2-Aryl-N-tosylazetidines as Formal 1,4-Dipoles for [4 + 2] Cycloaddition Reactions with Nitriles: An Easy Access to the Tetrahydropyrimidine Derivatives
Organic Letters2004Vol. 6(26), pp. 4829–4831
Citations Over TimeTop 10% of 2004 papers
Abstract
[reaction: see text] A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitriles in the presence of BF3.OEt2 has been described for the synthesis of substituted tetrahydropyrimidines. It is proposed that the reaction proceeds in Ritter fashion.
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