1187-34-4Relevant articles and documents
A multi-component reaction to 5-cyanouracils: Synthesis and mechanistic study
Zhuang, Bo-Ren,Hsu, Gien-Jow,Sung, Kuangsen
, p. 3399 - 3404 (2006)
Acetonitrile as a solvent, excess of primary amines as general bases, and a reflux condition make the multi-component reactions of (2-cyanoacetyl) carbamate 1, ethyl orthoformate, and primary amines form 5-cyanouracils 4a-c feasibly. Mechanistic studies o
Why is the reaction of ethyl (2-cyanoacetyl)carbamate with ethyl orthoformate highly stereoselective?
Sung, Kuangsen,Lin, Ming-Chi,Huang, Pin-Mei,Zhuang, Bo-Ren,Sung, Robert,Wu, Ru-Rong
, p. 1183 - 1189 (2005)
The reaction of ethyl (2-cyanoacetyl)carbamate (1) with ethyl orthoformate in the presence of acetic anhydride is highly stereoselective and only E-ethyl (2-cyano-3-ethoxyacryloyl)carbamate (E-2) is isolated. The reaction is thermodynamically controlled and the product distribution depends on the relative stability between E-2 and Z-2. Both the resonance stabilization of 1.47 kcal mol-1 and the steric hindrance of 2.28 kcal mol-1 in favour of E-2 contribute to the relative stability (3.75 kcal mol-1) between Z-2 and E-2, which is calculated from four isodesmic reactions, and this is the reason why the reaction of compound 1 with ethyl orthoformate is highly stereoselective. The electron-withdrawing ability of some substituents was evaluated. The sequence of π-accepting ability is C(O)NHC(O)OEt > C(O)NH2 > CN and the sequence of σ-accepting ability is CN > C(O)NHC(O)OEt > C(O)NH2. Copyright
AZABICYCLO [3. 1. 0] HEXYL DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS
-
Page/Page column 79, (2008/06/13)
The present invention relates to novel compounds of formula (I)' or a salt thereof: wherein G is selected from a group consisting of: phenyl, a 5- or 6-membered monocyclic heteroaryl group, or a 8- to 11 -membered heteroaryl bicyclic group; A is a group P