Efficient large scale microwave assisted Mannich reactions using substituted acetophenones

Molecular Diversity

Volumn 7, Issue 2-4, 2003, Pages 145-152

  Lehmann, Fredrik ^a   Pilotti, Åke ^b,c   Luthman, Kristina ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b Personal Chemistry   (Sweden)

^c STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Large scale; Mannich reaction; Microwave chemistry; Substituted acetophenones

Indexed keywords

ACETOPHENONE; AMINE; MANNICH BASE; PARAFORMALDEHYDE; SOLVENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; MANNICH REACTION; MICROWAVE RADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; TEMPERATURE DEPENDENCE;

ACETOPHENONES; AMINES; CHEMISTRY, ORGANIC; COMBINATORIAL CHEMISTRY TECHNIQUES; HEATING; MAGNETIC RESONANCE SPECTROSCOPY; MICROWAVES; SOLVENTS; TEMPERATURE; TIME FACTORS;

EID: 0347635266     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006809.48284.ed     Document Type: Article

References (34)

1. Mannich, C. and Abdullah, S. M., The bases formed from acetophenone, formaldehyde and ammonium chloride, Ber. 68 (1935) 113-120.
2. Arend, M., Westermann, E. and Risch, N., What does Carl Mannich have to do with frogs?, Angew. Chem. Int. Ed., 37 (1998) 1044-1070.
3. These reactions are often run in HCl at high temperatures; see e.g. Bryant, J. A., Helgeson, R. C., Knobler, C. B., de-Grandpre, M. P. and Cram, D. J., Host-Guest complexation. 53. Functional group preorganized in hemispherands for binding alkali metal and ammonium cations, J. Org. Chem., 55 (1990) 4622-4634.
4. Lidström, P., Thiemey, J., Whatey, B. and Westman, J., Microwave assisted organic synthesis - A review, Tetrahedron, 57 (2001) 9225-9283.
5. Gadhwal, S., Baruah, M., Prajapati, D. and Sandhu, J. S., Microwave assisted regioselective synthesis of β-aminoketones via the Mannich reaction, Synlett, 3 (2000) 341-342.
6. Microwave assisted aminoalkylation reactions have also been reported. For reactions of terminal alkynes on alumina, see: Sharifi, A., Farhangain, H., Mohsenzadeh, F. and Naimi-Jamal, M. R., Microwave assisted Mannich reaction on terminal alkynes on alumina, Monatsh. Chem., 133 (2002) 199-204. For microwave assisted aminoalkylations of phenols and indoles, see: Sharifi, A., Mirzaei, M. and Naimi-Jamal, M. R., Solvent free aminoalkylation of phenols and indoles assisted by microwave irradiation, Monatsh. Chem., 132 (2001) 875-880. For microwave enhanced condensations on CuI-doped alumina, see Kabalka, G. W., Wang, L. and Pagni, R. M., A microwave-enhanced, solventless Mannich condensation on CuI-doped alumina, Synlett, 5 (2001) 676-678. For microwave assisted aminoalkylation of electron-rich compounds, see: Mojtahedi, M. M., Sharifi, A., Mohsenzadeh, F. and Saidi, M. R., Microwave-assisted aminomethylation of electronrich compounds under solvent-free condition, Synth. Commun., 30 (2000) 69-72.
7. Microwave assisted aminoalkylation reactions have also been reported. For reactions of terminal alkynes on alumina, see: Sharifi, A., Farhangain, H., Mohsenzadeh, F. and Naimi-Jamal, M. R., Microwave assisted Mannich reaction on terminal alkynes on alumina, Monatsh. Chem., 133 (2002) 199-204. For microwave assisted aminoalkylations of phenols and indoles, see: Sharifi, A., Mirzaei, M. and Naimi-Jamal, M. R., Solvent free aminoalkylation of phenols and indoles assisted by microwave irradiation, Monatsh. Chem., 132 (2001) 875-880. For microwave enhanced condensations on CuI-doped alumina, see Kabalka, G. W., Wang, L. and Pagni, R. M., A microwave-enhanced, solventless Mannich condensation on CuI-doped alumina, Synlett, 5 (2001) 676-678. For microwave assisted aminoalkylation of electron-rich compounds, see: Mojtahedi, M. M., Sharifi, A., Mohsenzadeh, F. and Saidi, M. R., Microwave-assisted aminomethylation of electronrich compounds under solvent-free condition, Synth. Commun., 30 (2000) 69-72.
