Reaction of Benzoxa(thia)zoles with Allenylmagnesium Bromide: Synthesis of Propargylbenzothiazolines and Dipropargylalkyl-o-aminophenols

Article abstract of DOI:10.1055/s-1986-31727

Benzoxazoles 2a-e and benzothiazole 4a react with the Grignard reagent prepared from propargyl bromide to give the N-dipropargylalkyl-o-aminophenols 3a-e and the N-dipropargylalkyl-o-aminothiophenol as disulfide 6 respectively.The reaction of benzothiazoles 4b-e with 1 gives the propargylbenzothiazolines 5b-e and that of 2-methoxybenzothiazole 8 produces the 2-allenylbenzothiazole 9.