Fe(II)/Au(I) Relay Catalyzed Propargylisoxazole to Pyridine Isomerization: Access to 6-Halonicotinates.

Autor: Galenko AV; Saint Petersburg State University , Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034 Russia., Shakirova FM; Saint Petersburg State University , Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034 Russia., Galenko EE; Saint Petersburg State University , Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034 Russia., Novikov MS; Saint Petersburg State University , Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034 Russia., Khlebnikov AF; Saint Petersburg State University , Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034 Russia.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2017 May 19; Vol. 82 (10), pp. 5367-5379. Date of Electronic Publication: 2017 May 05.
DOI: 10.1021/acs.joc.7b00736
Abstrakt: An efficient synthesis of methyl nicotinates/6-halonicotinates by the domino isomerization of 4-propargyl/(3-halopropargyl)-5-methoxyisoxazoles under Fe(II)/Au(I) relay catalysis was developed. It was found that FeNTf 2 is an effective catalyst for first step of the domino isomerization, transformation of isoxazole to 2H-azirine, which is compatible with Ph 3 PAuNTf 2 , catalyzing the second step.
Databáze: MEDLINE
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