Abstract
A green method for the synthesis of thiazolo[3,2-α]pyridine derivatives via the coupling of malononitrile, an aryl aldehyde and methyl thioglycolate in an ionic liquid has been developed. The advantages of this protocol are that it is non-toxic, no by-products are formed, short reaction times are required and high yields are obtained. Thiazolo [3,2-α]pyridines have important biological and medical applications.
References
1.
Mullan M.J.
,
Paris D.
, and
Bakshi P.
, WO 2008070875, 2008, Chem. Abstr. , 2008 , 149 , 45259 .
2.
Vadivelan S.
,
Sinha B.N.
,
Irudayam S.J.
, and
Jagarlapudi S.A.R.P.
, J. Chem. Inf. Model. , 2007 , 47 , 1526 .
3.
Park H.
,
Hwang K.Y.
,
Oh K.H.
,
Kim Y.H.
,
Lee J.Y.
, and
Kim K.
, Bioorg. Med. Chem. , 2008 , 16 , 284 .
4.
Manhi F.M.
, and
Soliman G.A.
, Chem. Abstr. , 1993 , 121 , 50029 .
5.
El-Hag Ali G.
,
Khalil A.
,
Lamphon R.
, and
El-Maghraby A.
, Phosphorus, Sulfur Silicon Relat. Elem. , 2005 , 180 , 1909 .
6.
El-Maghraby A.A.
,
El-Hag Ali G.A.M.
,
Ahmed A.H.A.
, and
El-Gaby M.S.A.
, Phosphorus, Sulfur Silicon Relat. Elem. , 2002 , 177 , 293 .
7.
Shi F.
,
Li C.M.
,
Xia M.
,
Miao K.J.
,
Zhao Y.X.
,
Tu S.J.
,
Zheng W.F.
,
Zhang G.
, and
Ma N.
Bioorg. Med. Chem. , 2009 , 19 , 5565 .
8.
Abdel-latif F.F.
,
Mohammed Y.S.
,
Abdel-ghani H.
,
Ahmed E. Kh.
, and
El-gawish E.H.
, Phosphorus, Sulfur, Silicon , 1993 , 78 , 251 .
9.
He L.
,
Tao G.H.
,
Liu W.S.
,
Xiong
,
Xiong W.
,
Wang T.
, and
Kou Y.
, Chin. Chem. Lett. , 2006 , 17 , 321 .
10.
Fischer T.
,
Sethi A.
,
Welton T.
, and
Woolf J.
Tetrahedron Lett. , 1999 , 40 , 793 .
11.
Hagiwara H.
,
Shimizu Y.
,
Hoshi T.
,
Suzuki T.
,
Ando M.
,
Ohkubo K.
, and
Yokoyama C.
, Tetrahedron Lett. , 2001 , 42 , 4349 .
12.
Potdar M.K.
,
Mohile S.S.
, and
Salunkhe M.M.
, Tetrahedron Lett. , 2001 , 42 , 9285 .
13.
Peng J.
, and
Deng Y.
, Tetrahedron Lett. , 2001 , 42 , 5917 .
14.
Xu X. X.
,
Wei Z.L.
, and
Bo X.
, Chin. J. Org. Chem. , 2006 , 3 , 354 .
15.
Wang B.
,
Gu Y.
,
Luo C.
,
Yang T.
,
Yang L.
, and
Suo J.
, Tetrahedron Lett. , 2004 , 45 , 3417 .
16.
Yuan X.L.
,
Zhang S.J.
, and
Lu X.M.
, J. Chem. Eng. Data , 2007 , 52 , 596 .
17.
Al-Matar H.M.
,
Khalil K.D.
,
Meier H.
,
Kolshorn H.
, and
Elnagdi M. H.
, Arkivoc , 2008 , 288 .
18.
El-Maghraby A.A.
,
Gameel A.M.
,
Ali E.H.
,
Ahmed A.H.A.
, and
El-Gaby M.S.A.
, Phosphorus, Sulfur Silicon , 2002 , 177 , 293 .
19.
Abdel-latif F.F.
,
Mohammed Y.S.
,
Abdel-ghani H.
,
Ahmed E. Kh.
, and
El-gawish E.H.
Phosphorus, Sulfur, Silicon , 1993 , 78 , 251 .
20.
Elnagdi M.H.
,
Elmoghayar M.R.H.
,
Elghandour A.H.H.
, and
Sadek K. U.
, Egypt. Sulfur Lett. , 1989 , 9 , 109 .
21.
Elnagdi M.H.
,
Elmoghayar M.R.H.
,
Elghandour A.H.H.
, and
Sadek K.U.
, Coll. Czech. Chem. Commun. , 1990 , 55 , 745 .