Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brønsted Acid-Surfactant-Combined Catalyst in Water

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1965-1967

  Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001549125     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991113u     Document Type: Article

References (27)

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4. (b) Mixed Surfactant Systems; Holland, P. M., Rubingh, D. N., Eds.; American Chemical Society: Washington, DC, 1992.
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10. (f) Manabe, K.; Mori, Y.; Nagayama, S.; Odashima, K.; Kobayashi, S. Inorg. Chim. Acta, in press.
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14. (c) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 703.
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16. (e) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
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20. HCl-catalyzed three-component Mannich-type reactions of aldehydes, amines, and ketones in EtOH have been reported. (a) Blatt, A. H.; Gross, N. J. Org. Chem. 1964, 29, 3306.
21. (b) Yi, L.; Zou, J.; Lei, H.; Lin, X.; Zhang, M. Org. Prep. Proced. Int. 1991, 23, 673.
22. Multiple-component reactions, which can produce a diversity of compounds, provide one of the most efficient methods for the combinatorial synthesis of compound libraries. For example, see: Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
23. Dodecylbenzenesulfonic acid (soft type) was purchased from Tokyo Kasei Kogyo Co., Ltd., and used without further purification. This is a mixture of several linear alkylbenzenesulfonic acids. Its molecular weight was regarded as 326.50.
24. 6a have been reported earlier. The spectral data for the other Mannich adducts are included in the Supporting Information.
25. Koslov, N. S.; Vorob'ev̇a, G. V. Vestsi Akad. Nauk Belarus SSR, Ser. Khim. Nauk 1968, 107.
26. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
27. 3 solution (5 mL) and brine (5 mL) were added, and the mixture was extracted with ethyl acetate. Purification by silica gel chromatography gave the desired product. Ten-mmol-scale reactions were also carried out without any difficulties. For example, the reaction of benzaldehyde (10 mmol), aniline (10 mmol), and acetophenone (10 mmol) in the presence of 10 mol % of DBSA afforded the product in 82% yield (24 h).