2013
DOI: 10.1039/c3cc43418d
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Synthesis of (spiro)cyclopentapyridinones via Csp3–H functionalization: a post-Ugi gold-catalyzed regioselective tandem cyclization

Abstract: A gold-catalyzed regioselective tandem cyclization of N-propynylbutynamide via Csp(3)-H functionalization has been described, providing a distinctive methodology for the architecture of cyclopentapyridinones as well as spirocyclopentapyridinones.

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Cited by 98 publications
(33 citation statements)
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“…63aed,f Van der Eycken utilized this methodology to synthesize cyclopentapyridinones, 64 while Ohno reported the synthesis of bi-and tricyclic pyrroles from N-propargyl ynamides under similar conditions. 65 Hashmi also reported the synthesis of benzothiophenes and benzofurans using similar chemistry, albeit via a different mechanism.…”
Section: Metal Vinylidenesmentioning
confidence: 99%
“…63aed,f Van der Eycken utilized this methodology to synthesize cyclopentapyridinones, 64 while Ohno reported the synthesis of bi-and tricyclic pyrroles from N-propargyl ynamides under similar conditions. 65 Hashmi also reported the synthesis of benzothiophenes and benzofurans using similar chemistry, albeit via a different mechanism.…”
Section: Metal Vinylidenesmentioning
confidence: 99%
“…4 In addition to these cyclizations of 1,5-diynes, a recent study reports the cyclization of the 1,6-diyne product of a Ugi four-component reaction by dual gold catalysis. 5 The mechanistic insights gained from these reactions quickly led to the preparation of a pre-catalyst, TDAC (Traceless Dual Activation Catalyst), which delivers the necessary two gold moieties in the needed σ-and π-coordinated fashion (Scheme 2). 6 A similar binding picture has been found for both mixed coinage metal σ,π-complexes and for dicopper complexes.…”
Section: Introductionmentioning
confidence: 99%
“…[7] In 2012, Zhang's group [8] and our group [9] independently described a new reactivity pattern of gold catalysts, in which two gold centres synchronously activate a diyne system (dual activation). [10] Herein, one gold center acts as p Lewis acidic compound activating one of the alkynes, whereas the other gold center forms a gold-acetylide, which then reacts as a nucleophile through the C a or C b atom (Scheme 2). Initially, the 5-endo cyclization pathway via the C b atom of the gold-acetylide was experimentally observed generating a gold-vinylidene species, which undergoes CÀH activation of nonactivated aliphatic [8, 9b] and aromatic [9a,c] CÀH bonds, as well as intermolecular CÀH bond activation processes (Scheme 2 a).…”
Section: Introductionmentioning
confidence: 99%