Synthesis of Triazolyl-Substituted Quinolizidine Imides

Autor:	Yen-Hao Hsu, Chang-Lin Lu, Shang‐Shing P. Chou
Rok vydání:	2012
Předmět:	chemistry.chemical_compound Quinolizidine chemistry Bicyclic molecule Click chemistry Triazole Organic chemistry General Chemistry Azide Metathesis Quinolizidines Sulfone
Zdroj:	Journal of the Chinese Chemical Society. 59:365-372
ISSN:	0009-4536
DOI:	10.1002/jccs.201100610
Popis:	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 Bu3SnH/AIBN, N-allylation and ring-closing metathesis (RCM) reaction then provided the bicyclic imides 21a-b.
Databáze:	OpenAIRE
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