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Synthesis of Triazolyl‐Substituted Quinolizidine Imides
Author(s) -
Chou ShangShing P.,
Lu ChangLin,
Hsu YenHao
Publication year - 2012
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201100610
Subject(s) - chemistry , quinolizidine , bicyclic molecule , azide , ring closing metathesis , salt metathesis reaction , triazole , click chemistry , combinatorial chemistry , sulfone , metathesis , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , polymerization , alkaloid , polymer
Some bicyclic imides and triazole compounds have separately shown biological activities. We now combine these two structural features into the synthesis of triazolyl‐substituted quinolizidine imides 21 . Dihydro‐2‐pyridone compound 15 , obtained previously from the aza‐Diels‐Alder reaction, was first oxidized to the sulfone 16 which was effectively converted to the azide 17 . Further click chemistry of compound 17 with terminal alkynes provided regiospecifically the 1,4‐disubstituted triazoles 18a‐c . Sequential detosylation with Bu 3 SnH/AIBN, N ‐allylation and ring‐closing metathesis (RCM) reaction then provided the bicyclic imides 21a‐b .
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