New potentially bacteriostatic and fungistatic agents on the basis of 5-methoxypent-4-en-2-yn-1-one or -1-imine

Article abstract of DOI:10.1002/ardp.19833160513

Carboxylic chlorides, imidoyl chlorides and chloroformamidines react smoothly with 1-methoxy-but-1-en-3-yne on catalysis with copper (I) iodide/bis(triphenylphosphine)palladium dichloride in triethylamine to yield the α-acetylene ketones and α-acetylenimines 1-23. No reaction occurs between 5-methoxypent-4-en-2-yn-1-one (1) and nucleophiles. Under the conditions of the bromine addition the divinyllactol 24 arises. With thiobenzamide, 1 gives 2,3a-diphenyl-3aH-pyrano[2,3-d]thiazole (25).