Abstract
1-Methyl-2-oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO4]) is used as an ionic liquid catalyst for the one-pot three-component synthesis of highly substituted piperidines from aromatic aldehydes, anilines and β–ketoesters in refluxing ethanol. This homogeneous catalyst procedure has the advantages of easy work-up, no need for column chromatography, simple and readily available precursors, and good to high yields.
References
1.Special issue on ionic liquids , Acc. Chem. Res. , 2007 , 40 , 1077 .
2.
Wasserscheid P.
, and
Welton T.
, Ionic liquids in synthesis , Wiley-VCH , 2008 .
3.
Park J.
, and
Chae J.
, Synlett , 2010 , 1651 .
4.
Misra M.
,
Pandey S.K.
,
Pandey V.P.
,
Pandey J.
,
Tripathi R.
, and
Tripathi R.P.
, Bioorg. Med. Chem. , 2009 , 17 , 625 .
5.
Petit S.
,
Nallet J.P.
,
Guillard M.
,
Dreux J.
,
Chermat R.
,
Poncelet M.
,
Bulach C.
,
Simon P.
,
Fontaine C.
,
Barthelmebs M.
, and
Imbs J.L.
, Eur. J. Med. Chem. , 1991 , 26 , 19 .
6.
Zhou Y.
,
Gregor V.E.
,
Ayida B.K.
,
Winters G.C.
,
Sun Z.
,
Murphy D.
,
Haley G.
,
Bailey D.
,
Froelich J.M.
,
Fish S.
,
Webber S.E.
,
Hermann T.
, and
Wall D.
, Bioorg. Med. Chem. Lett. , 2007 , 17 , 1206 .
7.
Borza I.
, and
Domany G.
, Curr. Top. Med. Chem. , 2006 , 6 , 687 .
8.
Mony L.
,
Kew J.N.
,
Gunthorpe M.J.
, and
Paoletti P.
, Br. J. Pharmacol. , 2009 , 157 , 1301 .
9.
Bin H.
,
Crider A.M.
, and
Stables J.P.
, Eur. J. Med. Chem. , 2001 , 36 , 265 .
10.
Gitto R.
,
De Luca L.
,
Ferro S.
,
Occhiuto F.
,
Samperi S.
,
De Sarro G.
,
Russo E.
,
Ciranna L.
,
Costa L.
, and
Chimirri A.
, ChemMedChem , 2008 , 3 , 1539 .
11.
Beeler A.B.
,
Gadepalli R.S.V.S.
,
Steyn S.
,
Castagnoli N.
Jr.
, and
Rimoldi J.M.
, Bioorg. Med. Chem. , 2003 , 11 , 5229 .
12.
Deskus J.A.
,
Epperson J.R.
,
Charles P.S.
,
Joseph A.C.
,
Dextraze P.
,
Qian-Cutrone J.
,
Gao Q.
,
Ma B.
,
Beno B.R.
,
Mattson G.K.
,
Molski T.F.
,
Krause R.G.
,
Taber M.T.
,
Lodge N.J.
, and
Mattson R.J.
, Bioorg. Med. Chem. Lett. , 2007 , 17 , 3099 .
13.
Gwaltney S.L.
II
,
O'Connor S.J.
,
Nelson L.T.J.
,
Sullivan G.M.
,
Imade H.
,
Wang W.
,
Hasvold L.
,
Li Q.
,
Cohen J.
,
Gu W.-Z.
,
Tahir S.K.
,
Bauch J.
,
Marsh K.
,
Ng S.-C.
,
Frost D.J.
,
Zhang H.
,
Muchmore S.
,
Jakob C.G.
,
Stoll V.
, and
Hutchins C.
, Bioorg. Med. Chem. Lett. , 2003 , 13 , 1359 .
14.
Nara S.
,
Tanaka R.
,
Eishima J.
,
Hara M.
,
Takahashi Y.
,
Otaki S.
,
Foglesong R.J.
,
Hughes P.F.
,
Turkington S.
, and
Kanda Y.
, J. Med. Chem. , 2003 , 46 , 2467 .
15.
Van Voorhis W.C.
,
Rivas K.L.
,
Bendale P.
,
Nallan L.
,
Hornéy C.
,
Barrett L.K.
,
Bauer K.D.
,
Smart B.P.
,
Ankala S.
,
Hucke O.
,
Verlinde C.L.M.J.
,
Chakrabarti D.
,
Strickland C.
,
Yokoyama K.
,
Buckner F.S.
,
Hamilton A.D.
,
Williams D.K.
,
Lombardo L.J.
,
Floyd D.
, and
Gelb M.H.
, J. Med. Chem. , 2005 , 48 , 3704 .
16.
Von Itzstein M.
,
Wu W.-Y.
,
Kok G.B.
,
Pegg M.S.
,
Dyason J.C.
,
Jin B.
,
Phan T.V.
,
Smythe M.L.
,
White H.F.
,
Oliver S.W.
,
Colman P.M.
,
Varghese J.N.
,
Ryan D.M.
,
Woods J.M.
,
Bethell R.C.
,
Hothman V.J.
,
Camreon J.M.
, and
Penn C.R.
, Nature , 1993 , 363 , 418 .
17.
Kim C.U.
