LaCl3Á7H2O as an Efficient Catalyst
899
Scheme 3 The possible
mechanism for three-component
one-pot reaction leading to poly
substituted piperidine
White yellow solid; melting point: 192–194 °C: IR
(KBr): 3250, 3024, 2949, 2867, 1815, 1661, 1606, 1504,
1449, 1375, 1321, 1245, 1183, 1070, 978, 920, 748,
646 cm-1: H1NMR (400 MHz, CDCl3)TM ppm: 2.78–2.74
(d, J = 14.8 Hz, 1H), 2.89–2.84 (dd, J = 30.4, 5.6 Hz,
1H), 3.93 (s, 3H), 5.15(s, 1H), 6.29–6.26 (d, J = 7.6 Hz,
2H), 6.45 (s, 1H), 6.53–6.51 (d, J = 8.4 Hz, 2H),
6.61–6.58 (t, J = 7.2 Hz, 1H), 7.33–7.03 (m, 15H), 10.25
(br s, 1H, NH); C13NMR (100 MHz, CDCl3)TM ppm: 33.6,
51.0, 55.1, 58.2, 97.9, 112.9, 116.2, 125.8, 125.9, 126.4,
126.4, 126.6, 127.2, 128.3, 128.7, 128.9, 128.9, 137.8,
142.7, 143.9, 146.9, 156.3, 168.6;
References
1. Koukabi N, Kolvari E, Khazaei A, Zolfigol MA, Shaghasemic-
Shaghasemi B, Khavasid HR (2011) Chem Commun 47:9230
2. Ghandi M, Jamea AH (2011) Tetrahedron Lett 52:4005
3. Wu H, Lin W, Wan Y, Xin H, Shi D, Shi Y, Yuan R, Bo R, Yin
W (2010) J Comb Chem 12:31
4. Urushima T, Sakamoto D, Ishikawa H, Hayashi Y (2010) Org
Lett 12:4588
5. Chen Y, Zhong C, Petersen JL, Akhmedov NG, Shi X (2009) Org
Lett 11:2333
6. Xu J, Wei J, Bian L, Zhang J, Chen J, Deng H, Wu X, Zhang H,
Cao W (2011) Chem Commun 47:3607
7. Jia XD, Wang XE, Yang CX, Huo CD, Wang WJ, Ren Y, Wang
XC (2010) Org Lett 12:732
8. Barber DM, Sanganee H, Dixon DJ (2011) Chem Commun
47:4379
9. Watson PS, Jiang B, Scott B (2000) Org Lett 2:3679
10. Imamura S, Nishikawa Y, Ichikawa T, Hattori T, Matsushita Y,
Hashiguchi S, Kanzaki N, Iizawa Y, Baba M, Sugihara Y (2005)
Bioorg Med Chem 13:397
11. Weis R, Schweiger K, Faist J, Rajkovic E, Kungl AJ, Fabian
WMF, Schunack W, Seebacher W (2008) Bioorg Med Chem
16:10326
12. Ishikawa M, Furuuchi T, Yamauchi M, Yokoyama F, Kakui N,
Sato Y (2010) Bioorg Med Chem 18:5441
13. Zhang J, Zhang P, Liu X, Fang K, Lin G (2007) Bioorg Med
Chem Lett 17:3769
14. Srinivas C, Kumar CNSP, Raju BC, Rao VJ, Naidu VGM, Ra-
makrishna S, Diwan PV (2009) Bioorg Med Chem Lett 19:5915
15. Davis FA, Chao B, Rao A (2001) Org Lett 3:3169
16. Arena G, Zill N, Salvadori J, Girard N, Mann A, Taddei M (2011)
Org Lett 13:2294
17. Jarvis SBD, Charette AB (2011) Org Lett 13:3830
18. Ragoussi ME, Walker SM, Piccanello A, Kariuki BM, Horton
PN, Spencer N, Snaith JS (2010) J Org Chem 75:7347
19. Sun J, Sun Y, Xia EY, Yan CG (2011) ACS Comb Sci 13:436
4 Conclusion
In conclusion, we have developed a one-pot three-com-
ponent intramolecular aza Diels–Alder reaction of alde-
hydes, aniline and 1,3-dicarbonyl compounds in the
presence of 10 mol% of LaCl3Á7H2O in MeOH as an
efficient catalyst. The main feature of this strategy includes
easy work up, mild reaction conditions, good yields and
high atom economy. The current methodology is attractive
for the preparation of a wide variety of biologically active
highly functionalized piperidines.
Acknowledgments Umamahesh B and Sathesh V express their
thanks to VIT management for providing financial support through
research associateship. The authors express their gratitude to Dr. T. N.
Guru Row, IISc, Bangalore and G. Sekar, IIT, Madras, India for
crystal data.
123