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Reaction of 1-alkynyl thiocyanates with nucleophilic reagents. Synthesis of 2,4-disubstituted 1,3-thiazoles

✍ Scribed by R. L. P. de Jong; J. Meijer; R. S. Sukhai; L. Brandsma

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
454 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Reaction of 1‐alkynyl thiocyanates RC≡C‐S‐C≡N (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 RC≡C‐S‐NR′~2~ (5) (attack on sulfur). With alkoxides R′O^⊖^, the primary attack is on C≡N^•^~•~ the intermediary alkynethiolate RC≡C‐S^⊖^; subsequently reacts with the alkyl cyanate R′OC≡N to afford 1‐alkynyl sulfides RC≡C‐SR′ (6).

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