Direct vinylation of 2-substituted N-(benzylidene)glycinonitriles under basic conditions

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8909-8912

  Jończyk, Andrzej ^b   Pakulski, Zbigniew ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b Technical University Politechnika   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030566839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02045-X     Document Type: Article

References (19)

1. 2. Rubio, A.; Ezquerra, J. Tetrahedron Lett., 1995, 36, 5823-5826.
2. 3. López, A.; Moreno-Manas, M.; Pleixats, R.; Roglans, A.; Ezquerra, J.; Pedregal, C. Tetrahedron, 1996, 52, 8365-8386.
3. 4. 1a (oil, yield 93%) and 1b (oil, yield 81%) were prepared as described for similar compounds (Stork, G.; Leong, A. Y. W.; Touzin, A.M. J. Org. Chem., 1976, 41, 3491-3493), and fully characterized.
4. 5 Tsuge, O.; Ueno, K.; Kanemasa, S.; Yorozu, K. Bull. Chem. Soc. Jpn., 1986, 59, 1809-1824.
5. 6 Ma̧kosza, M.; Czyzewski, J.; Jawdosiuk, M. Org. Synth., 1976, 55, 99-102.
6. 7. Jończyk, A.; Lipiak, D.; Zdrojewski, T. Tetrahedron, 1990, 46, 1025-1038.
7. 8 Zdrojewski, T.; Jończyk, A. Liebigs Ann. Chem., 1993, 375-378 and literature cited therein.
8. 9 Dehmlow, E.V.; Dehmlow, S.S. PhaseTransfer Catalysis, 3rd ed., Verlag Chemie, Weinheim, 1993.
9. 10. Starks, C.M.; Liotta, C.; Halpern, M. Phase Transfer Catalysis - Fundamentals, Applications and Industrial Perspectives, Chapman & Hall, New York, 1994.
10. 3, tetrabutylammonium bromide as a catalyst, in acetonitrile solution (reflux, 6 h) none of 6a was formed.
11. 6 All compounds gave satisfactory HR-MS.
12. 3).
13. 14. Observed regiochemistry of addition of nucleophiles to 4 has been explained by the following polarization (Krishnamurthy, V.N.; Soundararajan, S. J. Org. Chem., 1966, 31, 4300-4301):
14. 15. α-Amino acids synthesis: O'Donnell, M.J. (Ed.), Tetrahedron, 1988, 44, 5253-5614.
15. 16. Albright, J.D. Tetrahedron, 1983, 39, 3207-3233.
16. 17. Arseniyadis, S.; Kyler, K.S.; Watt, D.S. Organic Reactions, John Wiley & Sons, 1984, 31.
17. 2O - very slow, practically unuseful process; hydrolysis of 6a,b by 1M HCl / hexane - formation of tars, already in room temp.; hydrolysis of 6a,b by 20% NaOH in water or methanol at r.t. - unchanged substrate.
18. 2O (13.5 mM) and water (10 mL) was refluxed for 1 h. Filtration followed by evaporation and column chromatography (hexane - ethyl acetate, 10 : 1) gave 8b (85%).
19. 3).