Organic Letters
Organic Letters
5 years ago

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

Structure and Mechanism Revision of a Catalyzed Cyclization of Benzaldehyde Bearing Alkyne-Nitrile
Adam Daïch, Ján Moncol, Peter Šafář, Michal Šoral, Štefan Marchalín
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01881

DOI: 10.1021/acs.orglett.7b01881

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