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First total synthesis of the 2,7-naphthyridine alkaloid neozeylanicine and unexpected formation of isoquinolines from ethoxyvinyl pyridines

✍ Scribed by Bracher, Franz ;Mink, Kathrin

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 310 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950490

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✦ Synopsis

Neozeylanicine I Alkaloid I 2,7-Naphthyridine I Isoquinolines 1 Electrocyclic reactions

The 2,?-naphthyridine alkaloid neozeylanicine (6) was prepared starting from 3-bromo-4-picoline (1) by side-chain methoxycarbonylation, Pd-catalyzed ring acetylation and onepot ring anellation in 32% overall yield. Condensation of the intermediate pyridyl enol ether 3 with dimethylformamide diethyl acetal to the enamine ? was followed by spontaneous electrocyclization to give the isoquinoline 8. On treatment with acid or base 3 was cyclized to the 6(2H)-isoquinolinone 10.

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