Synthesis and characterization of stable 2-cyano-2-carboximidic acid alkyl ester-oxiranes and 2, 2-dicarboximidic acid dialkyl ester-oxiranes

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5001-5004

  Hurtaud, Dominique ^a   Baudy Floc'h, Michèle ^a   Le Grel, Philippe ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYANO 2 CARBOXIMIDIC ACID ALKYL ESTER OXIRANE; 2,2 DICARBOXIMIDIC ACID DIALKYL ESTER OXIRANE; ETHYLENE OXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0033516534     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00918-1     Document Type: Article

References (12)

1. Jaime, C.; Ortuno, R.M.; Font, J. J. Org. Chem. 1988, 53, 139-141.
2. Hurtaud, D.; Baudy-Floc'h, M.; Robert, A.; Le Grel, P. J. Org. Chem. 1994, 59, 4701-4703.
3. Florac, C.; Le Grel, P.; Baudy-Floc'h, M.; Robert, A. Synthesis, 1991, 741-743.
4. Baudy-Floc'h, M.; Robert, A. Tetrahedron, 1985, 41, 3297-3303.
5. Payne, G. B. J. Org. Chem. 1961, 26, 663-668.
6. Harrison, J.M.; Inch, T.D. Tetrahedron Lett., 1981, 22, 679-682.
7. 2≠H, or R=iBu). The solvent was then evaporated to give a mixture of Z and E imidates, pure enough to be used in further reaction, in some cases it is possible to separate them by chromatography on silica gel with ether/petroleum ether as eluent.
8. 4Br which was eliminated by filtration. Evaporation of ether gives the imidate 5 E in 95% ratio.
9. -1.
10. 4. Evaporation of the solvent afford the bisimidate 6 which was recrystallized in ether.
11. 3Cl: C, 53.64; H, 4.88; N, 10.43; Cl, 13.19. Found: C, 53.57; H, 4.91; N, 10.31; Cl, 13.21.
12. Pataï, S. The Chemistry of Amidines and Imidates; John Wiley and Sons, London, 1975.