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Extra resources for Heterocyclic Chemistry
Example text
Etb L N H E~ N H Note that 0-Si bonds are stronger than N-C bonds Reactions These compounds undergo electrophilic substitution readily, but their chemistry is quite complex; for example, 2-and 4-pyridones, although weak bases (amide-like), protonate at oxygen. Some other electrophiles, particularly those which bond strongly to oxygen, also react at this site. 24). 25). 27). 28). When the sites adjacent to the nitrogen are blocked, however, attack occurs at C-4. The products are dihydropyridines.
17). This product is then reduced to the P-phenylethylamine, commonly by the action of lithium aluminium hydride. 18). Finally, aromatization is accomplished by heating the 3,4-dihydroisoquinoline over palladium on charcoal. 18 Alternatively, a P-methoxy-P-phenylethylaminecan be used to circumvent the oxidation step after the conventional Bischler-NaDerialski cyclization. Here, when treated with the phosphorus reagent the amide (R'= OMe) undergoes both cyclization and the elimination of methanol to give the isoquinoline (R = H) directly.
14). 16). 'B-qHh -yb-0cBr Br B- NH3 -B r- -BH N NH2 N N 3-Pyridyne N This occurs because 3-pyridyne (3,4-didehydropyridine) is formed by an ElcB process [elimination (first order) from the conjugate base]. 3-Pyridyne then adds ammonia; the addition is not regiospecific and two amino derivatives are formed. 16 +H2N N is the An alternative addition of NH; to 3-pyridyne, bv . , Drotonation as the second step. 28 Heterocyclic Chemistry 285 Lithiation ~~~ ~ Halogenopyridines can undergo metal-halogen exchange when treated with butyllithium.