112561-62-3Relevant articles and documents
First Total Synthesis of the 2,7-Naphthyridine Alkaloid Neozeylanicine and Unexpected Formation of Isoquinolines from Ethoxyvinyl Pyridines
Bracher, Franz,Mink, Kathrin
, p. 645 - 648 (2007/10/02)
The 2,7-naphthyridine alkaloid neozeylanicine (6) was prepared starting from 3-bromo-4-picoline (1) by side-chain methoxycarbonylation, Pd-catalyzed ring acetylation and one-pot ring annelation in 32percent overall yield.Condensation of the intermediate pyridyl enol ether 3 with dimethylformamide diethyl acetal to the enamine 7 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. - Key Words: Neozeylanicine / Alkaloid / 2,7-Naphthyridine / Isoquinolines / Electrocyclic reactions