Abstract
The oxoketene dithioacetals 1 undergo regioselective 1,2-addition with 2-lithiomethyl-4-methylthiazole ( 2a ) and 2-lithiomethylthiazoline (3) to afford the carbinol acetals 4 which on borontrifluoride etherate assisted cyclization yield the corresponding substituted and annelated 3-methyl-5- methylthiothiazolo[3,2-a.] pyridinium tetrafluoroborates ( 5a - g , 8a , b , 10 , 12 ) and the dihydro derivatives ( 23 - 25 ) respectively in good yields. The corresponding 2-methyl-5-phenylthiazole ( 16 ) however underwent both nuclear and side chain deprotonation and yielded a mixture of products under similar reaction conditions.
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