ChemInform Abstract The N-(alkoxycarbonyl)pyridinium chlorides (I), formed in situ from pyridine and alkyl chloroformates, react with allyltributyltin (II) to yield the 2-substituted 1,2-dihydropyridines (III) with a high regioselectivity, along with minor amounts of the 4-substituted 1,4-dihydropyridines (IV). The same α-regioselectivity is observed in the reaction of the m-substituted pyridines (V) with methyl chloroformate (VI) and (II) as outlined in the reaction scheme. No regioselectivity is found in the reaction of (Ia) with methallyl-and crotyltributyltin (IX), producing the compounds (X) and (XI). Further reactions are describted in the original paper.
Highly Regioselective -Allylation of TV-(Alkoxycarbonyl)pyridinium Salts by means of Allyltin Reagents Summary: TV-(Alkoxycarbonyl)pyridinium salts are regioselectively allylated in the «-positions by means of allyltributyltin to give a-allyl-l,2-dihydropyridines in moderate to good yields.
Bei der Behandlung mit Allyltributylzinn (II) erhält man aus N‐Alkoxycarbonylpyridiniumsalzen wie (I) mit hoher α‐Regioselektivität (91 ‐ 95%) die entsprechenden α‐Allylderivate wie (III).
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