La(OTf)3‑Catalyzed [3+2] Cycloaddition Reactions for the Synthesis of Benzo[d]oxazoles/Benzofurans

The La­(OTf)3-catalyzed [3+2] cycloaddition reactions for the synthesis of benzo­[d]­oxazoles/benzofurans via quinones and 1,2-di-tert-butyl-3-(cyanimino)­diaziridine (1,3-di-tert-butyl-2-cyanoguanidine)/vinyl azides have been explored. A series of 5-hydroxybenzofuran-4-carboxylic acid derivatives a...

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Veröffentlicht in:Journal of organic chemistry 2024-03, Vol.89 (6), p.3809-3820
Hauptverfasser: Li, Zhanjun, Zhang, Yalin, Sun, Manman, Zhang, Ye, Lu, Zhaoxiang, Deng, Yupeng, Huang, Xianqiang, Shen, Guodong
Format: Artikel
Sprache:eng
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Zusammenfassung:The La­(OTf)3-catalyzed [3+2] cycloaddition reactions for the synthesis of benzo­[d]­oxazoles/benzofurans via quinones and 1,2-di-tert-butyl-3-(cyanimino)­diaziridine (1,3-di-tert-butyl-2-cyanoguanidine)/vinyl azides have been explored. A series of 5-hydroxybenzofuran-4-carboxylic acid derivatives and 5-hydroxybenzo­[d]­oxazole-4-carboxylic acid derivatives were conveniently obtained with high yields and good stereoselectivities, which could be used for further transformations to valuable compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02641