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Synthesis of Terpyridines: Simple Reactions-What Could Possibly Go Wrong?

ABSTRACT: The preparation of 24-functionalized 12,22:26,32-terpyridines (4'-functionalized 3,2:6',3''-terpyridines) by the reaction of three 4-alkoxybenzaldehydes with 3-acetylpyridine and ammonia was investigated; under identical reaction conditions, two (R = nC4H9, C2H5) gave the expected products whereas a third (R = nC3H7) gave only a cyclohexanol derivative derived from the condensation of three molecules of 3-acetylpyridine with two of 4-(n-propoxy)benzaldehyde. A comprehensive survey of ''unexpected'' products from reactions of ArCOCH3 derivatives with aromatic aldehydes is presented. Three different types of alternative product are identified.

SUBMITTER: Rocco D

PROVIDER: S-EPMC6539753 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Synthesis of Terpyridines: Simple Reactions-What Could Possibly Go Wrong?

Rocco Dalila D Housecroft Catherine E CE Constable Edwin C EC

Molecules (Basel, Switzerland) 20190509 9

The preparation of 24-functionalized 12,22:26,32-terpyridines (4'-functionalized 3,2:6',3''-terpyridines) by the reaction of three 4-alkoxybenzaldehydes with 3-acetylpyridine and ammonia was investigated; under identical reaction conditions, two (R = nC4H9, C2H5) gave the expected products whereas a third (R = nC3H7) gave only a cyclohexanol derivative de ...[more]

PMID: 31075948

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