Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 19
1,221
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Piperidine Derivatives by Reduction of Pyridinium Salts

, &
Pages 3367-3379 | Received 26 Oct 2006, Published online: 05 Oct 2007

References

  • Pinder , A. R. 1992 . Azetidine, pyrrole, pyrrolidine, piperidine, and pyridine alkaloids . Nat. Prod. Rep. , 9 : 491 – 504 .
  • Dewick , P. M. 1997 . Medicinal Natural Products Chichester : John Wiley and Sons . Chapter 6
  • Michael , J. P. 2004 . Indolizidine and quinolizidine alkaloids . Nat. Prod. Rep. , 21 : 625 – 649 .
  • O'Hagan , D. 2002 . Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids . Nat. Prod. Rep. , 17 : 435 – 446 .
  • Maison , W. 2004 . Highlights in Bioorganic Chemistry Edited by: Schmuck , C. and Wennemers , H. 18 – 29 . New York : Wiley‐VCH .
  • Maier , C. A. and Wunsch , B. 2002 . Novel σ receptor ligands. Part 2. SAR of spiro[[2]benzopyran‐1,4′‐piperidines] and spiro[[2]benzofuran‐1,4′‐piperidines] with carbon substituents in position 3 . J. Med. Chem. , 45 : 4923 – 4930 .
  • Maier , C. A. and Wunsch , B. 2002 . Novel spiropiperidines as highly potent and subtype selective σ‐receptor ligands. Part 1 . J. Med. Chem. , 45 : 438 – 448 .
  • Zaveri , N. 2003 . Peptide and nonpeptide ligands for the nociceptin/orphanin FQ receptor ORL1: Research tools and potential therapeutic agents . Life Sci. , 73 : 663 – 678 .
  • Buffat , M. G. P. 2004 . Synthesis of piperidines . Tetrahedron , 60 : 1701 – 1729 .
  • Felpin , F. X. and Leberton , J. 2004 . Synthesis of 2,6‐dialkyl‐1,2,5,6‐tetrahydropyridines and their applications in total synthesis . Curr. Org. Synth. , 1 : 83 – 109 .
  • Weintraub , P. M. , Sabol , J. S. , Kane , J. M. and Borcherding , D. R. 2003 . Recent advances in the synthesis of piperidones and piperidines . Tetrahedron , 59 : 2953 – 2989 .
  • Laschat , S. and Dickner , T. 2000 . Stereoselective synthesis of piperidines . Synthesis , : 1781 – 1813 .
  • Rubiralata , M. , Giralt , E. and Diez , A. 1991 . Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidines and its Derivatives New York : Elsevier .
  • Zhou , X.‐F. , Lan , J. and Kwon , O. 2003 . An expedient phospohine‐catalyzed [4+2] annulation: Synthesis of highly functionalized tetrahydropyridines . J. Am. Chem. Soc. , 125 : 4716 – 4717 .
  • Wurz , R. P. and Fu , G. C. 2005 . Catalytic asymmetric synthesis of piperidine derivatives through the [4+2] annulation of imines with allenes . J. Am. Chem. Soc. , 127 : 12234 – 12235 .
  • Sakagami , H. , Kamikubo , T. and Ogasawara , K. 1996 . Novel reduction of 3‐hydroxypyridine and its use in the enantioselective synthesis of (+)‐pseudoconhydrine and (+)‐N‐methylpseudoconhydrine . Chem. Commun. , : 1433 – 1434 .
  • Sakagami , H. and Ogasawara , K. 2000 . Lipase‐mediated synthesis of enantiopure N‐carbobenzoxy‐3‐hydroxy‐1,2,3,4‐tetrahydro‐and N‐carbobenzoxy‐3‐hydroxy‐1,2,3,6‐tetrahydropyridines from 3‐hydroxypyridine . Synthesis , : 521 – 524 .
  • Tanaka , H. , Sakagami , H. and Ogasawara , K. 2002 . Diastereoselective synthesis of 3,5‐trans‐(+)‐(3R,5R)‐3‐carbomethoxycarbapenam from 3‐hydroxypyridine: questioning the stereochemical assignment of the natural product . Tetrahedron Lett. , 43 : 93 – 96 .
  • Cheng , C.‐Y. , Hsin , L.‐W. and Liou , J.‐P. 1996 . Novel radical synthesis of morphine fragments spiro[benzofuran‐3(2H),4′‐piperidine] and octahydro‐1H‐benzofuro[3,2‐e]isoquinoline . Tetrahedron , 52 : 10935 – 10944 .
  • Cheng , C.‐Y. , Liou , J.‐P. and Lee , M.‐J. 1997 . Synthesis of morphine fragments spiro[benzofuran‐3(2H),4′‐piperidine] and octahydro‐1H‐benzofuro[3,2‐e]isoquinoline by intramolecular Heck reaction . Tetrahedron Lett. , 38 : 4571 – 4574 .
  • Lambrecht , G. , Moser , U. , Mutscher , E. , Walther , G. and Wess , J. 1986 . Muscarinic ganglionic stimulants: conformationally restrained analoges related to [4‐[[N‐(3‐chlorophenyl)carbamoyl]oxy]‐2‐butynyl] trimethylammonium chloride . J. Med. Chem. , 29 : 1309 – 1311 .
  • Grierson , D. S. , Bettiol , J. L. , Buck , I. , Husson , H. P. , Rubiralta , M. and Diez , A. 1992 . Synthesis of 20‐deethylsilicine from a second‐generation 2‐cyano‐, DELTA, 3‐piperidine synthon . J. Org. Chem. , 57 : 6414 – 6421 .
  • Longlois , Y. , Longlois , N. and Potier , P. 1975 . Application d'un schema biogenetique en synthese totale: L'ellipticine . Tetrahedron Lett. , 16 : 955 – 958 .
  • Bosmans , J. R. M. A. , Love , C. J. , Decleyn , M. A. J. and D'haen , H. E. F. 1997 . Esters of 3‐hydroxy‐piperidinemethanol derivatives . PCT Int. Appl. , WO9730031 A1 79970821
  • Chang , M. , Chen , S. and Chang , N. 2002 . An efficient synthesis of N‐alkyl‐4‐substituted‐3H‐pyridine‐2,6‐dione. Synthesis of isoguvacine and MDL‐11,939 . Heterocycles , 57 : 2321 – 2334 .
  • Mitsunobu , O. 1981 . The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products . Synthesis , : 1 – 28 .
  • Charette , A. B. , Janes , M. K. and Boezio , A. A. 2001 . Mitsunobu reaction using triphenylphosphine linked to Non‐cross‐linked polystyrene . J. Org. Chem. , 66 : 2178 – 2180 .
  • Bitter , I. and Csokai , V. 2003 . An expedient route to p‐tert‐butylthiacalix[4]arene 1,3‐diethers via Mitsunobu reactions . Tetrahedron Lett. , 44 : 2261 – 2265 .
  • Person , D. E. , Wysong , R. D. and Breder , C. V. 1967 . Ortho bromination of phenols . J. Org. Chem. , 32 : 2358 – 2360 .
  • Marcot , B. , Mayrargue , J. , Moskowitz , H. , Ducrot , P. and Thal , C. 1995 . New stereoselective synthesis of spirocyclohexanbenzopyran derivatives . Heterocyclic Commun. , 1 : 289 – 296 .
  • Malan , P. L. and Dean , P. M. 1947 . The pyridylthioacetmorpholides and pyridylacetic acids . J. Am. Chem. Soc. , 69 : 1797 – 1798 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.