Abstract
The novel one-pot four-component reactions of 2-aminothiazole, aldehydes, Meldrum's acid and aliphatic alcohols were investigated, and a series of unexpected compounds, 3-(2-aminothiazol-5-yl)-3-arylpropanoates, were synthesised under catalyst-free conditions. The protocol has advantages of mild conditions, high yield and simple work-up procedure. Thiazoles are important in the field of organic and medicinal chemistry.
Keywords
References
1.
Fink B.A.
,
Mortensen D.S.
,
Stauffer S.R.
,
Aron Z.D.
, and
Katzenellenbogen J.A.
, Chem. Biol. , 1999 , 6 , 205 .
2.
Muijlwijk-Koezen J.E.
,
Timmerman H.
,
Vollinga R.C.
,
Drabbe-Kunzel J.F.
,
Groote M.
,
Visser S.
, and
Ijzerman A. P.
, J. Med. Chem. , 2001 , 44 , 749 .
3.
Panico A.M.
,
Geronikaki A.
,
Mgonzo R.
,
Cardile V.
,
Gentile B.
, and
Doytchinova I.
, Bioorg. Med. Chem. , 2003 , 11 , 2983 .
4.
Mokale S.N.
,
Sanap P.T.
, and
Shinde D.B.
, Eur. J. Med. Chem. , 2010 , 45 , 3096 .
5.
Mokale S.N.
,
Elgire R.D.
,
Sakle N.
, and
Shinde D.B.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 682 .
6.
Alexandru M.G.
,
Velickovic T.C.
,
Jitaru I.
,
Grguric-Sipka S.
, and
Draghici C.
, Central Eur. J. Chem. , 2010 , 8 , 639 .
7.
Zhou X.
,
Shao L.
,
Jin Z.
,
Liu J.B.
,
Dai H.
, and
Fang J.X.
, Heteroatom Chem. , 2007 , 18 , 55 .
8.
Wender P.A.
,
Handy S.T.
, and
Wright D.L.
, Chem. Ind. , 1997 , 765 .
9.
Trost B.M.
, Angew. Chem., Int. Ed. Engl. , 1995 , 34 , 259 .
10.
Weber L.
,
Illgen K.
, and
Almstetter M.
, Synlett , 1999 , 366 .
11.
Bienayme H.
,
Hulme C.
,
Oddon G.
, and
Schmitt P.
, Chem. Eur. J. , 2000 , 6 , 3321 .
12.
Li Z.
,
Ma Y.H.
,
Xu J.
,
Shi J.H.
, and
Cai H.F.
, Tetrahedron Lett. , 2010 , 51 , 3922 .
13.
Li Z.
,
Tian G.Q.
, and
Ma Y.H.
, Synlett , 2010 , 2164 .
14.
Zhao Z.X.
, and
Li Z.
, J. Braz. Chem. Soc. , 2011 , 22 , 148 .
15.
Li Z.
,
Ma X.L.
,
Liu J.
,
Feng X.
,
Tian G.Q.
, and
Zhu A.G.
, J. Mol. Catal. A: Chem. , 2007 , 272 , 132 .
16.
Li Z.
,
Li Y.B.
,
Cai H.F.
,
Xu J.
, and
Shi J.H.
, Lett. Org. Chem. , 2010 , 7 , 467 .
17.
Pouchert C.J.
, and
Behnke J.
Aldrich library of 13C and 1H FT-NMR spectra. Aldrich Chemical Company , 1993 .