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Published on: February 23, 2016
Synthesis of Terpyridines: Simple Reactions-What Could Possibly Go Wrong?
Dalila Rocco1, Catherine E Housecroft2, Edwin C Constable3
1University of Basel, Department of Chemistry, BPR 1096, Mattenstrasse 24a, CH-4058 Basel, Switzerland. dalila.rocco@unibas.ch.
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.
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