Claisen Rearrangement of Hydroxynaphthoquinones: Selectivity toward Naphthofuran or α‐Xiloidone Using Copper Salts and Iodine

Júnior, Paulo Eliandro da Silva; Araujo, Natália Maria de; Emery, Flávio da Silva

doi:10.1002/jhet.2087

Cited by 10 publications

(1 citation statement)

References 17 publications

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“…The obtained FNQ derivative 1a with the particular nature of inhibiting IDO1 deserves a deeper investigation, but the present synthesis research toward the FNQ skeleton is limited. Though two groups have reported the synthesis of 1a , both of these methods had several disadvantages (Figure ). The first method (reported by Perez et al) needs to be stirred under nitrogen for 24 h using Cs 2 CO 3 , CsI, and CuI as mediate.…”

Section: Introductionmentioning

confidence: 99%

Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors

et al. 2018

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An efficient reaction utilizing propargyl carbonates through Claisen rearrangement to synthesize furanonaphthoquinones is described. The remarkable transformation exhibits excellent functional group tolerance, affording the target furanonaphthoquinones in moderate to good yields (41-85%) under mild reaction conditions. Scaled-up preparation of the model product can make this reaction a method of choice for synthesis of furanonaphthoquinone derivatives. The resulting furanonaphthoquinones were evaluated as potential indoleamine 2,3-dioxygenase inhibitors in vitro.

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Section: Introductionmentioning

confidence: 99%

Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors

et al. 2018

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Molecular Rearrangement

Coxon¹

2019

Organic Reaction Mechanisms Series

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Microwave‐Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study

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Márquez‐Arce

et al. 2015

Chemistry A European J

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The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6π electrocyclization, and an aromatization reaction.

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Claisen Rearrangement of Hydroxynaphthoquinones: Selectivity toward Naphthofuran or α‐Xiloidone Using Copper Salts and Iodine

Abstract: α‐xiloidone is an interesting chromene that are structurally related to lapachones; in this work, we selectively synthesized α‐xiloidone from the reaction of lawsone 1 with 3,3‐chloro‐3‐methylbut‐1‐yne under copper/I2 catalysis via propargyl Claisen rearrangement.

Cited by 10 publications

References 17 publications

Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors

Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors

Molecular Rearrangement

Microwave‐Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study

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