2-aryl-N-tosylazetidines as formal 1,4-dipoles for [4 + 2] cycloaddition reactions with nitriles: an easy access to the tetrahydropyrimidine derivatives.
[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.
Prasad
B A Bhanu
BA
Department of Chemistry, Indian Institute of Technology, Kanpur, 208 016, India.
Bisai
Alakesh
A
Singh
Vinod K
VK
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism
D001384:Azetidines; D009570:Nitriles; D011743:Pyrimidines