Abstract
1-Methylthio-3-lithioisoquinoline 5a is readily generated from 1-methylthio-3bromoisoquinoline 5b and n-butyllithium in THF solution at – 78 oC. This lithium derivative was reacted with sundry electrophilic reagents to give various 1-methylthio-3-substitued isoquinolines 12. Two of the latter compounds ( 12b, R = Me) and 12f (R = CO2Me) were desulfurized to the corresponding 3-substituted isoquinolines 16a and 16b. Lithio species 5a is thus formally equivalent to the hypothetical 3-lithioisoquinoline 3a.
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