An unusual Mannich type reaction of tertiary aromatic amines in aqueous micelles

Tetrahedron Letters

Volumn 49, Issue 38, 2008, Pages 5471-5474

  Kumar, Atul ^a   Maurya, Ram Awatar ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

1,3 Dicarbonyl compounds; Aqueous micelles; Aza quinone methide; Boric acid; Tertiary aromatic amines; Unusual Mannich type reaction

Indexed keywords

1,3 DICARBONYL DERIVATIVE; ALIPHATIC AMINE; AROMATIC AMINE; BORIC ACID; CARBONYL DERIVATIVE; FORMALDEHYDE; N (4 METHYLENECYCLOHEXA 2,5 DIENYLIDENE)ALKYLAMINIUM;

ARTICLE; CATALYST; DECARBOXYLATION; MANNICH REACTION; MICELLE; QUANTUM YIELD;

EID: 48549088704     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.019     Document Type: Article

References (20)

1. Verkade J.M.M., van Hemert L.J.C., Quaedflieg P.J.L.M., and Rutjes F.P.J.T. Chem. Soc. Rev. 37 (2008) 29
2. Mukherjee S., Yang J.W., Hoffmann S., and List B. Chem. Rev. 107 (2007) 5471
3. Takahashi H., Hashimoto Y., and Nagasawa K. Heterocycles 55 (2001) 2305
4. Takahashi H., Kashiwa N., Kobayashi H., Hashimoto Y., and Nagasawa K. Tetrahedron Lett. 43 (2002) 5751
5. Takahashi H., Kashiwa N., Hashimoto Y., and Nagasawa K. Tetrahedron Lett. 43 (2002) 2935
6. Chaudhuri M.K., Hussain S., Kantam M.L., and Neelima B. Tetrahedron Lett. 46 (2005) 8329
7. Chaudhuri M.K., and Hussain S. J. Mol. Catal. A: Chem. 269 (2007) 214
8. Tu S., Fang F., Miao C., Jiang H., Feng Y., Shi D., and Wang X. Tetrahedron Lett. 44 (2003) 6153
9. Delbecq P., Celerier J.-P., and Lhommet G. Tetrahedron Lett. 31 (1990) 4873
10. Kondaiah G.C.M., Reddy L.A., Babu K.S., Gurav V.M., Huge K.G., Bandichhor R., Reddy P.P., Bhattacharya A., and Anand R.V. Tetrahedron Lett. 49 (2008) 106
11. Li C.-J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), Wiley, New York
12. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic and Professional, London
13. Li C.-J. Chem. Rev. 105 (2005) 3095
14. Li C.-J., and Chen L. Chem. Soc. Rev. 35 (2006) 68
15. In: Lindstrom U.M. (Ed). Organic Reactions in Water (2007), Blackwell Publishing, Oxford
16. Lindstrom U.M., and Andersson F. Angew. Chem., Int. Ed. 45 (2006) 548
17. Pirrung M.C. Chem. Eur. J. 12 (2006) 1312
18. Otto S., and Engberts J.B.F.N. Org. Biomol. Chem. 1 (2003) 2809
19. General experimental procedure for the unusual Mannich type reaction: In a 25 ml round-bottomed flask, N,N-dimethylaniline (0.121 g, 1 mmol), 37% aqueous formaldehyde (0.081 ml, 1 mmol), ethyl acetoacetate (0.130 g, 1 mmol), boric acid (0.013 g, 20 mol %) and SDS-water (1.5 ml, c = 0.1 g/ml) were taken. The reaction mixture was refluxed for half an hour. The reaction was followed by TLC monitoring. After completion, the reaction mixture was diluted with 25 ml water and extracted with ethyl acetate (25 × 2). The organic layer was dried over sodium sulfate and concentrated to give a crude. The crude was subjected to column chromatography to yield compound 7a (0.22 g, 84%).
20. 2: C, 80.27; H, 8.72; N, 11.01. Found: C, 80.20; H, 8.66; N, 11.12.