Studies on the Anodic Cyanation Reaction to Synthesize α-Aminonitriles

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (8): 916-922. Previous Articles Next Articles

α-氨基腈的阳极氰化合成反应研究

赵萍^a, 尹应武^*,a,b

^a清华大学化学系北京 100084
^b清华紫光英力化工技术有限责任公司北京 100084

收稿日期:2003-05-08 修回日期:2003-12-05 接受日期:2004-03-04 发布日期:2022-09-20
通讯作者: * E-mail: ywy@mail.insight.net.cn; Fax: 010-62793514.
基金资助:
清华紫光英力化工技术有限责任公司资助项目.

Studies on the Anodic Cyanation Reaction to Synthesize α-Aminonitriles

ZHAO Ping^a, YIN Ying-Wu^*,a,b

^aDepartment of Chemistry, Tsinghua University, Beijing 100084
^bBeijing TH-UNIS Insight Co., Ltd. Beijing 100084

Received:2003-05-08 Revised:2003-12-05 Accepted:2004-03-04 Published:2022-09-20

Abstract

Six-membered cyclic α-aminonitriles were prepared fromanodic cyanation of N-benzylpiperidine. Low current, CH₃OH/H₂O and CH₃CN/H₂O used as solvent, tetraammonia salt such as Et₄NOTs and Et₄NBr used as surfactant are propitious to the reaction under constant current electrolysis. Graphite as anode can give the similar result to platinum. The potentiostatelectrolytic condition of 0.9～1.4 V (vs. SCE), low temperature and low substrate concentration offered good yields (above 90%) of α-aminonitriles. Themechanism of the reaction was studied and the amount of isomers was depended onthe adsorption status at the anode surface and stability of intermediate was also studied under potentiostat electrolysis.

Key words: anodic cyanation, electrolysis, N-benzylpiperidine, α-aminonitrile

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ZHAO Ping, YIN Ying-Wu. Studies on the Anodic Cyanation Reaction to Synthesize α-Aminonitriles[J]. Chinese Journal of Organic Chemistry, 2004, 24(8): 916-922.

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References

1 Nazabadioko, S.; Perez, T. J.; Brieva, R.; Gotor, V. Tetrahedron: Asymmetry 1998, 9, 1597.
2 Koskinen, A.; Lounasmaa, M.; Tetrahedron 1983, 39, 1627.
3 Stork, G.; Ozorio, A. A.; Leong, A. Y. W. Tetrahedron Lett.1978, 19, 5175.
4 Husson, H.-P. Indole and Biogenetically Related Alkaloids,Academic Press, London, 1983.
5 Ahlbrecht, H.; Raab, N.; Vonderheid, C. Synthesis 1979, 127.
6 Yamada, S.-I.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1976, 17, 66.
7 Bonin, M.; Romero, J. R.; Gerierson, D. S.; Husson, H. P. Tetrahedron Lett. 1982, 23, 3369.
8 Bonin, M.; Besselievre, R.; Grierson, D. S.; Husson, H. P. Tetrahedron Lett. 1983, 24, 1493.
9 Royer, J.; Husson, H. P. J. Org. Chem. 1985, 5, 670.
10 Zhu, Z.; Quirion, J. C.; Husson, H. P. Tetrahedron Lett. 1989, 30, 5137.
11 Grierson, D. S.; Bettiol, J. L.; Buck, I.; Husson, H. P. J. Org. Chem. 1992, 57, 6414.
12 Potier, P. Rev. Latinoam. Quim. 1978, 9, 47.
13 Grierson, D. S.; Harris, M.; Husson, H.-P. J. Am. Chem. Soc. 1980, 102, 1064.
14 Santamaria, J.; Kaddachi, M. T.; Rigaudy, J. Tetrahedron Lett. 1990, 31, 4735.
15 Santamaria, J.; Kaddachi, M. T.; Ferroud, C. Tetrahedron Lett. 1992, 33, 781.
16 Sayre, L. M.; Engrlhart, D. A.; Venkataraman, B.; Babu, M. K. M.; Mccoy, G. D. Biochem. Biophys. Res. Commun. 1991, 179, 1368.
17 Chiba, T.; Takata, Y. J. Org. Chem. 1977, 42, 2973.
18 Le Gall, E.; Hurvois, J.-P.; Renaud, T.; Moinet, C.; Tallec, A.; Uriac, P. U.; Sinbandhit, S.; Toupet, L. Liebigs Ann./Recl. 1997, 2089.
19 Le Gall, E.; Malassene, R.; Toupet, L.; Hurvois, J.-P.; Moinet, C. Synlett 1999, 1686.
20 Le Gall, E.; Hurvois, J.-P.; Sinbandhit, S. Eur. J. Org. Chem. 1999, 2645.
21 Yang, T.-K.; Yeh, S.-T.; Lay, Y.-Y. Heterocycles 1994, 38, 1711.
22 Andreades, S.; Zahnow, E. W. J. Am. Chem. Soc. 1969, 91, 4181.
23 Portis, L. C.; Klug, J. T.; Mann, C. K. J. Org. Chem. 1974, 39, 3488.
24 Masui, M.; Sayo, H. J. Chem. Soc. B 1971, 1593.
25 Michel, S.; Le Gall, E.; Hurvois, J.-P.; Moinet, C.; Tallee, A.; Uriac, P.; Toupet, L. Liebigs Ann./Recl. 1997, 259.

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α-氨基腈的阳极氰化合成反应研究

Studies on the Anodic Cyanation Reaction to Synthesize α-Aminonitriles

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