Structure and Mechanism Revision of a Catalyzed Cyclization of Benzaldehyde Bearing Alkyne-Nitrile

Pt­(II)-catalyzed carbocyclization of benzaldehyde containing a keto-nitrile functionality resulted in the formation, respectively, of isochromenes and spiro-lactones instead of fused lactams and spiro-lactams as was previously reported. The reaction mechanism was proposed, and the products were ide...

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Bibliographic Details
Published in:Organic letters 2017-09, Vol.19 (18), p.4742-4745
Main Authors: Šafář, Peter, Marchalín, Štefan, Šoral, Michal, Moncol, Ján, Daïch, Adam
Format: Article
Language:English
Subjects:
Chemical Sciences
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Summary:Pt­(II)-catalyzed carbocyclization of benzaldehyde containing a keto-nitrile functionality resulted in the formation, respectively, of isochromenes and spiro-lactones instead of fused lactams and spiro-lactams as was previously reported. The reaction mechanism was proposed, and the products were identified by multidimensional NMR, IR, and X-ray analysis. The structure of these new products was also confirmed by their synthesis in an unambiguous manner using practical and short approaches.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01881