A Study on the Reaction of 1-(3-Pyridyl)-2,2-di-substituted Ethylenes with 1-Benzyl-1,4-dihydronicotinamide
Hua-Jian Xu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorYou-Cheng Liu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
College of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Tel.: 0086-0551-3603254; Fax: 0086-0551-3603254
Search for more papers by this authorYao Fu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorHua-Jian Xu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorYou-Cheng Liu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
College of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Tel.: 0086-0551-3603254; Fax: 0086-0551-3603254
Search for more papers by this authorYao Fu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorAbstract
The reaction of a series of 1-(3-pyridyl)-2,2-di-substituted ethylenes with 1-benzyl-1,4-dihydronicotinamide (BNAH) in deaerated acetonitrile produces the corresponding 1-(3-pyridyl)-2,2-di-substituted ethanes in contrast to benzylidenemalononitrile (BM) which does not react with BNAH under the same conditions.
REFERENCES
- 1a Strout, D. M.; Meyers, A. I.. Chem. Rev., 1982, 82, 223.
- 1b Westheimer, F. H., In Pyridine Nucleotide Coenzymes: Chemical, Biochemical, and Medical Aspects. Eds.: D. Dolphin; R. Poulson; O. Avramovic. Wiley-Interscience, New York, 1988, Part A, p. 253.
- 1c Bunting, J. W.. Bioorg. Chem., 1991, 19, 456.
- 2a Norcross, B. E.; Klinedeinst, P. E.; Westheimer, E. H.. J. Am. Chem. Soc., 1962, 84, 797.
- 2b
Ohno, N.;
Tamura, R.;
Kaji, A..
J. Am. Chem. Soc.,
1980,
102,
2851.
10.1021/ja00528a062 Google Scholar
- 2c Chipman, D. M.; Yanivand, R.; Van Eikeren, P.. J. Am. Chem. Soc., 1980, 102, 3244.
- 2d Ohno, N.; Tamura, R.; Kaji, A.. J. Am. Chem. Soc., 1983, 105, 4017.
- 2e Powell, M. F.; Bruice, T. C.. J. Am. Chem. Soc., 1983, 105, 7139.
- 2f Carlson, B. W.; Miller, L. L.; Neta, P.; Gradkowski, J.. J. Am. Chem. Soc., 1984, 106, 7233.
- 2g Tanner, D. D.; Kharrat, A.. J. Am. Chem. Soc., 1988, 110, 2968.
- 2h Fukuzumi, S.; Mochizuki, S.; Tanaka, T.. J. Am. Chem. Soc., 1989, 111, 1497.
- 2i Anne, A.; Moirou, J.; Saveant, J. M.. J. Am. Chem. Soc., 1993, 115, 10224.
- 2j Bunting, J. W.; Chew, V. S. F.; Chu, G.. J. Org. Chem., 1982, 47, 2303.
- 2k Bunting, J. W.; Chew, V. S. F.; Chu, G.. J. Org. Chem., 1982, 47, 2308.
- 2l Zhu, X.-Q.; Liu, Y.-C.. J. Org. Chem., 1998, 63, 2786.
- 2m Cheng, J.-P.; Lu, Y.; Zhu, X.-Q.; Mu, L. J.. J. Org. Chem., 1998, 63, 6108.
- 2n Zhu, X.-Q.; Liu, Y.-C.; Wang, H.-Y.; Wang, W.. J. Org. Chem., 1999, 64, 8982.
- 2o Dai, D.-M.; Liu, Y.-C.; Li, J.. Chin. J. Chem., 2001, 19, 1217.
- 3 Pross, A.. Acc. Chem. Res., 1985, 18, 212.
- 4 Verhoeven, J. W.; Gerresheim, W.; Martens, F. M.; Kerk, S. M.. Tetrahedron, 1986, 42, 975.
- 5 Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J. M.. J. Am. Chem. Soc., 1992, 114, 4694.
- 6
Liu, Y.-C.;
Wang, H.-Y.;
Yang, Q.-C.;
Mak, T. C. W..
J. Chem. Soc., Perkin Trans. 2,
2000,
649.
10.1039/a909716c Google Scholar
- 7 Xu, H.-J.; Dai, D.-M.; Liu, Y.-C.; Li, J.; Luo, S.-W.; Wu, Y.-D.. Tetrahedron Lett., 2005, 46, 5739.
- 8 Wang, H.-Y.; Liu, Y.-C.; Zhu, X.-Q.; Guo, Q.-X.. Chin. J. Chem., 1999, 17, 184.
- 9 McMurry, J., Organic Chemistry, 6th ed., Thomson-Brooks/Cole, Belmont, 2004, p. 1065.
- 10 Wang, H.-Y.; Dai, D.-M.; Liu, Y.-C.; Guo, Q.-X.. Tetrahedron Lett., 2002, 43, 7527.
- 11a Case, R. A.; Pandit, U. K.. J. Am. Chem. Soc., 1979, 101, 7059.
- 11b Li, B.; Liu, Y.-C.; Guo, Q.-X.. J. Photochem. Photobiol. A, 1997, 103, 101.
- 12 Anderson, A. G.; Hammer, J. B.; Hammer, G. B.. J. Am. Chem. Soc., 1958, 81, 992.
- 13a Bigi, F.; Conforti, M. L.; Maggi, R.; Piccinno, A.; Sartori, G.. Green Chem., 2000, 2, 101.
- 13b Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Visali, B.; Narsaiah, A. V.; Nagaiah, K.. Eur. J. Org. Chem., 2004, 546.
- 13c Mimura, T.; Nakamura, Y.; Nishino, J.; Sawayama, T.; Komiya, T.; Deguchi, T.; Kita, A.; Nakamura, H.; Matsumoto, J.. J. Med. Chem., 1992, 35, 602.
