Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals

Tetrahedron

Volumn 71, Issue 1, 2015, Pages 102-108

  Zakusilo, Dmitry N ^a   Ryabukhin, Dmitry S ^b   Boyarskaya, Irina A ^b   Yuzikhin, Oleg S ^a   Vasilyev, Aleksander V ^a,b  

^a SAINT PETERSBURG STATE FOREST TECHNICAL UNIVERSITY   (Russian Federation)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

3,3 Diarylpropylamines; Cinnamides; DFT calculations; Hydroarylation; Superacids

Indexed keywords

3,3 DIARYLPROPYLAMINE; CARBONYL DERIVATIVE; CHEMICALS AND DRUGS; CINNAMIDE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; COVALENT BOND; DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; HYDROARYLATION; SYNTHESIS;

EID: 84918823761     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.11.033     Document Type: Article

References (37)

1. A. Kleeman, and J. Engel Pharmazeutische Wirkstoff 1987 Thieme Stuttgart, Germany
2. A. Giringauz Medicinal Chemistry 1997 Wiley-VCH New York, NY
3. F.E.R. Simons, E.M. Fritch, and K. Simons J. Allergy Clin. Immunol. 70 1982 458 464
4. H.M. Piper, J.F. Hutler, and P.G. Spieckerman Arzneim. Forsch. 35 1985 1495 1498
5. H. Certa, and G. Blashke Arch. Pharm. 323 1990 744 747
6. Z. Chen, W.S. Miller, S. Shan, and K.J. Valenzano Bioorg. Med. Chem. Lett. 13 2003 3247 3252
7. R.R. Goehring, J.F. Whitehead, K. Brown, K. Islam, X. Wen, X. Zhou, Z. Chen, K.J. Valenzano, W.S. Miller, S. Shan, and D.J. Kyle Bioorg. Med. Chem. Lett. 14 2004 5045 5050
8. J.N. Burrows, J.G. Cumming, S.M. Fillery, G.A. Hamlin, J.A. Hudson, R.J. Jackson, S. McLaughlin, and J.S. Shaw Bioorg. Med. Chem. Lett. 15 2005 25 28
9. C. Botteghi, L. Cazzolato, M. Marchetti, and S. Paganelli J. Org. Chem. 60 1995 6612 6615
10. T. Rische, and P. Eilbracht Tetrahedron 55 1999 1915 1920
11. M. Ahmed, C. Buch, L. Routaboul, R. Jackstell, H. Klein, A. Spannenberg, and M. Beller Chem. - Eur. J. 13 2007 1594 1601
12. S. Li, K. Huang, J. Zhang, W. Wu, and X. Zhang Org. Lett. 15 2013 1036 1039
13. G.H. Baek, S.J. Cho, Y.S. Jung, C.-M. Seong, C.-W. Lee, and N.-S. Park Bull. Korean Chem. Soc. 20 1999 232 236
14. J. Lee, S.-U. Kang, J.-O. Lim, H.-K. Choi, M.-K. Jin, A. Toth, L.V. Pearce, R. Tran, Y. Wang, T. Szabo, and P.M. Blumberg Bioorg. Med. Chem. 12 2004 371 385
15. P.G. Andersson, H.E. Schink, and K. Osterlund J. Org. Chem. 63 1998 8067 8070
16. D.A. Klumpp, S.L. Aguirre, G.V. Sanches, and S.J. de Leon Org. Lett. 3 2001 2781 2784
17. D.A. Klumpp, G.V. Sanches, S.L. Aguirre, Y. Zhang, and S.J. de Leon J. Org. Chem. 67 2002 5028 5031
18. Y. Zhang, A. McElria, G.V. Sanches, D. Do, A. Gomez, S.L. Aguirre, R. Rendy, and D.A. Klumpp J. Org. Chem. 68 2003 5119 5122
19. K.Y. Koltunov, S. Walspurger, and J. Sommer Chem. Commun. 2004 1754 1755
20. K.Y. Koltunov, S. Walspurger, and J. Sommer Eur. J. Org. Chem. 2004 4039 4047
21. D.A. Klumpp, R. Rendy, Y. Zhang, A. Gomez, and A. McElria Org. Lett. 6 2004 1789 1792
22. R. Rendy, Y. Zhang, A. McElria, A. Gomez, and D.A. Klumpp J. Org. Chem. 69 2004 2340 2347
23. K.K.S. Sai, P.M. Esteves, E.T. da Penha, and D.A. Klumpp J. Org. Chem. 73 2008 6506 6512
24. F.D. King, and S. Caddick Org. Biomol. Chem. 10 2012 3244 3252
25. F.D. King, and S. Caddick Tetrahedron 69 2013 487 491
26. K.Y. Koltunov, G.K. Surya Prakash, G. Rasul, and G.A. Olah Heterocycles 62 2004 757 772
27. D.S. Ryabukhin, L.Y. Gurskaya, G.K. Fukin, and A.V. Vasilyev Tetrahedron 70 2014 6428 6443
28. A.V. Vasilyev Russ. Chem. Rev. 82 2013 187 204
29. T.-C. Wang, Y.-L. Chen, K.-H. Lee, and C.-C. Tzeng Synthesis 1997 87 90
30. M.C. Elliott, and S.V. Wordingham Synlett 2004 898 900
31. R.G. Parr, L.V. Szentpaly, and S. Liu J. Am. Chem. Soc. 121 1999 1922 1924
32. P.K. Chattaraj, S. Giri, and S. Duley Chem. Rev. 111 2011 PR43 PR75
33. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S. Iyengar, S. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C.G. Gonzalez, and J.A. Pople GAUSSIAN 03, Revision B.01 2003 Gaussian Pittsburgh, PA
34. L. Ackermann, A.V. Lygin, and N. Hofmann Org. Lett. 13 2011 3278 3281
35. M.K. Tay, E. About-Jaudet, N. Collignon, and P. Savignac Tetrahedron 45 1989 4415 4430
36. M.A. Weidner-Wells, S.A. Fraga-Spano, and I.J. Turchi J. Org. Chem. 63 1998 6319 6328
37. D.W. Adamson J. Chem. Soc. 1949 144 155