Ag(I)‐Catalyzed/Acid‐Mediated Cascade Cyclization of <i>ortho</i>‐Alkynylaryl‐1,3‐dicarbonyls to Access Arylnaphthalenelactones and Furanonaphthol Libraries via Aryl‐Disengagement

Laohapaisan, Pavitra; Lumyong, Kanyapat; Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Chatwichien, Jaruwan; Supantanapong, Nantamon; Ruchirawat, Somsak

doi:10.1002/asia.202101212

Cited by 5 publications

(2 citation statements)

References 32 publications

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“…Moreover, R7000 with a naphthofuran core serves as a candidate antiparasitic drug, and compound I showed significant anticancer activity against human cancer cell lines. As a consequence, great attention has been paid to develop efficient approaches for the construction of naphthofuran scaffolds. − Among them, metal-catalyzed reactions − and organocatalytic reactions are generally the most effective methods toward the synthesis of naphthofurans, which resulted in the rapid development of synthetic methods for naphthofurans.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic (Z/E)-Selective Synthesis of 3-Vinylnaphthofurans via a Formal (3 + 2) Cycloaddition

Lei

Yao

et al. 2023

J. Org. Chem.

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A formal (3 + 2) cycloaddition of 1,4-enediones with 2-naphthols was established under the catalysis of trifluoromethanesulfonic acid as an organocatalyst, leading to the efficient synthesis of structurally diverse 3-vinylnaphthofurans with high yields and excellent (Z/E)-selectivities (up to 96% yield, all >20:1 Z/E). This formal (3 + 2) cycloaddition involved a cascade reaction process, and the intramolecular hydrogen bond in the structure of 3-vinylnaphthofurans should play an important role in controlling the (Z/E)-selectivity of the newly formed vinyl group. Moreover, this class of 3-vinylnaphthofurans was discovered to have an axial chirality. This work provides an organocatalytic approach for constructing multi-substituted vinylnaphthofurans via a cascade reaction with excellent control of the (Z/E)-selectivity, which will serve as a useful strategy for synthesizing vinylnaphthofurans via in situ construction of the furan core and formation of the vinyl group.

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Section: Introductionmentioning

confidence: 99%

Organocatalytic (Z/E)-Selective Synthesis of 3-Vinylnaphthofurans via a Formal (3 + 2) Cycloaddition

Lei

Yao

et al. 2023

J. Org. Chem.

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“…Among efficient ways leading to core structure [21,22], of special interest to us is the protocol of Ag(I) acid-catalyzed oxazole benz annulation for the synthesis of substituted naphthooxazole [23]. Although the silver catalyst was taken as the best activator for benz annulation of ortho-alkynylarylketones in previous methods [24,25], there is no report about detailed mechanistic study for this catalyzed Sonogashira coupling between orthoiodoarylketone and N-propargylamide.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of Ag(I) Acid-catalysed Cascade Benz Annulation of N-(3-(2-(4-Methoxybenzoyl)phenyl)prop-2-yn-1-yl)benzamide for Synthesis of Naphthooxazole

Lu¹,

Miao²,

Lan³

2023

Act Scie Pharma

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The mechanism is investigated for cascade benz annulation of phenyl)prop-2-yn-1-yl)benzamide catalyzed by Ag(I). The oxonium-ion generation and water nucleophilic addition induces ring opening hydroxylation, dual ketonization giving 1,5-diketone intermediate. Mediated by acid, the intramolecular cyclization, water elimination affords β-naphthol, from which the nucleophilic cyclization dehydration provides desired product naphthooxazole. The side reaction of acid-activated 5-exo-dig cyclization is accompanied by synergetic synchronous hydrolysis yielding indenone. The promotion of Ag(I) lies in the absolute energy and activation barrier decrease of oxonium-ion generation and water nucleophilic addition. The mediation of acid exists in intramolecular cyclization, nucleophilic cyclization dehydration and 5-exo-dig cyclization. The solvent influence of acid is smaller than Ag(I) from the reduction degree. These results are supported by Multiwfn analysis on FMO of specific TSs and MBO value of vital bonding, breaking.

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Synthesis of Naphtho[2,3-d]oxazoles via Ag(I) Acid-Mediated Oxazole-Benzannulation of ortho-Alkynylamidoarylketones

et al. 2022

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A cascade oxazole-benzannulation for the synthesis of naphtho [2,3-d]oxazoles has been developed employing orthoalkynylamidoarylketones as substrates. This procedure provides the advantage of preparing a wide variety of substituents on naphtho[2,3-d]oxazole structures. In addition, o-alkynylamidoarylketones could be prepared from easily accessible and a wide variety of commercially available starting materials. Therefore, this method is a judicious choice of strategy to synthesize naphtho [2,3d]oxazoles with a great variety of substituents. In this work, 27 examples were demonstrated to provide the desired products in moderate to good yields.

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Ag(I)‐Catalyzed/Acid‐Mediated Cascade Cyclization of ortho‐Alkynylaryl‐1,3‐dicarbonyls to Access Arylnaphthalenelactones and Furanonaphthol Libraries via Aryl‐Disengagement

Cited by 5 publications

References 32 publications

Organocatalytic (Z/E)-Selective Synthesis of 3-Vinylnaphthofurans via a Formal (3 + 2) Cycloaddition

Organocatalytic (Z/E)-Selective Synthesis of 3-Vinylnaphthofurans via a Formal (3 + 2) Cycloaddition

Theoretical Investigation of Ag(I) Acid-catalysed Cascade Benz Annulation of N-(3-(2-(4-Methoxybenzoyl)phenyl)prop-2-yn-1-yl)benzamide for Synthesis of Naphthooxazole

Synthesis of Naphtho[2,3-d]oxazoles via Ag(I) Acid-Mediated Oxazole-Benzannulation of ortho-Alkynylamidoarylketones

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