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CLC number: O622.6
On-line Access: 2024-08-27
Received: 2023-10-17
Revision Accepted: 2024-05-08
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Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4
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Li Xue, Zhang Yong-Min. Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4[J]. Journal of Zhejiang University Science B, 2006, 7(3): 198-201.
@article{title="Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4",
author="Li Xue, Zhang Yong-Min",
journal="Journal of Zhejiang University Science B",
volume="7",
number="3",
pages="198-201",
year="2006",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2006.B0198"
}
%0 Journal Article
%T Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4
%A Li Xue
%A Zhang Yong-Min
%J Journal of Zhejiang University SCIENCE B
%V 7
%N 3
%P 198-201
%@ 1673-1581
%D 2006
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2006.B0198
TY - JOUR
T1 - Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4
A1 - Li Xue
A1 - Zhang Yong-Min
J0 - Journal of Zhejiang University Science B
VL - 7
IS - 3
SP - 198
EP - 201
%@ 1673-1581
Y1 - 2006
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2006.B0198
Abstract: amides can be obtained in good to excellent yield by sm/TiCl4 mediated reductive cleavage of N=N bond in azo compounds and successive acylation in one pot. It offers an alternative method for the synthesis of amides from very simple starting materials directly.
[1] Banik, B.K., 2002. Samarium metal in organic synthesis. Eur. J. Org. Chem., 2002(15):2431-2444.
[2] Chen, J., Zhang, Y., 2004. Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives. J. Zhejiang Univ. SCI, 5(2):218-221.
[3] Donaruma, L.G., Heldt, W.Z., 1960. The Beckmann rearrangement. Org. React., 11:2-36.
[4] Gawley, R.E., 1988. The Beckmann reactions: rearrangement, elimination-additions, fragmentations, and rearrangement-cyclizations. Org. React., 35:14-24.
[5] Gilchrist, T.L., 1991. Reductions of N=N, N-N, N-O and O-O bonds. In: Trost, B.M., Fleming, I. (Eds.), Comprehensive Organic Synthesis. Pergamon Press, Oxford, 8:381-402.
[6] Girard, P., Namy, J.L., Kagan, H.B., 1980. Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents. J. Am. Chem. Soc., 102(8):2693-2698.
[7] Krief, A., Laval, A.M., 1999. Coupling of organic halides with carbonyl compounds promoted by SmI2, the Kagan reagent. Chem. Rev., 99(3):745-778.
[8] Li, Z.F., Zhang, Y.M., 2000. Facile synthesis of amidines via intermolecular reductive coupling of nitriles with azobenzene promoted by samarium diiodide. Chin. Chem. Lett., 11:495-498.
[9] Molander, G.A., 1998. Diverse methods for medium ring synthesis. Acc. Chem. Res., 31(10):603-609.
[10] Molander, G.A., Harris, C.R., 1996. Sequencing reactions with samarium (II) iodide. Chem. Rev., 96(1):307-338.
[11] Molander, G.A., Harris, C.R., 1998. Sequenced reactions with samarium (II) iodide. Tetrahedron, 54(14):3321-3354.
[12] Movassagh, B., Meibodi, F., Sobhani, S., 2002. Facile reparation of amides from thioamides by ceric ammonium nitrate. Indian J. of Chem., 41B:1296-1298.
[13] Souppe, J., Danon, L., Namy, J.L., Kagan, H.B., 1983. Some organic reactions promoted by samarium diiodide. J. Organomet. Chem., 250(1):227-236.
[14] Zhang, Y.M., Lin, M.Q., Yu, Y.P., 2004. A novel reduction of diketones with i-RMgBr catalyzed by Cp2Ti2Cl2 and deoxygenation of sulfoxides by Cp2Ti2Cl2/Al system. J. Zhejiang Univ. SCI, 5:1175-1179.
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