Reactions of <i>N</i>‐heteroarylformamide oximes and <i>N</i>‐heteroarylacetamide oximes with <i>N,N</i>‐dimethylformamide dimethyl acetal. Synthesis of 2‐methyl‐<i>s</i>‐triazolo[1,5‐<i>x</i>]azines and <i>N</i>‐methylcyanoaminoazines

Abstract

Abstract N ‐Heteroarylformamide oximes 3 (R  H) were converted with N,N ‐dimethylformamide dimethyl acetal (DMFDMA) into N ‐heteroaryl‐ N ‐methylcyanoamino compounds 5 , as the main products. In some instances N ‐heteroarylcyanoamino compounds 4 , cyanoimino compounds 7 , and some other products, such as 9 and 10 were also formed. On the other hand, N ‐heteroarylacetamide oximes 3 (R  CH 3 ) were cyclized under the same reaction conditions into 2‐methyl‐ s ‐triazolo[1,5‐ x ]azines ( 6 ). N ‐Heteroarylacetamide O ‐methyl oximes 11 and 12 were prepared from the corresponding acetamidines 2 (R  CH 3 ) and O ‐methylhydroxylamine.