Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 22, Pages 4941-4946Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905483
Keywords
annulation; enaminones; enaminothiones; sulfur ylides; zinc
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Funding
- National Basic Research Program of China (973 Program) [2015CB856600] Funding Source: Medline
- National Natural Science Foundation of China [21871253 and 21672209] Funding Source: Medline
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Concise construction of furan and thiophene units has played an important role in the synthesis of potentially bioactive compounds and functional materials. Herein, an efficient Lewis acid ZnCl2 catalyzed [4+1] annulation of alkylthio-substituted enaminones is reported, that is, alpha-oxo ketene N,S-acetals with sulfur ylides to afford 2-acyl-3-aminofuran derivatives. In a similar fashion, [4+1] annulation of the corresponding enaminothiones, that is, alpha-thioxo ketene N,S-acetals, with sulfur ylides efficiently proceeded to give multisubstituted 3-aminothiophenes. This method features wide substrate scopes as well as broad functional group tolerance, offering a concise route to highly functionalized furans and thiophenes.
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