Abstract
Reactions of several nitrogen heterocycles with sodium naphthalenide in aprotic solvents were investigated. The reactions were quenched with an aqueous buffer. Quinoline reacted by the single-electron transfer pathway to give a ‘dimeric’ (3), a ‘trimeric’ product (4) and 4-quinolone. 4-Quinazolinone afforded a single ‘dimeric’ product (9). Reaction of isoquinoline in monoglyme gave three ‘dimeric’ products and 4-hydroxy isoquinoline. N-Methyl oxindole gave a ‘dimeric’ and two ‘trimeric’ products. The structure of the products were established by spectroscopical techniques including two-dimensional NMR studies.
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