Abstract
An efficient synthesis of 1,3-thiazolidine derivatives has been achieved in which 2-pyridinecarboxaldehyde oxime was employed as a base catalyst to effect cyclisation between aziridines and CS2 in DMF at 40 °C. A similar reaction between aziridines and thiocyanates yielded 1,3-thiazoline-2-imine derivatives
References
1.
Wu J.
,
Hou X.
, and
Dai L.
, J. Org. Chem. , 2000 , 65 , 1344 .
2.
Loncanic C.
, and
Wulff W. D.
, Org. Lett. , 2001 , 3 , 3675 .
3.
Li Z.
,
Fernandez M.
, and
Jacobsen E. N.
, Org. Lett. , 1999 , 1 , 1611 .
4.
Righi G.
,
D'Achille R.
, and
Bonini C.
, Tetrahedron Lett. , 1996 , 37 , 6893 .
5.
Davis F.A.
,
Reddy G. V.
, and
Liang C. H.
, Tetrahedron Lett. , 1997 , 38 , 5139 .
6.
Almena J.
,
Foubelo F.
, and
Yus M.
, J. Org. Chem. , 1994 , 59 , 3210 .
7.
Lindström U.M.
, and
Somfai P.
, J. Am. Chem. Soc. , 1997 , 119 , 8385 .
8.
Vogel C.
, Synthesis , 1997 , 497 .
9.
Hedley S.J.
,
Moran W. J.
,
Prenzel A. H. G. P.
,
Price D. A.
, and
Harrity J. P. A.
, Synlett. , 2001 , 1596 .
10.
Dubois L.
,
Mehta A.
,
Tourette E.
, and
Dodd R. H.
, J. Org. Chem. , 1994 , 59 , 434 .
11.
Dauban P.
,
Dubois L.
,
Dau M. E. T. H.
, and
Dodd R. H.
, J. Org. Chem. , 1995 , 60 , 2035 .
12.
Medina E.
,
Moyano A.
,
Pericàs M. A.
, and
Riera A.
, J. Org. Chem. , 1998 , 63 , 8574 .
13.
Ferraris D.
,
Drury W. J.
,
Cox C.
, and
Lectka T.
, J. Org. Chem. , 1998 , 63 , 4568 .
14.
Wu J.Y.
,
Luo Z. B.
,
Dai L. X.
, and
Hou X. L.
, J. Org. Chem. , 2008 , 73 , 9137 .
15.
Ghazanfarpour-Darjani M.
, and
Khodakarami A.
, Monatsh Chem. , 2016 , 147 , 829 .
16.
Yavari I.
, and
Ghazanfarpour-Darjani M.
, J. Sulphur Chem. , 2014 , 35 , 477 .
17.
Tanner D.
, Angew. Chem. Int. Ed. Engl. , 1994 , 33 , 599 .
18.
Stamm H.
, J. Prakt. Chem. , 1999 , 341 , 319 .
19.
Hu X.E.
, Tetrahedron , 2004 , 60 , 2701 .
20.
Ando T.
,
Kano D.
,
Minakata S.
,
Ryu N.
, and
Komatsu M.
, Tetrahedron , 1998 , 54 , 13485 .