of functionalized poly(arylene ether ketones), Abstr. Pap. Am. Chem. Soc., 1989, 197, 92-PMSE.
73. Haggag, K., Tinctoria 1991, 88, 66.
74. Kim, S.S., Leem, S.G., Ghim, H.D., Kim, J.H., and Lyoo, W.S., Microwave heat dyeing of polyester fabric, Fibers Polymers, 2003, 4, 204.
75. Jeon, J.Y. and Kim, H.Y., Microwave irradiation effect on diffusion of organic molecules in polymers, Eur. Polym. J., 2000, 36, 895.
76. Lai, C.P., Tsai, M.H., Chen, M., Chang, H.S., and Tay, H.H., Morphology and properties of denture acrylic resins cured by microwave energy and conventional water bath, Dental Mater., 2004, 20, 133.
77. Zong, L.M., Zhou, S.J., Sun, R.S., Kempel, L.C. and Hawley, M.C., Dielectric analysis of a crosslinking epoxy resin at a high microwave frequency, J. Polym. Sci. Part B: Polym. Phys., 2004, 42, 2871.
78. Jacob, J., Chia, L.H.L. and Boey, F.Y.C., Thermal and nonthermal interaction of microwave-radiation with materials, J. Mater. Sci., 1995, 30, 5321.
79. Jacob, J., Chia, L.H.L. and Boey, F.Y.C., Comparative study of methyl-methacrylate cure by microwave-radiation versus thermal-energy, Polym. Test, 1995, 14, 343.
80. Sengwa, R.J., Chaudhary, R. and Kaur, K., Microwave dielectric relaxation study of poly(propylene glycol) in dilute solution, Polym. Int., 2000, 49, 1308.
81. Sengwa, R.J. and Kaur, K., Microwave absorption in oligomers of ethylene glycol, Indian J. Biochem. Biophys., 1999, 36, 325.
82. Semenov, A.N., Dynamics of irregular copolymers, Phys. Rev. E, 1999, 60, 3076.
83. Leon, C., Ngai, K.L. and Roland, C.M., Relationship between the primary and secondary dielectric relaxation processes in propylene glycol and its oligomers, J. Chem. Phys., 1999, 110, 11585.
84. Kakizaki, M. and Hideshima, T., Effect of distribution of free volume on concentration dependence of dielectric relaxation in water mixtures with poly(ethylene glycol) and glucose, Jpn. J. Appl. Phys., Part 1, 1998, 37, 900.
85. Sengwa, R.J., Solvent effects on microwave dielectric relaxation in poly(ethylene glycols), Polym. Int., 1998, 45, 43.
86. Bergman, R., Borjesson, L., Torell, L.M. and Fontana, A., Dynamics around the liquid-glass transition in poly(propylene-glycol) investigated by wide-frequency-range light-scattering techniques, Phys. Rev. B, 1997, 56, 11619.
87. Kakizaki, M., Anada, U. and Hideshima, T., Distribution of free-volume and dielectric alpha-relaxation in glass-forming liquid-mixtures, Jpn. J. Appl. Phys., Part1, 1995, 34, 3593.
88. Sengwa, R.J. and Kaur, K., Dielectric dispersion studies of poly(vinyl alcohol) in aqueous solutions, Polym. Int., 2000, 49, 1314.
89. Shinyashiki, N. and Yagihara, S., Comparison of dielectric relaxations of water mixtures of polyvinylpyrrolidone) and 1-vinyl-2-pyrrolidinone, J. Phys. Chem. B, 1999, 103, 4481.
90. Shinyashiki, N., Yagihara, S., Arita, I. and Mashimo, S., Dynamics of water in a polymer matrix studied by a microwave dielectric measurement, J. Phys. Chem. B, 1998, 102, 3249.
91. Bond, G., Moyes, R.B., Pollington, S.D. and Whan, D.A., The superheating of liquids by microwave-radiation, Chem. Ind., 1991, 686.
92. Rault, S., Gillard, A.C., Foloppe, M.P. and Robba, M., A new rearrangement under microwave-heating conditions-synthesis of cyclopenta B 1, 4 benzodiazepines and tetrahydrodibenzo B, F 1, 4 diazepines, Tetrahedron Lett., 1995, 36, 6673.
93. Chemeat, F. and Esweld, E., Chem. Eng. Technol., 2001, 7, 735.
94. Chemeat, F. and Esweld, E., ECOC-5, 2001, www.ecocexhibition2004.com.
95. Rao, K.J., Vaidhyanathan, B., Ganguli, M. and Ramakrishnan, P.A., Synthesis of inorganic solids using microwaves, Chem. Mat., 1999, 11, 882.
