Allenes. Part 40. 2:1 Bis-adducts from allenic nitriles and phenylpropynenitriles with difunctional nucleophiles and their conversion into heterocycles

Abstract

Two equivalents of allenic nitrile or phenylpropynenitrile add to 1,2- and 1,3-diamines, 2-aminoethanethiol, ethanedithiol, and 4-aminopyridine to give 2:1 adducts of structures (2), (4), and (5). Ring closure and elimination of one equivalent each of allenic nitrile (or phenylpropynenitrile) and acetonitrile gave the imidazolines (29), the thiazolines (30), and the tetrahydropyrimidines (31). Mass spectral fission patterns are discussed.