8. Microwave assisted aminoalkylation reactions have also been reported. For reactions of terminal alkynes on alumina, see: Sharifi, A., Farhangain, H., Mohsenzadeh, F. and Naimi-Jamal, M. R., Microwave assisted Mannich reaction on terminal alkynes on alumina, Monatsh. Chem., 133 (2002) 199-204. For microwave assisted aminoalkylations of phenols and indoles, see: Sharifi, A., Mirzaei, M. and Naimi-Jamal, M. R., Solvent free aminoalkylation of phenols and indoles assisted by microwave irradiation, Monatsh. Chem., 132 (2001) 875-880. For microwave enhanced condensations on CuI-doped alumina, see Kabalka, G. W., Wang, L. and Pagni, R. M., A microwave-enhanced, solventless Mannich condensation on CuI-doped alumina, Synlett, 5 (2001) 676-678. For microwave assisted aminoalkylation of electron-rich compounds, see: Mojtahedi, M. M., Sharifi, A., Mohsenzadeh, F. and Saidi, M. R., Microwave-assisted aminomethylation of electronrich compounds under solvent-free condition, Synth. Commun., 30 (2000) 69-72.
9. Microwave assisted aminoalkylation reactions have also been reported. For reactions of terminal alkynes on alumina, see: Sharifi, A., Farhangain, H., Mohsenzadeh, F. and Naimi-Jamal, M. R., Microwave assisted Mannich reaction on terminal alkynes on alumina, Monatsh. Chem., 133 (2002) 199-204. For microwave assisted aminoalkylations of phenols and indoles, see: Sharifi, A., Mirzaei, M. and Naimi-Jamal, M. R., Solvent free aminoalkylation of phenols and indoles assisted by microwave irradiation, Monatsh. Chem., 132 (2001) 875-880. For microwave enhanced condensations on CuI-doped alumina, see Kabalka, G. W., Wang, L. and Pagni, R. M., A microwave-enhanced, solventless Mannich condensation on CuI-doped alumina, Synlett, 5 (2001) 676-678. For microwave assisted aminoalkylation of electron-rich compounds, see: Mojtahedi, M. M., Sharifi, A., Mohsenzadeh, F. and Saidi, M. R., Microwave-assisted aminomethylation of electronrich compounds under solvent-free condition, Synth. Commun., 30 (2000) 69-72.
10. Gabriel, C., Gabriel, S., Grant, E. H., Halstead, B. S. J. and Mingos, D. M. P., Dielectric parameters relevant to microwave dielectric heating, Chem. Soc. Rev., 27 (1998) 213-221.
11. Burpitt, B. E., Crawford, L. P., Davies, B. J., Mistry, J., Mitchell, M. B. and Pancholli, K. D., 6-(Substituted phenyl)-5-methyl-4,5-dihydro-pyridazin-3(2H)-ones of medicinal interest. The synthesis of SK&F 94836 and SK&F 95654, J. Heterocycl. Chem., 25 (1988) 1689-1695.
12. Girreser, U., Heber, D. and Schuett, M., A facile one-pot synthesis of 1-aryl-2-(dimethylaminomethyl)prop-2-en-1-ones from aryl methyl ketones, Synthesis, 5 (1998) 715-717.
13. Handa, S., Jones, K. and Newton, C. G., Synthetic studies on morphine-based analgesics. Intramolecular Diels-Alder approach to 4a-aryldecahydroisoquinolines, J. Chem. Soc., Perkin Trans. 1, 12 (1995) 1623-1633.
14. Clark, J. H. and Cork, D. G., Synthesis of 1,4-diketones by fluoride-catalysed Michel addition and supported permanganate oxidation, J. Chem. Soc., Chem. Commun., 11 (1982) 635-636.
