Abstract
A simple and convenient synthesis of 2-azetidinone derivatives from the reaction of a pre-mixture of amines and aldehydes with carboxylic acids in the presence of diethyl chlorophosphate by [2+2] cycloaddition reaction is described. Separation and purification of imines as intermediates were not required. The methodology is convenient and good to excellent yields of products were obtained with simple purification.
References
1.
Long T.E.
, and
Turos E.
, Curr. Med. Chem. Anti-Infect. Agents , 2002 , 1 , 251 .
2.
Hwu J.R.
,
Ethiraj S.K.
, and
Hakimelahi G.H.
, Mini-Rev. Med. Chem. , 2003 , 3 , 305 .
3.
Xu X.
,
Fu R.
,
Chen J.
,
Chen S.
, and
Bai S.
, Bioorg. Med. Chem. Lett. , 2007 , 17 , 101 .
4.
Mehta P.D.
,
Sengar N.P.S.
, and
Pathak A.K.
, Eur. J. Med. Chem. , 2010 , 45 , 5541 .
5.
Veinberg G.
,
Vorona M.
,
Shestakova I.
,
Kanepe I.
, and
Lukevics E.
, Curr. Med. Chem. , 2003 , 10 , 1741 .
6.
Alcaide B.
, and
Almendros P.
, Curr. Med. Chem. , 2004 , 11 , 1921 .
7.
Ojima I.
, and
Delaloge F.
, Chem. Soc. Rev. , 1997 , 26 , 377 .
8.
Palomo C.
, and
Oiarbide M.
, Topics in heterocyclic chemistry , ed.
Banik B.K.
, Springer-Verlag ; Berlin , 2010 ; Vol. 22 , p. 211 .
9.
Suffness M.
, Taxol science and applications , CRC Press , Boca Raton, Florida , 1995 .
10.
Alcaide B.
, and
Almendros P.
, Progress in heterocyclic chemistry , 2011 , 22 , 85 .
11.
Georg G.I.
, The organic chemistry of β-lactams , Verlag Chemie , New York , 1993 .
12.
Staudinger H.
, Liebigs Ann. Chem. , 1907 , 356 , 51 .
13.
Wang Z.
, Comprehensive organic name reactions and reagents , John Wiley & Sons , 2010 , p. 2636 .
14.
Xu J.
, Arkivoc 2009 , (ix), 21 .
15.
Fodor L.
,
Csomos P.
,
Holczbauer T.
,
Kalman A.
,
Csampai A.
, and
Sohar P.
, Tetrahedron Lett. , 2011 , 52 , 224 .
16.
Janikowska K.
,
Pawelska N.
, and
Makowiec S.
, Synthesis , 2011 , 69 .
17.
Dubey A.
,
Srivastava S.K.
, and
Srivastava S.D.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 569 .
18.
Keri R.S.
,
Hosamani K.M.
,
Shingalapur R.V.
, and
Reddy H.R.S.
, Eur. J. Med. Chem. , 2009 , 44 , 5123 .
19.
Keri R.S.
, and
Hosamani K.M.
, Monatsh. Chem. , 2010 , 141 , 883 .
20.
Jarrahpour A.
,
Motamedifar M.
,
Zarei M.
, and
Mimouni M.
, Phosphorus Sulfur Silicon , 2010 , 185 , 287 .
21.
Jarrahpour A.
, and
Zarei M.
, Molecules , 2006 , 11 , 49 .
22.
Jarrahpour A.
, and
Ebrahimi E.
, Molecules , 2010 , 15 , 515 .
23.
Seetharamareddy H.R.
,
Hosamani K.M.
, and
Keri R.S.
, Synth. Commun. , 2010 , 40 , 450 .
24.
Jarrahpour A.
,
Ebrahimi E.
,
De Clercq E.
,
Sinou V.
,
Latour C.
,
Bouktab L.D.
, and
Brunel J.M.
, Tetrahedron , 2011 , 67 , 8699 .
25.
Banik B.K.
,
Banik I.
, and
Becker F.F.
, Eur. J. Med. Chem. , 2010 , 45 , 846 .
26.
Jarrahpour A.
, and
Zarei M.
, Tetrahedron Lett. , 2009 , 50 , 1568 .
27.
Jarrahpour A.
, and
Zarei M.
, Tetrahedron , 2009 , 65 , 2927 .
28.
Bose A.K.
,
Manhas M.S.
,
Amin S.G.
,
Kapur J.C.
,
Kreder J.
,
Mukkavilli L.
,
Ram B.
, and
Vincent J.E.
, Tetrahedron Lett. , 1979 , 20 , 2771 .
29.
Bernardi L.
,
Bonini B.F.
,
Comes-Franchini M.
,
Dessole G.
,
Fochi M.
, and
Ricci A.
, Eur. J. Org. Chem. , 2005 , 3326 .
30.
Jarrahpour A.
, and
Zarei M.
, Molecules , 2007 , 12 , 2364 .
31.
Matsui S.
,
Hashimoto Y.
, and
Saigo K.
, Synthesis , 1998 , 1161 .
32.
Jarrahpour A.
, and
Zarei M.
, Tetrahedron Lett. , 2007 , 48 , 8712 .
33.
Isobe T.
, J. Org. Chem. , 1999 , 64 , 6989 .
34.
Meshram J.
,
Ali P.
, and
Tiwari V.
, J. Het. Chem. , 2010 , 47 , 1454 .
35.
Jarrahpour A.
,
Fadavi A.
, and
Zarei M.
, Bull. Chem. Soc. Jpn. , 2011 , 84 , 320 .
36.
Palomo C.
,
Aizpurua J.M.
,
Urchegui R.
,
Iturburu M.
,
de Retana A.O.
, and
Cuevas C.
, J. Org. Chem. , 1991 , 56 , 2244 .
37.
Zarei M.
, and
Mohamadzadeh M.
, Tetrahedron , 2011 , 67 , 5832 .
38.
Nahmany M.
, and
Melman A.
, J. Org. Chem. , 2006 , 71 , 5804 .
39.
Jarrahpour A.
, and
Zarei M.
, Synlett , 2011 , 2572 .
40.
Jarrahpour A.
, and
Zarei M.
, Tetrahedron , 2010 , 66 , 5017 .
