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Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines

✍ Scribed by Meng-Yang Chang; Ming-Fang Lee; Nien-Chia Lee; Yu-Ping Huang; Chung-Han Lin

Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 615 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.11.131

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✦ Synopsis

A novel method for the synthesis of 1,2,4-trisubstituted-or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF 3 -OEt 2 )-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol.

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