Iodine Catalyzed Three-component Strecker-type Synthesis of α-Aminonitriles from Aldehydes, Amines and Tributyltin Cyanide
Hong-She Wang
School of Mechatronic Engineering, Beijing Institute of Technology, Beijing 100081, China
Department of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, China
Project supported by the Special Scientific Research Project of Shaanxi Education Commission (No. 02JK054).
Search for more papers by this authorLi-Fang Zhao
Department of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, China
Search for more papers by this authorZhi-Ming Du
School of Mechatronic Engineering, Beijing Institute of Technology, Beijing 100081, China
Search for more papers by this authorHong-She Wang
School of Mechatronic Engineering, Beijing Institute of Technology, Beijing 100081, China
Department of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, China
Project supported by the Special Scientific Research Project of Shaanxi Education Commission (No. 02JK054).
Search for more papers by this authorLi-Fang Zhao
Department of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, China
Search for more papers by this authorZhi-Ming Du
School of Mechatronic Engineering, Beijing Institute of Technology, Beijing 100081, China
Search for more papers by this authorAbstract
A simple and efficient one-pot method has been developed for the synthesis of α-aminonitriles from aldehydes, amines and tributyltin cyanide in the presence of a catalytic amount of iodine with high yields. The reactions proceeded smoothly at room temperature via very simple procedure.
REFERENCES
- 1 Duthaler, R. O.. Tetrahedron, 1994, 50, 1539.
- 2a Weinstock, L. M.; Davis, P.; Handelsman, B.; Tull, R.. J. Org. Chem., 1967, 32, 2823.
- 2b Matier, W. L.; Owens, D. A.; Comer, W. T.; Deitchman, D.; Ferguson, H. C.; Seidehamel, R. J.; Young, J. R.. J. Med. Chem., 1973, 16, 901.
- 3a
Takamura, M.;
Hamashima, Y.;
Usuda, H.;
Kanai, M.;
Shibasaki, M..
Angew. Chem., Int. Ed.,
2000,
39,
1650.
10.1002/(SICI)1521-3773(20000502)39:9<1650::AID-ANIE1650>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
- 3b Porter, J. R.; Wirschun, W. G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H.. J. Am. Chem. Soc., 2000, 122, 2657.
- 3c Sun, P.; Qian, C.; Wang, L.; Chen, R.. Synth. Commun., 2002, 32, 2973.
- 3d Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M.. J. Am. Chem. Soc., 2003, 125, 5634.
- 3e De, S. K.; Gibbs, R. A.. Tetrahedron Lett., 2004, 45, 7407.
- 3f Azizi, N.; Saidi, M. R.. Synth. Commun., 2004, 34, 1207.
- 3g Ohmori, O.; Fujita, M.. Chem. Commun., 2004, 1586.
- 4 Nakamura, S.; Sato, N.; Sugimoto, M.; Toru, T.. Tetrahedron: Asymmetry, 2004, 15, 1513.
- 5a Kobayashi, S.; Busujima, T.; Nagayama, S.. Chem. Commun., 1998, 981.
- 5b
Ishitani, H.;
Komiyama, S.;
Kobayashi, S..
Angew. Chem., Int. Ed.,
1998,
37,
3186.
10.1002/(SICI)1521-3773(19981204)37:22<3186::AID-ANIE3186>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 5c Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S.. J. Am. Chem. Soc., 2000, 122, 762.
- 6 Phukan, P.. Synth. Commun., 2004, 34, 1065.
- 7 Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; zubaidha, P. K.. Tetrahedron Lett., 2004, 45, 9111.
- 8 Phukan, P.. Tetrahedron Lett., 2004, 45, 4785.
- 9 Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K.. Tetrahedron Lett., 2004, 45, 7187.
- 10 Bandgar, B. P.; Bettigeri, S. V.; Joshi, N. S.. Synth. Commun., 2004, 34, 1447.
- 11 Phukan, P.. J. Org. Chem., 2004, 69, 4005.
- 12 Bhat, B. A.; Sahu, D. P.. Synth. Commun., 2004, 34, 2169.
