13831-08-8Relevant academic research and scientific papers
Reactions of 1-alkynyl thiocyanates with nucleophilic reagents. Synthesis of 2,4-disubstituted 1,3-thiazoles
Jong, R.L.P. de,Meijer, J.,Sukhai, R.S.,Bradsma, L.
, p. 310 - 313 (2007/10/02)
Reaction of 1-alkynyl thiocyanates RCC-S-CN (1) with alcohols, phenol or thiols or secondary aliphatic amines in the presence of anhydrous zinc chloride or boron trifluoride diethyl etherate gives mixtures of 2,4-disubstituted 1,3-thiazoles (2), thiocarbonyl compounds (3) (thiono esters, dithio esters or thioamides) and 2-alkylidene-1,3-dithioles (4).In all cases, the 1,3-thiazoles can be obtained in good yields if the proper reaction conditions are applied.Interaction between 1 and lithium dialkylamides LiNR'2 gives the compounds RCC-S-NR'2 (5) (attack on sulfur).With alkoxides R'O1-, the primary attack is on CN: the in termediacy alkynethiolate RCC-S1- subsequently reacts with the alkyl cyanate R'OCN to afford 1-alkynyl sulfides RCC-SR'(6)
