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Paper | Regular issue | Vol 83, No. 9, 2011, pp.1989-2000
Published online, 21st July, 2011
DOI: 10.3987/COM-11-12239
Synthetic Studies of Substituted Pyridine Aldehydes as Intermediates for the Synthesis of Toddaquinoline, Its Derivatives and Other Natural Products

Georgeta Serban,* Hitoshi Abe, and Yasuo Takeuchi

*Pharmaceutical Chemistry Department, Faculty of Medicine and Pharmacy, University of Oradea, Nicolae Jiga 29, Oradea 410028, Romania

Abstract

The synthesis of substituted 2-bromopyridine aldehydes as intermediates in our planned approach to toddaquinoline, its derivatives and other natural products is reported. The DMF-formylation method of pyridine ring, the Vilsmeier-Haack procedure and the bromination of pyridine ring respectively, were studied in order to synthesize the above mentioned compounds. The successful methods (DMF-formylation and bromination of pyridine ring) provided the 2-bromo-4-formyl-5-tosyloxypyridine Ib and 5-benzyloxy-2,4,6-tribromo- nicotinaldehyde Ia under relatively mild conditions and in good yields.