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2011 | 9 | 5 | 877-885
Tytuł artykułu

Intramolecular N to N acyl migration in conformationally mobile 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinoline] systems promoted by debenzylation conditions (HCOONH4/Pd/C)

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
We report an efficient and useful synthesis of new attractive spiropiperdine scaffolds 4 based on an intramolecular acyl transfer process in 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 3 using simple and mild debenzylation reaction conditions (HCOONH4/Pd/C). The compounds 3 were prepared by acylating 1-benzyl-4′-methyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 2 that are easily available from 1-benzyl-4-piperidone 1. The intramolecular character of this process was proven primarily through a crossover experiment technique. Through an examination of all spectroscopic information (1H, 13C NMR, VT-1H NMR, and 2D NMR) it was possible to correctly predict amide configurations and piperidine ring conformations of starting and final spiropiperidine compounds. [...]
Wydawca

Czasopismo
Rocznik
Tom
9
Numer
5
Strony
877-885
Opis fizyczny
Daty
wydano
2011-10-01
online
2011-07-24
Twórcy
  • Environmental Research Group, Environmental Chemistry Faculty, Santo Tomas University, A.A. 1076, Bucaramamga, Colombia
  • Laboratory of Organic & Biomolecular Chemistry, School of Chemistry, Industrial University of Santander, A.A. 678, Bucaramamga, Colombia, kouznet@uis.edu.co
Bibliografia
  • [1] A. Williams, K. T. Douglas, Chem. Rev. 75, 627(1975) http://dx.doi.org/10.1021/cr60297a006[Crossref]
  • [2] M.B. Smith, J. March, March’s Advanced Organic Chemistry, 5th edition (John Wiley & Sons, New York, 2001)
  • [3] A. Williams, Concerted Organic and Bio-organic Mechanisms (CRC Press, Boca Raton, 2000)
  • [4] P.E. Hanna, Adv. Pharmacol. 27, 401 (1994) http://dx.doi.org/10.1016/S1054-3589(08)61041-8[Crossref]
  • [5] M.W. Vetting, S.L.P. De Carvalho, M. Yu, S.S. Hegde, S. Magnet, S.L. Roderick, J.S. Blanchard, Arch. Biochem. Biophys. 433, 212 (2005) http://dx.doi.org/10.1016/j.abb.2004.09.003[Crossref]
  • [6] I. Kumar, R.F. Pratt, Biochemistry 9961 (2005) [Crossref]
  • [7] P.E. Hanna, Curr. Med. Chem. 3, 195 (1996)
  • [8] D. Kim, F.P. Guengerich, Annu. Rev. Pharmacol. Toxicol. 45, 27 (2005) http://dx.doi.org/10.1146/annurev.pharmtox.45.120403.100010[Crossref]
  • [9] L. Liu, A. Von Vett, N.K. Zhang, K.J. Walters, C.R. Wagner, P.E. Hanna, Chem. Res. Toxicol. 20, 1300 (2007) http://dx.doi.org/10.1021/tx7001614[Crossref]
  • [10] N.J. Butcher, J. Tiang, R.E. Minchin, Curr. Drug Metabolism 9, 498 (2008) http://dx.doi.org/10.2174/138920008784892128[Crossref]
  • [11] S. Ba-Saif, A.K. Luthra, A. Williams, J. Am. Chem. Soc. 109, 6362 (1987) http://dx.doi.org/10.1021/ja00255a021[Crossref]
  • [12] S. Ba-Saif, A.K. Luthra, A. Williams, J. Am. Chem. Soc. 111, 2647 (1989) http://dx.doi.org/10.1021/ja00189a045[Crossref]
