Abstract
A series of novel spiropyrrolidine derivatives were synthesised via three-component 1,3-dipolar cycloaddition reactions of 1-(1-methylpyrrole-2-yl)-3-aryl-2-cyano-1-propenones, isatin and sarcosine in refluxing methanol. The method affords a fast one-pot synthesis of spiroheterocycles in high yields. Their structures were established by 1H NMR, IR and elementary analysis.
Keywords
References
1.
Tsuge O.
, and
Kanemasa S.
, Advances in heterocyclic chemistry , Vol. 45 , ed.
Katritzky A.R.
, Academic Press , San Diego , 1989 , p. 231 .
2.
Grigg R.
, and
Sridharan V.
, Advances in cycloaddition , Vol.3 , ed.
Curran D.P.
, Jai Press , London , 1993 , p 161 .
3.
Pandey G.
,
Banerjee P.
, and
Gadre S.R.
, Chem. Rev. , 2006 , 106 , 4484 .
4.
Rehn S.
,
Bergman J.
, and
Stensland B.
, Eur. J. Org. Chem. , 2004 , 413 .
5.
Sebahar P.R.
,
Osafa H.
,
Usui T.
, and
Williams R.M.
, Tetrahedron , 2002 , 58 , 6311 .
6.
Lukoyanova O.
,
Cardona C.M.
,
Altable M.
,
Filippone S.
,
Domenech A.M.
,
Martin N.
, and
Echegoyen L.
, Angew. Chem. , 2006 , 118 , 7590 .
7.
Chande M.S.
,
Verma R.S.
, and
Barve P.A.
, Eur. J. Med. Chem. , 2005 , 40 , 1143 .
8.
Sriram D.
,
Yogeeswari P.
, and
Madhu K.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 876 .
9.
Abou-Gharbia M.A.
, and
Doukas P.H.
, Heterocycles , 1979 , 12 , 637 .
10.
Kornet M.J.
, and
Thio A.P.
, J. Med. Chem. , 1976 , 19 , 892 .
11.
Marti C.
, and
Carreira E.
, Eur. J. Org. Chem. , 2003 , 2209 .
12.
Lakshmi N.V.
,
Thirumurugan P.
, and
Peruml P.
, Tetrahedron Lett. , 2010 , 51 , 1064 .
13.
Geng L.J.
,
Feng G.L.
, and
Yu J.G.
, J. Chem. Res. , 2010 , 34 , 333 .
14.
Geng L.J.
,
Feng G.L.
, and
Yu J.G.
, J. Chem. Res. , 2010 , 34 , 565 .