96. Wan, J.K.S. and Koch, T.A., Application of microwave-radiation for the synthesis of hydrogen-cyanide, Res. Chem. Intermed., 1994, 20, 29.
97. Wan, J.K.S., Microwaves and chemistry-the catalysis of an exciting marriage, Res. Chem. Intermed., 1993, 19, 147.
98. Mingos, D.M.P. and Baghurst, D.R., Applications of microwave dielectric heating effects to synthetic problems in chemistry, Chem. Soc. Rev., 1991, 20, 1.
99. Tse, M.Y., Depew, M.C. and Wan, J.K.S., Applications of high-power microwave catalysis in chemistry, Res. Chem. Intermed., 1990, 13, 221.
100. Mingos, D.M.P., Microwaves in chemical synthesis, Chem. Ind., 1994, 596.
101. Zhang, X.L., Hayward, D.O., and Mingos, D.M.P., Effects ofmicrowave dielectric heating on heterogeneous catalysis, Catalysis Lett., 2003, 88, 33.
102. Fan, X., Yuan, K., Hao, C., Li, N., Tan, G.Z., and Yu, X.D., Esterification by microwave irradiation on activated carbon, Org. Prep. Proced. Int., 2000, 32, 287.
103. Hajek, M., Microwave activation of homogeneous and heterogeneous catalytic reactions, Collect. Czech. Chem. Comm., 1997, 62, 347.
104. Tanner, D.D., Kandanarachi, P., Ding, D., Shao, H., Vizitiu, D., and Franz, J.A., The catalytic conversion of C1-Cn hydrocarbons; microwave assisted C-H' bond activation, Energy Fuel, 2000, 15, 197.
105. Abribat, B. and LeBigot, Y., Solvent-free selective etherification of hydroxyl. 2. catalytic role of polyethyleneg-lycols, Tetrahedron, 1997, 53, 2119.
106. Abribat, B., Lebigot, Y. and Gaset, A., Etherification of alcohols in the absence of solvent-catalytic function of polyethers in a solid-liquid medium, Synth. Commun., 1994, 24, 2091.
107. Abribat, B., Lebigot, Y. and Gaset, A., A simple and inexpensive method for etherification of hydroxylated polyethers in the absence of solvent, Synth. Commun., 1994, 24, 1773.
108. Berdague, P., Perez, F., Courtieu, J. and Bayle, J.P., Selective etherification of polyhydroxybenzenes using PEG-200 as solvent or cosolvent, Bull. Soc. Chim. Fr., 1993, 130, 475.
109. Blettner, C.G., Konig, W.A., Stenzel, W. and Schotten, T., Microwave-assisted aqueous Suzuki cross-coupling reactions, J. Org. Chem., 1999, 64, 3885.
110. Neumann, R. and Sasson, Y., Polyethylene glycols) as phase-transfer catalysts in the alkoxylation of halobenzenes of alkyl aryl ethers, Tetrahedron, 1983, 39, 3437.
111. Sauvagnat, B., Kulig, K., Lamaty, F., Lazaro, R. and Martinez, J., Soluble polymer supported synthesis of α-amino acid derivatives, J. Comb. Chem., 2000, 2, 134.
112. Sauvagnat, B., Lamaty, F., Lazaro, R. and Martinez, J., Polyethylene glycol) as solvent and polymer support in the microwave assisted parallel synthesis of aminoacid derivatives, Tetrahedron Lett., 2000, 41, 6371.
113. Sauvagnat, B., Lamaty, F., Lazaro, R. and Martinez, J., Polyethylene glycol (PEG) as polymeric support and phase-transfer catalyst in the soluble polymer liquid phase synthesis of α-amino esters, Tetrahedron Lett., 1998, 39, 821.
114. Totten, G.E. and Clinton, N.A., Polyethylene glycol) derivatives as phase-transfer catalysts and solvents for organic-reactions, J. Macromol. Sci., Rev. Macromol. Chem. Phys., 1988, C28, 293.
115. Totten, G.E., Clinton, N.A. and Matlock, P.L., Polyethylene glycol) and derivatives as phase transfer catalysts, J. Macromol. Sci., Rev. Macromol. Chem. Phys., 1998, C38, 77.
116. Gokel, G.W., Goli, D.M. and Schultz, R.A., Binding profiles for oligoethylene glycols and oligoethylene glycol monomethyl ethers and an assessment of their abilities to catalyze phase-transfer reactions, J. Org. Chem., 1983, 48, 2837.