  • [13] A.C. Hengge, R.A. Hess, J. Am. Chem. Soc. 116, 11256 (1994) http://dx.doi.org/10.1021/ja00104a007[Crossref]
  • [14] E. Chrystiuk, A. Williams, J. Am. Chem. Soc. 109, 3040 (1987) http://dx.doi.org/10.1021/ja00244a028[Crossref]
  • [15] M. Skwarczynsk, Y. Kiso, Curr. Med. Chem. 26, 2813 (2007) http://dx.doi.org/10.2174/092986707782360123[Crossref]
  • [16] A. Volonterio, C. Ramirez de Arellano, M. Zanda, J. Org. Chem. 70, 2161 (2005) http://dx.doi.org/10.1021/jo0480848[Crossref]
  • [17] A. Volonterio, M. Zanda, J. Org. Chem. 73, 7486 (2008) http://dx.doi.org/10.1021/jo801288s[Crossref]
  • [18] P.M. Weintraub, J.S. Sabol, J.M. Kane, D.R. Borcherding, Tetrahedron 59, 2953 (2003) http://dx.doi.org/10.1016/S0040-4020(03)00295-3[Crossref]
  • [19] P.S. Watson, B. Jiang, B. Scott, Org. Lett. 2, 3679 (2000) http://dx.doi.org/10.1021/ol006589o[Crossref]
  • [20] G. Brieger, T.J. Nestrick, Chem. Rev. 74, 567 (1974) http://dx.doi.org/10.1021/cr60291a003[Crossref]
  • [21] S. Bartane, I. Schoen, P.M. Pellioniszne, B. Kiss, E. Karpati, A. Kis-Varga, E. Lapis, A. Gere, I. Laszlovszky, S. Farkas, K. Csomov, C. Horvath, S. Szabo, P. Horvath, J. Laszy, C. Szantay, Hung. Teljes HU 76, 345, 1997; Chem. Abstr. 128, 154093f (1998) (In Hungarian)
  • [22] L.Y. Vargas Méndez, V.V. Kouznetsov, Tetrahedron Lett. 48, 2509 (2007) http://dx.doi.org/10.1016/j.tetlet.2007.02.037[Crossref]
  • [23] V.V. Kouznetsov, P.B. Díaz, M.C.M. Sanabria, L.Y. Vargas Méndez, J.C. Poveda, E.E. Stashenko, A. Bahsas, J. Amaro-Luis, Lett. Org. Chem. 2, 29 (2005) http://dx.doi.org/10.2174/1570178053400234[Crossref]
  • [24] L.A. La Planche, M.T. Rogers, J. Am. Chem. Soc. 85, 3728 (1963) http://dx.doi.org/10.1021/ja00906a002[Crossref]
  • [25] W.E. Stewart, T.H. Siddall, Chem. Rev. 70, 517 (1970) http://dx.doi.org/10.1021/cr60267a001[Crossref]
  • [26] R.A. Johnson, J. Org. Chem. 33, 3627 (1968) http://dx.doi.org/10.1021/jo01273a060[Crossref]
  • [27] M.J. Frisch et al., Gaussian 03, Revision D.1 (Gaussian Inc., Pittsburgh, 1995)
  • [28] L.M. Jackman, Dynamic nuclear magnetic resonance spectroscopy (Academic Press, New York, 1975) cap. 7
  • [29] M. Oki, Aplications of dynamic NMR spectroscopy to organic chemistry (VCH Publishers, Inc, Deerfield Beach, Florida, 1985)
  • [30] H. Paulsen, K. Todt, Angew. Chem. Int. Ed. Engl. 5, 899 (1966) http://dx.doi.org/10.1002/anie.196608992[Crossref]
  • [31] J.B. Lambert, R.G. Keske, R.E. Carhart, A.P. Jovanovich, J. Am. Chem. Soc. 89, 3761 (1967) http://dx.doi.org/10.1021/ja00991a014[Crossref]
  • [32] D.M. Lynch, W.J. Cole, J. Org. Chem. 31, 3337 (1966) http://dx.doi.org/10.1021/jo01348a052[Crossref]
  • [33] F. A. Carroll, Perspectives on structure and mechanism in organic chemistry (Brooks/Cole Publishing Company, Pacific Grove, California, 1998)
  • [34] M.B. Smith, J. March, March’s advanced organic chemistry: reactions, mechanisms, and structure (John Wiley & Sons, Inc., New York, 2001)
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-011-0082-y
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