ao7b00627_si_001.pdf (4.77 MB)
Base-Promoted Selective Synthesis of 2H‑Pyranones and Tetrahydronaphthalenes via Domino Reactions
journal contribution
posted on 2017-08-24, 08:13 authored by Solaimalai Thimmarayaperumal, Sivakumar ShanmugamA highly efficient domino protocol
has been developed for the synthesis
of 6-aryl-4-(methylthio/amine-1-yl)-2-oxo-2H-pyran-3-carbonitriles
and 4-aryl-2-(amine-1-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitriles
from simple and readily available α-aroylketene dithioacetals,
malononitrile, secondary amines, and cyclohexanone. This elegant domino
process involved consecutive addition–elimination, intramolecular
cyclization, and ring opening and closing sequences. Notably, in situ
generated 2-imino-4-(methylthio/amine-1-yl)-6-aryl-2H-pyran-3-carbonitrile plays multiple roles in the construction of
various novel polyaromatic hydrocarbons.
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amines6-intramoleculardomino processTetrahydronaphthaleneDomino Reactionsiminocyclizationrolenovel polyaromatic hydrocarbons2-synthesisBase-Promotedpyran -3-carbonitrilesequenceα- aroylketene dithioacetalsconstructionpyran -3-carbonitrilesPyranonemalononitrilecyclohexanonearyldomino protocolring openingSynthesi4-
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