117. Harris, J.M., Hundley, N.H., Shannon, T.G. and Struck, E.C., Polyethylene glycols as soluble, recoverable, phase-transfer catalysts, J. Org. Chem., 1982, 47, 4789.
118. Harris, J.M. (Ed.), Poly(ethylene glycol) Chemistry. Biotechnological and Biomedical Applications, Plenum Press, New York, 1992, p. 3.
119. Takagi, T., Appl. Polym. Sci., 1975, 19, 1774.
120. Blackwell, H.E., Out of the oil bath and into the oven-microwave-assisted combinatorial chemistry heats up, Org. Biomol. Chem., 2003, 1, 1251.
121. Kappe, C.O., High-speed combinatorial synthesis utilizing microwave irradiation, Curr. Opin. Chem. Biol., 2002, 6, 314.
122. Yang, G.C., Chen, Z.X. and Hu, C.L., Microwave-assisted polymer-supported organic reaction, Chin. J. Org. Chem., 2002, 22, 289.
123. Varma, R.S. and Dahiya, R., Microwave-assisted facile synthesis of imines and enamines using envirocat EPZG as a catalyst, Synlett, 1997, 1245.
124. Perez, R., Perez, E.R., Suarez, M., Gonzalez, L., Loupy, A. et al., Synthesis of aminotoluenesulfonamide derivatives using conventional heating or microwave-assisted methods, Org. Prep. Proced. Int., 1997, 29, 671.
125. Kidwai, M., Kumar, P., Goel, Y. and Kumar, K., Microwave assisted synthesis of 5-methyl-1, 3, 4-thiadiazol-2-ylthio/tetrazol-1-yl substituted pyrazoles, 2-azetidinones, 4-thiazolidinones, benzopyran-2-ones and 1, 3, 4-oxadiazoles, Indian. J. Chem., Sect. B, 1997, 36, 281.
126. Tierney, J., In: Advances in Productive Chemistry Development, Second Conference on Coherent Synthesis, San Diego, USA, 2002.
127. Perreux, L., Loupy, A. and Delmotte, M., Microwave effects in solvent-free ester aminolysis, Tetrahedron, 2003, 59, 2185.
128. Simoni, D., Invidiata, F.P., Manfredini, S., Ferroni, R., Lampronti, I. et al., Facile synthesis of 2-nitroalkanols by tetramethylguanidine (TMG)-catalyzed addition of primary nitroalkanes to aldehydes and alicyclic ketones, Tetrahedron Lett., 1997, 38, 2749.
129. Simoni, D., Rondanin, R., Morini, M., Baruchello, R. and Invidiata, F.P., 1, 5, 7-triazabicyclo 4.4.0 dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems, Tetrahedron Lett., 2000, 41, 1607.
130. Merriman, G., In: Advances in Productive Chemistry Development, Second Conference on Coherent Synthesis, San Diego, USA, 2002.
131. Vasudevan, A., Gentles, R., Sowin, T. and Wodka, D., In: Advances in Productive Chemistry Development, Second Conference on Coherent Synthesis, San Diego, USA, 2002.
132. Vasudevan, A., Microwave Synthesis: Chemistry at the Speed of Light, Hayes, B.L., ed., CEM Corp Publishing, 2002.
133. Crosignani, S., White, P.D. and Linclau, B., Microwave-accelerated O-alkylation of carboxylic acids with O-alkylisoureas, Org. Lett., 2002, 4, 2961.
134. Crosignani, S., White, P.D. and Linclau, B., Polymer-supported O-methylisourea: a new reagent for the O-methylation of carboxylic acids, Org. Lett., 2002, 4, 1035.
135. Westman, J., An efficient combination of microwave dielectric heating and the use of solid-supported triphenylphosphine for wittig reactions, Org. Lett., 2001, 3, 3745.
136. Nicewonger, R.B., Ditto, L., Kerr, D. and Varady, L., Synthesis of a novel, recyclable, solid-phase acylating reagent, Bioorg. Med. Chem. Lett., 2002, 12, 1799.
137. Petricci, E., Botta, M., Corelli, F. and Mugnaini, C., An improved synthesis of solid-supported reagents (SSRs) for selective acylation of amines by microwave irradiation, Tetrahedron Lett., 2002, 43, 6507.
138. Passerini, M., Formation of α-hydroxycarboxamides on treatment of an isonitrile with a carboxylic acid and an aldehyde or ketone, Gazz. Chim. Ital., 1921, 51, 126.
139. Ugi, I., Betz, W. and Fetzer, U., 1961, 94, 2814.
140. Ugi, I., Domling, A. and Werner, B., Since 1995 the new chemistry of multi-component reactions and their libraries, including their heterocyclic chemistry, J. Heterocycl. Chem., 2000, 37, 647.
