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PubMed · 5333309

Mefenamic acid.

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1966-12-17. Mefenamic acid.. https://pubmed.ncbi.nlm.nih.gov/5333309/

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Efficient syntheses of thiochromans via cationic cycloadditions.

alpha-(Benzotriazolyl)methyl thioethers 1a-e reacted with styrenes under Lewis acid catalysis to give novel polysubstituted thiochromans (3,4-dihydro-2H-1-benzothiopyrans) 3-14 and 16-20 in generally high yields. Most thiochromans were isolated as one diastereomer following recrystallization. The configuration and conformation of the products are predicted on the basis of their NMR data. A stepwise reaction, proceeding via a [4(+) + 2] cationic polar cycloaddition mechanism, is proposed.

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