- Substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents: a route to allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals
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The substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents has been examined in a search for new methods of preparing functional acetals.The efficiency of the substitution of the acetoxy group is highly dependent on the nature of the organometallic reagents: soft nucleophiles with strong electrophilic assistance by the counterion are the best reagents.Allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals have been made by this route, in which dialkoxymethylacetates often function as useful substitutes for dialkylphenylorthoformates.
- Beaudet, Isabelle,Duchene, Alain,Parrain, Jean-Luc,Quintard, Jean-Paul
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p. 201 - 212
(2007/10/02)
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- Benzyl cyanoacetals
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Benzyl cyanoacetals of formula: STR1 wherein R1, R2 and R3 are the same or different and each is a halogen or a hydrogen atom, an alkoxy group, an alkyl group, or a dialkylamino group; R4 is an alkoxycarbonyl group, or an aldehyde group; And R5 is an alkyl group; the alkyl or alkoxy groups each having from 1 to 4 carbon atoms, and their use as intermediates in the preparation of antibacterial 2,4-diamino-5-benzylpyrimidines. They are prepared from a reaction between an orthoester and an α-substituted-β-benzylpropionitrile and then the resulting cyanoacetal is converted to the benzyl-pyrimidine by reaction with guanidine.
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