Gold(I)-Catalyzed 6-endo-Dig Hydrative Cyclization of an Alkyne-Tethered Ynamide: Access to 1,6-Dihydropyridin-2(3H)ones

Ghosh, Nayan ; Nayak, Sanatan ; Sahoo, Akhila K. (2013) Gold(I)-Catalyzed 6-endo-Dig Hydrative Cyclization of an Alkyne-Tethered Ynamide: Access to 1,6-Dihydropyridin-2(3H)ones Chemistry - A European Journal, 19 (29). pp. 9428-9433. ISSN 0947-6539

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Official URL: http://doi.org/10.1002/chem.201301599

Related URL: http://dx.doi.org/10.1002/chem.201301599

Abstract

Hydrate your chemistry! Hydrative cyclization of 5-yne-ynamides in the presence of Echavarren's catalyst and p-toluenesulphonic acid (PTSA)⋅H2O at room temperature affords an array of 1,6-dihydropyridin-2(3H)one derivatives. Isomerization, epoxidation, and hydrogenation of the double bond and insertion of an extended π-conjugate system into the pyridinone skeleton have been successfully accomplished (see scheme; Ts=tosyl).

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Deposited On:02 Aug 2021 15:01
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