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Synthesis of Multisubstituted Dihydroquinoxaline Derivatives by Tandem N ‐Alkylation and Addition Reactions of 3‐Oxoquinoxaline‐2‐carboxylates
Author(s) -
Miyamaru Satoru,
Umezu Kazuto,
Ito Akinori,
Shimizu Makoto
Publication year - 2015
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.201500225
Subject(s) - chemistry , umpolung , alkylation , ring closing metathesis , tandem , metathesis , tricyclic , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , polymer , materials science , composite material , nucleophile , polymerization
This report describes a one‐pot synthesis of multisubstituted dihydroquinoxalin‐2‐ones using an umpolung N ‐alkylation followed by oxidation and C ‐alkylation reactions. Moreover, the synthesis of tricyclic compounds containing a dihydroquinoxaline skeleton was carried out by ring closing metathesis (RCM) of the resulting N , C ‐bis‐addition products containing olefins.