Facile and green method for the synthesis of-aminoketone derivatives in aqueous media

Synthetic Communications

Volumn 40, Issue 7, 2010, Pages 964-972

  Wang, Xiang Shan ^a,b   Zhou, Jie ^a   Yang, Ke ^a   Li, Qing ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

1,2 diphenylethanone; 2 naphthalenamine; Aqueous media; TEBAC

Indexed keywords

1,2 DIPHENYL 3 (3 FLUOROPHENYL) 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 1,2 DIPHENYL 3 (3,4 METHYLENEDIOXYLPHENYL) 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 1,2 DIPHENYL 3 (4 FLUOROPHENYL) 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 1,2 DIPHENYL 3 (4 METHOXYPHENYL) 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 1,2 DIPHENYL 3 (4 METHYLPHENYL) 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 1,2 DIPHENYL 3 (NAPHTHALEN 2 YLAMINO) 3 (3 NITROPHENYL)PROPAN 1 ONE; 1,2 DIPHENYLETHANONE; 2 NAPHTHALENAMINE; 3 (3 BROMOPHENYL) 1,2 DIPHENYL 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 3 (3 CHLOROPHENYL) 1,2 DIPHENYL 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 3 (3,4 DICHLOROPHENYL) 1,2 DIPHENYL 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 3 (4 BROMOPHENYL) 1,2 DIPHENYL 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 3 (4 CHLOROPHENYL) 1,2 DIPHENYL 3 (NAPHTHALEN 2 YLAMINO)PROPAN 1 ONE; 3 ARYL 3 (NAPHTHALEN 2 YLAMINO) 1,2 DIPHENYLPROPAN 1 ONE DERIVATIVE; ALDEHYDE; AMINOKETONE; AMMONIUM CHLORIDE; NAPHTHALENE DERIVATIVE; TRIETHYLBENZYLAMMONIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CONTROLLED STUDY; DRUG SYNTHESIS;

EID: 77749298091     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903029859     Document Type: Article

References (35)

