ZnCl2-Promoted One-Pot Three-Component Synthesis of Multisubstituted Thiazolo[4,5-b]pyridines and Thieno[2,3-b:4,5-b′]dipyridines

A ZnCl2‐promoted one‐pot synthesis of multisubstituted thiazolo[4,5‐b]pyridines and thieno[2,3‐b:4,5‐b′]dipyridines from mercaptonitrile salts, α‐bromo ketones and ketones has been developed. This approach involves a tandem SN2 alkylation/Thorpe–Ziegler cyclization/Friedländer reaction, which allows...

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Veröffentlicht in:European journal of organic chemistry 2015-01, Vol.2015 (3), p.631-637
Hauptverfasser: Luo, Laichun, Meng, Lanlan, Peng, Yangqiu, Xing, Yongning, Sun, Qi, Ge, Zemei, Li, Runtao
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Sprache:eng
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Zusammenfassung:A ZnCl2‐promoted one‐pot synthesis of multisubstituted thiazolo[4,5‐b]pyridines and thieno[2,3‐b:4,5‐b′]dipyridines from mercaptonitrile salts, α‐bromo ketones and ketones has been developed. This approach involves a tandem SN2 alkylation/Thorpe–Ziegler cyclization/Friedländer reaction, which allows the creation of two hetero rings and four new bonds in a single operation. The reaction proceeds smoothly under solvent‐free conditions to afford fused pyridines in moderate to good yields. A facile ZnCl2‐promoted one‐pot three‐component synthesis of thiazolo[4,5‐b]pyridines and thieno[2,3‐b:4,5‐b′]dipyridines is described. This approach involves a tandem SN2/Thorpe–Ziegler cyclization/Friedländer reaction to give fused pyridines in moderate to good yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403156