141. Domling, A. and Ugi, I., The 7-component reaction, Angew. Chem., Int. Ed. Engl., 1993, 32, 563.
142. Bauer, S.M. and Armstrong, R.W., Total synthesis of Motuporin (Nodularin-V), J. Am. Chem. Soc., 1999, 121, 6355.
143. Weber, L., Illgen, K. and Ailmletter, M., Discovery of new multi component reactions with combinatorial methods, Synlett, 1999, 366.
144. Domling, A. and Ugi, I., Multi-component reactions with isocyanides, Angew. Chem., Int. Ed. Engl., 2000, 39, 3169.
145. Domling, A., The discovery of new isocyanide-based multi-component reactions, Curr. Opin. Chem. Biol., 2000, 4, 318.
146. Ley, S.V. and Taylor, S.J., A polymer-supported [1.3.2]oxazaphospholidine for the conversion of isothio-cyanates to isocyanides and their subsequent use in an Ugi reaction, Bioorg. Med. Chem. Lett., 2002, 12, 1813.
147. Rüchardt, C., Meier, M., Haaf, K., Pakusch, J., Wolber, E.K.A. et al., The isocyanide-cyanide rearrangement-mechanism and preparative applications, Angew. Chem.-Int. Ed. Engl., 1991, 30, 893.
148. Launay, D., Booth, S., Clemens, I., Merritt, A. and Bradley, M., Solid phase-mediated synthesis ofisonitriles, Tetrahedron Lett., 2002, 43, 7201.
149. Ley, S.V., Leach, A.G. and Storer, R.I., A polymer-supported thionating reagent, J. Chem. Soc., Perkin Trans. 1, 2001, 358.
150. Perregaard, J. and Lawesson, S.-O., Studies on organophosphorus compounds-XVI. On O, O-Dialkyl dithiophosphoric acids and N, N, N', N'-tetramethylthiophosphoric diamide as thiation agents: conversion of carboxamide into thiocarboxamides, alkyl dithiocarboxylates, or nitriles, Bull. Soc. Chim. Belg., 1977, 86, 321.
151. Pellletier, J.C., Khan, A., and Tang, Z., A tandem three-phase reaction for preparing secoundary amines with minimal side products, Org. Lett., 2002, 4, 26, 4611.
152. Kabza, K.G., Chapados, B.R., Gestwicki, J.E. and McGrath, J.L., Microwave-induced esterification using heterogeneous acid catalyst in a low dielectric constant medium, J. Org. Chem., 2000, 65, 1210.
153. Zu, Z.P. and Chuang, K.T., Kinetics of acetic acid esterification over ion exchange catalysts, Can. J. Chem. Eng., 1996, 74, 493.
154. Toteja, R.S.D., Jangida, B.L., Sundaresan, M. and Venkataramani, B., Water sorption isotherms and cation hydration in Dowex 50W and Amberlyst-15 ion exchange resins, Langmuir, 1997, 13, 2980.
155. Gopalakrishnan, G., Kasinath, V., Singh, N.D.P., Krishnan, V.P.S., Solomon, K.A. et al., Microwave assisted regioselective bromomethoxylation of alkenes using polymer supported bromine resins, Molecules, 2002, 7, 412.
156. Varma, R.S., Solvent-free accelerated organic syntheses using microwaves, Pure Appl. Chem., 2001, 73, 193.
157. Desai, B. and Danks, T.N., Thermal-and microwave-assisted hydrogenation of electron-deficient alkenes using a polymer-supported hydrogen donor, Tetrahedron Lett., 2001, 42, 5963.
158. Buchmeiser, M.R., Lubbad, S., Mayr, M. and Wurst, K., Access to silica-and monolithic polymer supported C-C-coupling catalysts via ROMP: applications in high-throughput screening, reactor technology and biphasic catalysis, Inorg. Chim. Acta, 2003, 345, 145.
159. Neckers, D.C., Kooistra, D.A. and Green, G.W., Polymer-protected reagents. Polystyrene-aluminium chloride, J. Am. Chem. Soc., 1972, 94, 9284.
160. Gopalakrishnan, G., Kasinath, V. and Singh, N.D.P., Microwave-assisted ketone-ketone rearrangement: an improved synthesis of 3-(4-alkoxyphenyl)-3-methylbutan-2-ones, Org. Lett., 2002, 4, 781.
161. Wipf, P. and Venkatramen, S., An improved protocol for azole synthesis with PEG-supported Burgess reagent, Tetrahedron Lett., 1996, 37, 4659.
