Premium
Expedited Synthesis of Matrine Analogues through an Oxidative Cascade Addition/Double‐Cyclization Radical Process
Author(s) -
OlguínUribe Simón,
Mijangos Marco V.,
AmadorSánchez Yoarhy A.,
SánchezCarmona Miguel A.,
Miranda Luis D.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700208
Subject(s) - chemistry , xanthate , intramolecular force , matrine , tandem , radical cyclization , stereochemistry , indole alkaloid , intermolecular force , indole test , cascade reaction , double bond , derivative (finance) , cascade , combinatorial chemistry , molecule , organic chemistry , materials science , chromatography , financial economics , economics , composite material , catalysis
The addition of a nicotinate–xanthate derivative to N ‐allylindoles and N ‐allylpyrroles resulted in polycyclic heterocycle‐fused pyridonaphthyridines through a tandem radical intermolecular/intramolecular oxidative addition reaction sequence that created three new C–C bonds and two new rings in a single event. Such polyheterocycles showcase the matrine alkaloid framework and are similar to indole–monoterpenoid natural products.