Abstract
Cyclocondensation of Schiff bases and substituted acetic acid with tosylimidazole afforded 2-azetidinones in good to excellent yields. This reaction works reliably well for monocyclic and spirocyclic 2-azetidinones. This reaction is green and efficient and the products can be purified by simple crystallisation.
References
1.
Soltani Rad M.N.
,
Behrouz S.
,
Faghihi M. A.
, and
Khalafi-Nezhad A.
, Tetrahedron Lett. , 2008 , 49 , 1115 .
2.
Byun H.-S.
,
Zhong N.
, and
Bittman R.
, Org. Synth. , 2004 , 10 , 690 .
3.
Mehta P.D.
,
Sengar N. P. S.
,
Pathak A. K.
, Eur. J. Med. Chem. , 2010 , 45 , 5541 .
4.
Alcaide B.
,
Almendros P.
, and
Aragoncillo C.
Chem. Rev. , 2007 , 107 , 4437 .
5.
Palomo C.
, and
Oiarbide M.
, Topics in heterocyclic chemistry , Springer-Verlag , Berlin , 2010 , Vol. 22 , pp. 211 –259 .
6.
Salunkhe D.S.
, and
Piste P. B.
, Int. J. Pharm. Sci. Rev. Res. , 2014 , 5 , 666 .
7.
Singh G. S.
Tetrahedron , 2003 , 59 , 7631 .
8.
Zarei M.
, and
Mohamadzadeh M.
, Tetrahedron , 2011 , 67 , 5832 .
9.
Keri R.S.
,
Hosamani K. M.
,
Shingalapur R. V.
, and
Reddy H. R. S.
, Eur. J. Med. Chem. , 2009 , 44 , 5123 .
10.
Zarei M.
, and
Maaqooli F.
, Synthetic Commun. , 2016 , 46 , 523 .
11.
Tidwell T.T.
, Ketenes II , John Wiley & Sons , New Jersey , 2006 , pp. 55 –192 .
12.
Jarrahpour A.
,
Motamedifar M.
,
Zarei M.
, and
Mimouni M.
, Phosphorus Sulfur Silicon , 2010 , 185 , 287 .
13.
Jarrahpour A.
,
Fadavi A.
, and
Zarei M.
, Bull. Chem. Soc. Jpn , 2011 , 84 , 320 .
14.
Zarei M.
, J. Chem. Res. , 2012 , 36 , 118 .
15.
Zarei M.
,
Karimi-Jaberi Z.
, and
Movahedi A.
, Synthetic Commun. , 2013 , 43 , 728 .
16.
Khademi Shiraz A.
, and
Zarei M.
, Monatsh. Chem. , 2015 , 146 , 941 .
17.
Zarei M.
, Monatsh. Chem. , 2013 , 144 , 1021 .
18.
Nahmany M.
, and
Melman A.
, J. Org. Chem. , 2006 , 71 , 5804 .
19.
Zarei M.
, J. Chem. Res. , 2013 , 37 , 25 .
20.
Zarei M.
, and
Jarrahpour A.
, Synlett , 2011 , 22 , 2572 .
21.
Zarei M.
, Tetrahedron , 2013 , 69 , 6620 .
22.
Wang Y.
,
Liang Y.
,
Jiao L.
,
Du D.-M.
, and
Xu J.
, J. Org. Chem. , 2006 , 71 , 6983 .
23.
Zarei M.
, Bull. Chem. Soc. Jpn , 2012 , 85 , 360 .
24.
Zarei M.
, and
Salehinezhad A.
, J. Chem. Res. , 2015 , 39 , 698 .