162. Brain, C.T. and Brunton, S.A., Synthesis of 1, 3, 4-oxadiazoles using polymer-supported reagents, Synlett, 2001, 382.
163. Brain, C.T., Paul, J.M., Loong, Y. and Oakley, P.J., Novel procedure for the synthesis of 1, 3, 4-oxadiazoles from 1, 2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions, Tetrahedron Lett., 1999, 40, 3275.
164. Baxendale, I.R., Ley, S.V. and Martinelli, M., J. Med. Chem., (in press).
165. Ohberg, L. and Westman, J., One-pot three-step solution phase syntheses of thiohydantoins using microwave heating, Synlett, 2001, 1893.
166. Chen, S.T., Chiou, S.H. and Wang, K.T., Preparative scale organic-synthesis using a kitchen microwave-oven, J. Chem. Soc., Chem. Commun., 1990, 807.
167. Leskovsek, S., Plazl, I. and Koloini, T., Hydrolysis of sucrose with microwaves in a tubular flow reactor, Chem. Biochem. Eng. Q., 1996, 10, 21.
168. Plazl, I., Leskovsek, S. and Koloini, T., Hydrolysis of sucrose by conventional and microwave-heating in stirred-tank reactor, Chem. Eng. J. Biochem. Eng. J., 1995, 59, 253.
169. Plazl, I., Pipus, G. and Koloini, T., Microwave heating of the continuous flow catalytic reactor in a nonuniform electric field, AIChE J., 1997, 43, 754.
170. Hut, Y.M. and Ju, L.K., Lipase-mediated deacetylation and oligomerization of lactonic sophorolipids, Biotechnol. Prog., 2003, 19, 303.
171. Tardioli, P.W., Fernandez-Lafuente, R., Guisan, J.M. and Giordano, R.L.C., Design of new immobilized-stabilized carboxypeptidase a derivative for production of aromatic free hydrolysates of proteins, Biotechnol. Prog., 2003, 19, 565.
172. Mabrouk, P.A., The use of poly(ethylene glycol) enzymes in nonaqueous enzymology in poly(ethylene glycol), In: Chemistry and Biological Applications (ACS Symposium Series, No 680), J. Milton Harris, Samuel Zalipsky, eds., American Chemical Society Division of Polymer Chemistry, Calif. American Chemical Society Meeting 1997, San Francisco, pp 118.
173. Shock, E.L., Stability of peptides in high-temperature aqueous-solutions, Geochim. Cosmochim. Acta, 1992, 56, 3481.
174. Adams, M.W.W. and Kelly, R.M., Enzymes from microorganisms from extreme environments, Chem. Eng. News, 1995, 73, 32.
175. Carrillo-Munoz, J.-S., Bouvet, D., Eryka, G.-J., Loupy, A. and Petit, A., Microwave-promoted lipase-catalyzed reactions. Resolution of (+/-)-1-phenylethanol, J. Org. Chem., 1996, 61, 7746.
176. GeloPujic, M., GuibeJampel, E., Loupy, A. and Trincone, A., Enzymatic glycosidation in dry media under microwave irradiation, J. Chem. Soc., Perkin Trans. 1, 1997, 1001.
177. GeloPujic, M., GuibeJampel, E., Loupy, A., Galema, S.A. and Mathe, D., Lipase-catalysed esterification of some alpha-d-glucopyranosides in dry media under focused microwave irradiation, J. Chem. Soc., Perkin Trans. 1, 1996, 2777.
178. Rao, N.S., Agarwal, S.K., Chauhan, V.K., Bhatia, D., Sharma, A.K. et al., Microwave-assisted spectrophotometry estimation of polymer-supported functional groups using a universal reagent, Anal. Chim. Acta, 2000, 405, 247.
179. Baxendale, I.R., Ley, S.V. and Piutti, C., Total Synthesis of the Amaryllidaceae Alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions, Angew. Chem., Int. Ed. Engl., 2002, 41, 2194.
180. Baxendale, I.R., Ley, S.V., Nessi, M. and Piutti, C., Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents, Tetrahedron, 2002, 58, 6285.
181. Olah, G.A., Yamato, T., Iyer, P.S. and Prakash, G.K.S., Catalysis by solid superacids. 20. Nafion-H catalyzed reductive cleavage of acetals and ketals to ethers with triethylsilane, J. Org. Chem., 1986, 51, 2826.
182. Dallinger, D., Gorobets, N.Y. and Kappe, C.O., High-throughput synthesis of N3-acylated dihydropyrim-idines combining microwave-assisted synthesis and scavenging techniques, Org. Lett., 2003, 5, 1205.