Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds

Abstract

Nucleophiles from deprotonation of diazomethyl compounds having diverse electron withdrawing groups react with 4-carboxylato-1,2,3-triazines at the 6-position to extrude dinitrogen and produce diazovinylketoesters compounds with five or six linear contiguous sp²-hybridized carbons, whereas these same nucleophiles react with 4-carboxylato-1,2,3-triazine 1-oxides, also at the 6-position, to form pyrazolines with the expulsion of nitrous oxide and cyanocarboxylate. This disparity is due to the significant difference in reactivity of the nucleophilic addition products.