CLC number: O622.6
On-line Access: 2024-08-27
Received: 2023-10-17
Revision Accepted: 2024-05-08
Crosschecked: 0000-00-00
Cited: 0
Clicked: 4970
CHEN Jue, ZHANG Yong-min. Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives[J]. Journal of Zhejiang University Science A, 2004, 5(2): 218-221.
@article{title="Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives",
author="CHEN Jue, ZHANG Yong-min",
journal="Journal of Zhejiang University Science A",
volume="5",
number="2",
pages="218-221",
year="2004",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2004.0218"
}
%0 Journal Article
%T Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives
%A CHEN Jue
%A ZHANG Yong-min
%J Journal of Zhejiang University SCIENCE A
%V 5
%N 2
%P 218-221
%@ 1869-1951
%D 2004
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2004.0218
TY - JOUR
T1 - Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives
A1 - CHEN Jue
A1 - ZHANG Yong-min
J0 - Journal of Zhejiang University Science A
VL - 5
IS - 2
SP - 218
EP - 221
%@ 1869-1951
Y1 - 2004
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2004.0218
Abstract: Samarium and a catalytic amount of iodine were used to obtain functionalized cyclopentenes by reductive dimerization followed by intramolecular cyclization of 1,1-dicyanoalkenes under mild conditions.
[1] Cook, A.G., 1969. Enamines: Their Synthesis, Structure and Reaction. Marcel Dekker, New York.
[2] Fan, X.S., Zhang, Y.M., 2001. Reductive cyclodimerization ofα,β-unsaturated ketones promoted by AlCl3/Sm system: a facile synthesis of 2-aroyl-1,3,3-triaryl cyclopentanol derivatives.Chin. J. Chem.,19(6):616-619(in Chinese).
[3] Helmers, R., Kaiser, W., 1971. Ueber eine alkylierende retro-thorpe-reaktion.Tetrahedron Lett.,12:3853-3855.
[4] Huang, Y., Zhang, Y.M., 1997. Preparation of disulfides by reduction of sodium alkyl thiosulfates with metallic samarium and catalytic amount of iodine.Synth. Commun.,27(6):1043-1047.
[5] Huang, Y., Zhang, Y.M., Wang, Y.L., 1997. Facile reduction of azides to the corresponding amines with metallic samarium and catalytic amount of iodine.Tetrahedron Lett.,38(6):1065-1066.
[6] Molander, G.A., 1992. Application of lanthanide reagents in organic synthesis.Chem. Rev.,92(1):29-68.
[7] Molander, G.A., Harris, C.R., 1996. Sequencing reactions with samarium(II) iodide.Chem. Rev.,96(1):307-338.
[8] Ogawa, A., Nanke, T., Takami, N., Takam, Y., 1994. Enhanced reducing ability by the combination of SmI2 and Sm metal in the reduction of alkyl halides.Chem. Lett., (2):379-380.
[9] Seitz, G., Monnighoff, H., 1971. Die thorpe-ziegler-cyclisi-erung zur synthese von substituierten cyclopenta thiophene.Tetrahedron Lett.,12:4889-4890.
[10] Stork, G., Brizzolaro, A., Landesman, H., Szmuszkovicz, J., Terrel, R., 1963. The enamine alkylation and acylation of carbonyl compounds.J. Am. Chem. Soc.,85:207-222.
[11] Yanada, R., Negoro, N., Okaniwa, M., Ibuka, T., 1999. Diastereoselective allylation and albylation of optically active imines with metallic samarium and a catalytic amount of iodide.Tetrahedron,55(49):13947-13956.
[12] Zhong, W.H., Zhang, Y.M., 2000. Samarium diiodide mediated simultaneous reduction of nitro group and azide group in o-nitrophenylazide: a new access to 2,3-dihydro-1H-1,5-benzodiazepines.J. Chem. Res., (8):532-534.
[13] Zhou, L.H., Zhang, Y.M., 1997. A novel cyclodimerization of Arylidenecyanoacetate promoted by samarium diiodide.Tetrahedron Lett.,38(46):8063-8066.
[14] Zhou, L.H., Zhang, Y.M., 1998. A novel reductive cyclization of arylmethyllidenemalononitrile promoted by samarium diiodide.J. Chem. Soc., Perkin Trans.I, (15):2399-2402.
Open peer comments: Debate/Discuss/Question/Opinion
<1>