Preparation of 2,3-dihydrothiazolo[2,3-a]isoquinolinium salts and their reactions with complex metal hydrides
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1799-1803
- https://doi.org/10.1039/p19720001799
Abstract
3-Methyl-2,3-dihydrothiazolo[2,3-a]isoquinolinium perchlorate (3; R = Me) has been synthesised by the cyclisations of 1-allylthioisoquinoline (1) and β-hydroxypropylthioisoquinoline (4; X = H, OH; R = Me). 2,3-Dihydrothiazolo[2,3-a]isoquinolinium perchlorate (3; R = H) was obtained from β-hydroxyethylthioiso-quinoline (4; X = H, OH; R = H) as well as 1-mercaptoisoquinoline and ethylene dibromide. Reduction of 3-methyl-2,3-dihydrothioazolo[2,3-a]isoquinolinium perchlorate (3; R = Me) and 3-methylthiazolo[2,3-a]isoquinolinium perchlorate (10; R = Me) with LAH or NaBH4 gave 3-methyl-2,3-dihydro-10bH-thiazolo[2,3-a]isoquinoline (7), 3-methyl-2,3,5,6-tetrahydro-10bH-thiazolo[2,3-a]isoquinoline (8) and a minor component of undetermined structure. 3-Bromomethyl-2,3-dihydrothiazolo[2,3-a]isoquinolinium perchiorate (12) obtained from (1) and bromine was hydrogenolysed with LAH to (7) and (8).Keywords
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