15. Meindl, W., Laske, R. and Boem, M., Tumor-inhibiting β-amino ketones. Arch. Pharm. 320 (8), (1987), 730-737. Coates, W. J., Prain, H. D., Reeves, M. L. and Warrington, B. H., 1,4-Bis(3-oxo-2,3-dihydropyridazin-6-yl)benzene analogues: Potent phosphodiesterase inhibitors and inodilators, J. Med. Chem., 33 (1990) 1735-1741.
16. Meindl, W., Laske, R. and Boem, M., Tumor-inhibiting β-amino ketones. Arch. Pharm. 320 (8), (1987), 730-737. Coates, W. J., Prain, H. D., Reeves, M. L. and Warrington, B. H., 1,4-Bis(3-oxo-2,3-dihydropyridazin-6-yl)benzene analogues: Potent phosphodiesterase inhibitors and inodilators, J. Med. Chem., 33 (1990) 1735-1741.
17. Lindström, U. M., Olofsson, B. and Somfai, P., Microwave-assisted aminolysis of vinylepoxides, Tetrahedron Lett., 40 (1999) 9273-9276
18. (a) Microwave-Enhanced Chemistry, Kingston, H. M. and Haswell, S. J. (eds), American Chemical Society, Washington, DC, 1997.
19. (b) Microwaves in Organic Synthesis, Loupy, A. (ed.), Wiley-VCH, Weinheim, 2002.
20. (c) Microwave-Assisted Organic Synthesis, Lidström, P. and Tierney, J. P. (eds), Blackwell Publishing, Oxford, 2004.
21. For multimode batch reactors, see: Raner, K. D., Strauss, C. R., Trainor, R. W. and Thorn, J. S., A new microwave reactor for batchwise organic synthesis, J. Org. Chem., 60 (1995) 2456-2460.
22. For monomode batch reactors, see: (a) Perio, B., Dozias, M.-J. and Hamelin, J., Ecofriendly fast batch synthesis of dioxolanes, dithiolanes, and oxathiolanes without solvent under microwave irradiation, Org. Process Res. Dev., 2 (1998) 428-430.
23. (b) Cléophax, J., Liagre, M., Loupy, A. and Petit, A., Application of focused microwaves to the scale-up of solvent-free organic reactions, Org. Process Res. Dev., 4 (2000) 498-504.
24. For continuous flow reactors, see: (a) Cablewski, T., Faux, A. F. and Strauss, C. R., Development and application of a continuous microwave reactor for organic synthesis, J. Org. Chem., 59 (1994) 3408-3412.
25. (b) Kazba, K., 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., 65 (2000) 1210-1214.
26. (c) Khadilkar, B. M., and Madyar, V. R., Scaling up of dihydropyridine ester synthesis by using aqueous hydrotrope solutions in a continuous microwave reactor, Org. Process Res. Dev., 5 (2001) 452-455.
27. (d) Esveld, E., Chemat, F. and Van Haveren, J., Pilot scale continuous microwave dry-media reactor - Part I: Design and modeling, Chem. Eng. Technol., 23 (2000) 279-283.
28. (e) Esveld, E., Chemat, F. and Van Haveren, J., Pilot scale continuous microwave dry-media reactor - Part II: Application to waxy esters production, Chem. Eng. Technol., 23 (2000) 429-435.
29. (f) Hayes, B. L., Collins, M. J., Collins Jr., J. M., Abstracts of Papers, 225th ACS National Meeting, New Orleans, LA, United States, 23-27 March 2003, ORGN-053.
30. (g) Shieh, W.-C., Dell, S. and Repic, O., Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate, Tetrahedron Lett., 43 (2002) 5607-5609.
31. Hoegberg, T., Ulff, B. and Renyi, A. L., Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake, J. Med. Chem., 24 (1981) 1499-1507.
32. Carter, R. H., Garson, M. J., Hill, R. A., Staunton, J. and Sunter, D. C., The synthesis of indan-1-ones and isocoumarines, J. Chem. Soc., Perkin Trans. 1, (1981) 471-479.
33. Huang, Y. and Hall, I. H., Hypolipidemic effects of α-, β-, and y-alkylaminophenone analogs in rodents, Eur. J. Med. Chem., 31 (1996) 281-290.
34. Wang, M. D. and Alper, H., Regioselective synthesis of piperidones by metal-catalysed ring expansion-carbonylation reactions. Remarkable cobalt and/ or ruthenium carbonyl catalyzed rearrangement and cyclization reactions, J. Am. Chem. Soc., 114 (1992) 7018-7024.