,
Lew W.
,
Williams M.A.
,
Liu H.
,
Zhang L.
,
Swaminathan S.
,
Bischofberger N.
,
Chen M.S.
,
Mendel D.B.
,
Tai C.Y.
,
Laver W.G.
, and
Stevens R.C.
, J. Am. Chem. Soc. , 1997 , 119 , 681 .
18.
Chand P.
,
Kotian P.L.
,
Dehghani A.
,
El-Kattan Y.
,
Lin T.-H.
,
Hutchison T.L.
,
Babu Y.S.
,
Bantia S.
,
Elliott A.J.
, and
Montgomery J.A.
, J. Med. Chem. , 2001 , 44 , 4379 .
19.
Goss P.E.
,
Baker M.A.
,
Carver J.P.
, and
Dennis J.W.
, Clin. Cancer Res. , 1995 , 1 , 935 .
20.
Nishimura Y.
,
Satoh T.
,
Adachi H.
,
Kondo S.
,
Takeuchi T.
,
Azetaka M.
,
Fukuyasu H.
, and
Iizuka Y.
, J. Med. Chem. , 1997 , 40 , 2626 .
21.
Zitzmann N.
,
Mehta A.S.
,
Carrouee S.
,
Butters T.D.
,
Platt F.M.
,
McCauley J.
,
Blumberg B.S.
,
Dwek R.A.
, and
Block T.M.
, Proc. Natl. Acad. Sci. USA , 1999 , 96 , 11878 .
22.
Karlsson G.B.
,
Butters T.D.
,
Dwek R.A.
, and
Platt F.M.
, J. Biol. Chem. , 1993 , 268 , 570 .
23.
Groopman J.E.
, Rev. Infect. Dis. , 1990 , 12 , 931 .
24.
Treadway J.L.
,
Mendys P.
, and
Hoover D.J.
, Expert Opin. Invest. Drugs , 2001 , 10 , 439 .
25.
Jacob G.S.
, Curr. Opin. Struct. Biol. , 1995 , 5 , 605 .
26.
Clarke P.A.
,
Zaytzev A.V.
, and
Whitwood A.C.
, Tetrahedron Lett. , 2007 , 48 , 5209 .
27.
Clarke P.A.
,
Zaytzev A.V.
, and
Whitwood A.C.
, Synthesis , 2008 , 3530 .
28.
Khan A.T.
,
Parvin T.
, and
Choudhury L.H.
, J. Org. Chem. , 2008 , 73 , 8398 .
29.
Khan A.T.
,
Lal M.
, and
Khan M.M.
, Tetrahedron Lett. , 2010 , 51 , 4419 .
30.
Khan A.T.
,
Khan M.M.
,
Bannuru K.K.R.
, Tetrahedron , 2010 , 66 , 7762 .
31.
Wang H.-J.
,
Mo L.-P.
, and
Zhang Z.-H.
, ACS Comb. Sci. , 2011 , 13 , 181 .
32.
Mishra S.
, and
Ghosh R.
, Tetrahedron Lett. , 2011 , 52 , 2857 .
33.
Ramachandran R.
,
Jayanthi S.
, and
Jeong Y.T.
, Tetrahedron , 2012 , 68 , 363 .
34.
Mukhopadhyay C.
,
Rana S.
,
Butcher R.J.
, and
Schmiedekamp A.M.
, Tetrehedron Lett. , 2011 , 52 , 5835 .
35.
Brahamachari G.
, and
Das S.
, Tetrahedron Lett. , 2012 , 53 , 1479 .
36.
Khandan-Barani K.
,
Maghsoodlou M.T.
,
Habibi-Khorassani S.M.
,
Hazeri N.
, and
Sajadikhah S.S.
, J. Chem. Res. 2011 , 35 , 231 .
37.
Maghsoodlou M.T.
,
Habibi-Khorasani S.M.
,
Heydari R.
,
Hazeri N.
,
Sajadikhah S.S.
,
Rostamisadeh M.
, and
Keishams L.
, Turk. J. Chem. , 2010 , 34 , 565 .
38.
Hazeri N.
,
Habibi-Khorassani S.M.
,
Maghsoodlou M.T.
,
Marandi G.
,
Nassiri M.
, and
Shahzadeh A.G.
, J. Chem. Res. , 2006 , 215 .
39.
Maghsoodlou M.T.
,
Hazeri N.
,
Habibi-Khorassani S.M.
,
Solimani V.
,
Marandi G.
, and
Razmjoo Z.
, J. Chem. Res. , 2008 , 198 .
40.
Sajadikhah S.S.
,
Maghsoodlou M.T.
,
Hazeri N.
,
Habibi-Khorassani S.M.
, and
Shams-Najafi S.J.
, Monatsh. Chem. 2012 , 143 , 939 .
41.
Lashkari M.
,
Maghsoodlou M.T.
,
Hazeri N.
,
Habibi-Khorassani S.M.
,
Sajadikhah S.S.
, and
Doostmohamadi R.
, Synth. Commun. DOI: 10.1080/00397 911.2011.601534.
42.
Xie C.
,
Li H.
,
Li L.
,
Yu S.
, and
Liu F.
, J. Hazar. Mater. 2008 , 151 , 847 .
