Additions of 1-(α-Aminoalkyl)benzotriazoles to N-Vinylamines and N-Vinylamides. A Novel and Versatile Method for the Preparation of Unsymmetrically Substituted 1,3-Diamines

Article abstract of DOI:10.1021/jo00097a023

Additions of N,N-dialkyl-1H-benzotriazole-1-methanamines 1 to 9-vinylcarbazole followed by reduction of the adducts with lithium aluminum hydride gave the corresponding 9-(3-(dialkylamino)propyl)carbazoles 8 in good yield.Treatment of the adducts with Grignard reagents gave products 9 with an alkyl or aryl group at the C-1 atom of the propylene linkage.Use of α-phenyl-N,N-dialkyl-1H-benzotriazole-1-methanamine (14) in the addition led to the C-3 phenyl substituted products 15-18.Similar additions to N-vinyl-N-methylacetamide or 1-vinyl-2-pyrrolidinone followed by reduction of the adducts gave unsymmetrically substituted 1,3-propanediamines.Triamine 36 was obtained by condensation of ethylamine with formaldehyde and benzotriazole, addition of the product to 1-vinylpyrrolidinone, and reduction of the adduct with lithium aluminum hydride. 1,3-Propanediamine used in this process gave hexahydropyrimidine 39 while 1,6-hexanediamine gave hexamine 42.