Abstract
The 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ from isatin and sarcosine with 5-arylmethylene-3-phenyl-2-thioxothiazolidin-4-one in refluxing toluene produced the 2″-thioxodispiro[indole-3,2′-pyrrolidine-3′,5″-[1,3]thiazolidine]-2,4″-dione derivatives in good yields (80–88%). The structures were assigned by 1H NMR, IR, elementary analysis and single crystal X-ray diffraction analysis through which the cycloaddition reaction was found to be highly regio- and stereo-selective.
Keywords
References
1.
Huisgen
R.
, Angew. Chem. Int. Ed. Engl. , 1963 , 2 , 565 .
2.
Grzegorz
M.
,
Emilia
O.
,
Małgorzata
C.
,
Verena
M.
,
Anthony
L.
, and
Heinz
H.
, J. Fluorine Chem. , 2014 , 165 , 27 .
3.
Kawashima
K.
,
Kakehi
A.
, and
Noguchi
M.
, Tetrahedron , 2007 , 63 , 1630 .
4.
Woodward
R.B.
, and
Hoffmann
R.
, Angew. Chem. Int. Ed. Engl. , 1969 , 8 , 781 .
5.
Shanmugavel
U.M.
,
Subbu
P.
, and
Abdulrahman
A. I.
, Tetrahedron. Lett. , 2012 , 53 , 349 .
6.
Koumbisv
A.E.
, and
Gallos
J. K.
, Curr. Org. Chem. , 2003 , 7 , 771 .
7.
Sannigrahi
M.
, Tetrahedron , 1999 , 55 , 9007 .
8.
James
D.M.
,
Kunze
H. B.
, and
Faulkner
D. J.
, J. Nat. Prod. , 1991 , 54 , 1137 .
9.
Kobayashi
J.
,
Tsuda
M.
,
Agemi
K.
,
Shigemiri
H.
,
Ishibashi
M.
,
Sasaki
T.
, and
Mikami
Y.
, Tetrahedron , 1991 , 47 , 6617 .
10.
Deng
J.
,
Mo
L. P.
,
Zhao
F. Y.
,
Zhang
Z. H.
, and
Liu
S. X.
, ACS Comb. Sci. , 2012 , 14 , 335 .
11.
Guo
R.Y.
,
Wang
P.
,
Wang
G. D.
,
Mo
L. P.
, and
Zhang
Z. H.
, Tetrahedron , 2013 , 69 , 2056 .
12.
Jossang
A.
,
Jossang
P.
,
Hadi
H. A.
,
Sevenet
T.
, and
Bodo
B.
, J. Org. Chem. , 1991 , 56 , 6527 .
13.
Galliford
C.V.
, and
Scheidt
K. A.
, Angew. Chem. Int. Ed. , 2007 , 46 , 8748 .
14.
James
M.N. G.
, and
Williams
G. J. B.
, Can. J. Chem. , 1972 , 50 , 2407 .
15.
Cui
C.B.
,
Kakeya
H.
, and
Osada
H.
, Tetrahedron , 1996 , 52 , 12651 .
16.
Sebahar
P.R.
, and
Williams
R. M.
, J. Am. Chem. Soc. , 2000 , 122 , 5666 .
17.
Kang
T.H.
,
Matsumoto
K.
,
Murakami
Y.
,
Takayama
H.
,
Kitajima
M.
,
Aimi
N.
, and
Watanabe
H.
, Eur. J. Pharmacol. , 2002 , 444 , 39 .
18.
Garcia Prado
E.
,
Garcia Gimenez
M. D.
,
De la Puerta Vazquez
R.
,
Espartero Sanchez
J. L.
, and
Saenz Rodriguez
M. T.
, Phytomedicine , 2007 , 14 , 280 .
19.
Balamurugan
K.
,
Jeyachandran
V.
,
Perumal
S.
, and
Menéndez
J. C.
, Tetrahedron , 2011 , 67 , 1432 .
20.
Kumar
R.R.
, and
Perumal
S.
, Tetrahedron , 2007 , 63 , 7850 .
21.
Feng
G.L.
,
Zhang
H. L.
, and
Geng
L. J.
, J. Chem. Res. , 2011 , 35 , 121 .
22.
Feng
G.L.
,
Zhang
H. L.
, and
Geng
L. J.
, J. Chem. Res. , 2014 , 38 , 283 .
23.
Feng
G.L.
,
Li
Y.
,
Chen
S. R.
,
Geng
L. J.
, and
Wang
K. F.
, J. Chem. Res. , 2014 , 38 , 589 .
24.
Seyfried
M.S.
,
Linden
A.
,
Mloston
G.
, and
Heimgartner
H.
, Pol. J. Chem. , 2006 , 80 , 1363 .
25.
Cherbuliez
E.
,
Marszalek
J.
, and
Rabinowitz
J.
, Helv. Chim. Acta , 1964 , 47 , 1666 .