Abstract
An efficient synthesis of thiopyran derivatives via one-pot reactions between methyl propiolates, aryl isothiocyanates and acetylacetone in water is described.
References
1.
Anastas
P.
, and
Williamson
T.
, Green chemistry, frontiers in benign chemical synthesis and procedures. Oxford Science Publications , New York , 1998 .
2.
Cave
G.W.V.
,
Raston
C.L.
, and
Scott
J.L.
, Chem. Commun. , 2001 , 21 , 2159 .
3.
Sheldon
R.A.
, Chem. Ind. (London) , 1997 , 12 .
4.
Breslow
R.
, Acc. Chem. Res. , 1991 , 24 , 159 .
5.
Li
C.J.
, and
Chang
T.H.
, Organic reactions in aqueous media. Wiley , New York , 1997 , p. 795 .
6.
Lindström
U.M.
, Chem. Rev. , 2002 , 102 , 2751 .
7.
Shu
K.
, and
Kei
M.
, Acc. Chem. Res. , 2002 , 35 , 209 .
8.
Li
C.J.
, Chem. Rev. , 2005 , 105 , 3095 .
9.
Narayan
S.
,
Muldoon
J.
,
Finn
M.G.
,
Fokin
V.V.
,
Kolb
H.C.
, and
Sharpless
K.B.
, Angew. Chem., Int. Ed. , 2005 , 44 , 3275 .
10.
Pirrung
M.C.
, Chem. Eur. J. , 2006 , 12 , 1312 .
11.
Polshettiwar
V.
, and
Varma
R.S.
, Acc. Chem. Res. , 2008 , 41 , 629 .
12.
Tietze
L.F.
, Chem. Rev. , 1996 , 96 , 115 .
13.
Domling
A.A.
, Chem. Rev. , 2006 , 106 , 17 .
14.
Domling
A.
, and
Ugi
I.
, Angew. Chem., Int. Ed. Engl. , 2000 , 39 , 3169 .
15.
Ugi
I.
, Angew. Chem., Int. Ed. Engl. , 1982 , 21 , 810 .
16.
Tavakolinia
F.
,
Baghipour
T.
,
Hossaini
Z.
,
Zareyee
D.
,
Khalilzadeh
M.A.
, and
Rajabi
M.
, Nucleic Acid Ther. , 2012 , 22 (4 ), 265 .
17.
Vedeje
E.
, and
Krafft
G.A.
, Tetrahedron , 1982 , 38 , 2857 .
18.
Zhang
X.
,
Li
X.
,
Fan
X.
,
Wang
X.
,
Li
D.
,
Qu
G.
, and
Wang
J.
, Mol. Divers. , 2009 , 13 , 57 .
19.
Hossaini
Z.
, and
Rostami-Charati
F.
, J. Appl. Chem. Res. , 2012 , 6 , 48 .
20.
Hilmy Elnagdi
N.M.
, and
Al-Hokbany
N.S.
, Molecules , 2012 , 17 , 4300 .
21.
Fan
X.
,
Wang
X.
,
Zhang
X.
,
Li
X.
, and
Qu
G.
, J. Chem. Res. , 2007 , 3 , 693 .
22.
Tanaka
K.
,
Wada
A.
, and
Noguchi
K.
, Org. Lett. , 2006 , 8 , 907 .
23.
Yamamoto
Y.
,
Takagishi
H.
, and
Itoh
K.
, J. Am. Chem. Soc. , 2002 , 124 , 28 .
24.
Nedolya
N.
,
Brandsma
L.
,
Verkruijsse
H.D.
,
van der Kerk
A.H.T.M.
,
Trofimov
B.A.
, Tetrahedron Lett. , 1998 , 39 , 2631 .
25.
Yavari
I.
,
Hajinasiri
R.
, and
Sayyed-Alangi
S.Z.
, Monatsh Chem. , 2009 , 140 , 205 .
26.
Yavari
I.
,
Hajinasiri
R.
,
Sayyed-Alangi
S.Z.
,
Sajjadi-Ghotbabadi
H.
, Monatsh Chem. , 2009 , 140 , 209 .
27.
Yavari
I.
,
Sayyed-Alangi
S.Z.
,
Sabbaghan
M.
,
Hajinasiril
R.
, and
Iravani
N.
, Monatsh Chem. , 2008 , 139 , 1025 .
28.
Sayyed-Alangi
S.Z.
,
Hossaini
Z.
, and
Rostami-Charati
F.
, Chinese Chem. Lett. , 2012 , 23 , 1119 .