1. (a) Knapp, S. Synthesis of complex nucleoside antibiotics. Chem. Rev. 1995, 95, 1859-1876;.
2. (b) Wang, Y.-F; Izawa, T; Kobayashi, S; Ohno, M. Stereocontrolled synthesis of (\+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction. J. Am. Chem. Soc. 1982, 104, 6465-6466;.
3. (c) Seebach, D; Matthews, J. L. b-Peptides: A surprise at every turn. J. Chem. Soc., Chem. Commun. 1997, 2015-2022.
4. (a) Hulst, R; Heres, H; Peper, N. C. M. W; Kellogg, R. M. Synthesis and application of new chiral ligands for the asymmetric borane reduction of prochiral ketones. Tetrahedron: Asymmetry 1996, 7, 1373-1384;.
5. (b) Li, X; Yeung, C.-H; Chan, A. S. C; Yang, T.-K. New 1,3-amino alcohols derived from ketopinic acid and their application in catalytic enantioselective reduction of prochiral ketones. Tetrahedron: Asymmetry 1999, 10, 759-763.
6. (a) Welch, W. M; Kraska, A. R; Sarges, R; Koe, B. K. Nontricyclic antidepressant agents derived from cis-and trans-1-amino-4-aryltetralins. J. Med. Chem. 1984, 27, 1508-1515;.
7. (b) Chen, C; Reamer, R. A. Efficient enantioselective synthesis of sertraline, a potent antidepressant, via a novel intramolecular nucleophilic addition to imine. Org. Lett. 1999, 1, 293-294;.
8. (c) Corey, E. J; Gant, T. G. A catalytic enantioselective synthetic route to the important antidepressant sertraline. Tetrahedron Lett. 1994, 35, 5373-5376.
9. (a) Enders, D; Muller, S. F; Raabe, G. Enantioselective synthesis of b-amino sulfones by aza-Michael addition to alkenyl sulfones. Angew. Chem., Int. Ed. 1999, 38, 195-197;.
10. (b) Kochi, T; Tang, T; Ellman, J. A. Development and application of a new general method for the asymmetric synthesis of syn-and anti-1,3-amino alcohols. J. Am. Chem. Soc. 2003, 125, 11276-11282;.
11. (c) Murai, T; Sano, H; Kawai, H; Aso, H; Shibahara, F. N-Thioacyl 1,3-amino alcohols: synthesis via ring-opening of oxiranes with thioamide dianions and applications as key intermediates leading to stereochemically defined 5,6-dihydro-4H-1,3-oxazines and 1,3-amino alcohols. J. Org. Chem. 2005, 70, 8148-8153;.
12. (d) Kochi, T; Tang, T. P; Ellman, J. A. Asymmetric synthesis of syn-and anti-1,3-amino alcohols. J. Am. Chem. Soc. 2002, 124, 6518-6519.
13. Kantevari, S; Vuppalapati, S. V. N; Nagarapu, L. Montmorillonite K10-catalyzed efficient synthesis of amidoalkyl naphthols under solvent-free conditions. Catal. Commun. 2007, 8, 1857-1862.
14. Selvam, N. P; Perumal, P. T. A new synthesis of acetamido phenols promoted by Ce(SO4)2. Tetrahedron Lett. 2006, 47, 7481-7483.
15. Das, B; Laxminarayana, K; Ravikanth, B; Rao, B. R. Iodine-catalyzed preparation of amidoalkyl naphthols in solution and under solvent-free conditions. J. Mol. Catal. A: Chem. 2007, 261, 180-183.
16. 2O): A mild and efficient reusable catalyst for the synthesis of amidoalkyl naphthols in solution and under solvent-free conditions. Catal. Commun. 2007, 8, 1729-1734. (Pubitemid 47419482)
17. Khodaei, M. M; Khosropour, A. R; Moghanian, H. A simple and efficient procedure for the synthesis of amidoalkyl naphthols by p-TSA in solution or under solvent-free conditions. Synlett 2006, 916-920.
18. Patil, S. B; Singh, P. R; Surpur, M. P; Samant, S. D. Ultrasound-promoted synthesis of 1-amidoalkyl-2-naphthols via a three-component condensation of 2-naphthol, ureas/ amides, and aldehydes, catalyzed by sulfamic acid under ambient conditions. Ultrason. Sonochem. 2007, 14, 515-518.
19. Patil, S. B; Singh, P. R; Surpur, M. P; Samant, S. D. Cation-exchanged resins: Efficient heterogeneous catalysts for facile synthesis of 1-amidoalkyl-2-naphthols from one-pot, three-component condensations of amides/ureas, aldehydes, and 2-naphthol. Synth. Commun. 2007, 37, 1659-1664.
20. Srihari, G; Nagaraju, M; Murthy, M. M. Solvent-free one-pot synthesis of amidoalkyl naphthols catalyzed by silica sulfuric acid. Helv. Chim. Acta 2007, 90, 1497-1504.
21. (a) Spassov, S. L; Panajotova, B; Spassov, A. Proton NMR spectra and stereochemistry of diastereomeric aryl-substituted (5-amino ketones. J. Prakt. Chem. 1980, 322, 701-703;
22. Chem. Abstr. 1980, 94, 64982.
23. (b) Panaiotova, B; Pencheva, B; Spasov, A. Behavior of aryl-subtituted (5-amino ketones with respect to some reagents. Doklady Bolgarskoi Akademii Nauk. 1973, 26, 905-908;
24. Chem. Abstr. 1973, 80, 70481h.
25. (a) Jin, T.-S; Zhang, J.-S; Guo, T.-T; Wang, A.-Q; Li, T.-S. One-pot clean synthesis of 1,8-dioxo-decahydroacridines catalyzed by /j-dodecylbenezenesulfonic acid in aqueous media. Synthesis 2004, 2001-2005;.
26. 2 chiral diamine in aqueous media. Chem.\Eur. J. 2006,12, 1205-1215;.
27. (c) Zhang, Z; Zha, Z; Gan, C; Pan, C; Zhou, Y; Wang, Z; Zhou, M. Catalysis and regioselectivity of the aqueous Heck reaction by Pd(0) nanoparticles under ultrasonic irradiation. J. Org. Chem. 2006, 71, 4339-4342;.
28. (d) Hamamoto, H; Kudoh, M; Takahashi, H; Ikegami, S. Novel use of cross-linked poly(N-isopropylacrylamide) gel for organic reactions in aqueous media. Org. Lett. 2006, 8, 4015-4018;.
29. (f) Yang, J.-H; Li, J.-T; Zhao, J.-L; Li, T.-S. Pinacol coupling reaction of aromatic aldehydes mediated by Zn in acid aqueous media under ultrasound irradiation. Synth. Commun. 2004, 34, 993-1000;.
30. (g) Balalaie, S; Nikoo, S; Haddadi, S. Aqueous-phase synthesis of 2-aminothiazole and 2-iminothiazolidine derivatives catalyzed by diammonium hydrogen phosphate and DABCO. Synth. Commun. 2008, 38, 2521-2528.
31. (a) Wang, X. S; Zhang, M. M; Zeng, Z. S; Shi, D. Q; Tu, S. J; Wei, X. Y; Zong, Z. M. A simple and clean procedure for the synthesis of polyhydroarcidine and quinoline derivatives: Reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium. Tetrahedron Lett. 2005, 46, 7169-7173;.
32. (b) Wang, X. S; Zhang, M. M; Li, Q; Yao, C. S; Tu, S. J. An unexpected triethylbenzylammonium chloride-catalyzed ring-opening of 2-pyrones in the synthesis of 1-arylbenzo[f]quinoline-2-carboxmide derivatives in aqueous media. Synlett 2007, 3141-3144;.
33. (c) Wang, X. S; Zhang, M. M; Jiang, H; Li, Q; Shi, D. Q; Tu, S. J. Unexpected spiro-benzoquinolines in the reaction of N-arylidenenaphthalen-2- amine, arylaldehyde, and 1,3-dimethylbarbituric acid in water. Chem. Lett. 2007,36, 450-451;.
34. (d) Wang, X. S; Zhang, M. M; Shi, D. Q; Tu, S. J; Wei, X. Y; Zong, Z. M. A new synthesis method for benzo[f]quinolin-3-carbonyl urea and thiourea derivatives in aqueous media catalyzed by TEBAC. J. Heterocycl. Chem. 2007, 36, 441-447;.
35. +][BFJ]: Reactions of arylaldehyde, 3-arylamino-5,5-dimethylcyclohex- 2-enone, and active methylene compounds. Tetrahedron 2007, 63, 4439-4449