Isoquinolone Synthesis via Zn(OTf)2-Catalyzed Aerobic Cyclocondensation of 2-(1-Alkynyl)-benzaldehydes with Arylamines

Khan, Sajjad Ahmad; Hua, Ruimao

doi:10.3390/catal10060683

Cited by 12 publications

(8 citation statements)

References 53 publications

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“…Cu(OAc) 2 -catalyzed cyclocondensation of ortho-(1-alkynyl)benzaldehydes with aniline gives 2,3-diphenylisoquinolone in 63% yield [99]. Zn(OTf) 2 also shows catalytic activity for the aerobic cyclocondensation of ortho-(1-alkynyl)benzaldehydes with arylamines to give N-arylated isoquinolones [100]. The proposed mechanism involves two well-known steps of nucleophilic addition of arylamines to aldehyde, and intramolecular hydroamination followed by oxidation reaction affording isoquinolone.…”

Section: Isoquinolone Syntheses Via [5 + 1] Intermolecular Annulation Between Ortho-(1-alkynyl)benzaldehyde and Primary Aminesmentioning

confidence: 99%

Isoquinolone Syntheses by Annulation Protocols

Hua

2021

Catalysts

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Isoquinolones (isoquinolin-1(2H)-ones) are one of the important nitrogen-heterocyclic compounds having versatile biological and physiological activities, and their synthetic methods have been recently developed greatly. This short review illustrates the significant advances in the construction of isoquinolone ring with atom- and step-economy, focusing on the intermolecular annulation protocols and intramolecular cyclization in the presence of a variety of catalyst systems. The syntheses of isoquinolone-fused rings are also included.

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Section: Isoquinolone Syntheses Via [5 + 1] Intermolecular Annulation Between Ortho-(1-alkynyl)benzaldehyde and Primary Aminesmentioning

confidence: 99%

Isoquinolone Syntheses by Annulation Protocols

Hua

2021

Catalysts

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“…In 2020, Khan and Hua [113] reported Zn(OTf) 2 ‐catalyzed isoquinolin‐1(2 H )‐ones 215 synthesis by reacting ortho ‐alkynylbenzaldehydes 213 with different arylamines 214 in the using K 2 CO 3 base under O 2 atmosphere (Scheme 73). Various EDGs and EWGs present on both the substrates 213 and 214 give the isoquinolin‐1(2 H )‐ones in high yields (up to 85%).…”

Section: Metal‐catalyzed Synthesis Of Isoquinolinesmentioning

confidence: 99%

Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

Maikhuri,

Rawat,

Rawat

2023

Adv Synth Catal

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The preservation of scarce rare earth metals, such as palladium, rhodium, iridium, and others, poses a significant challenge for humanity due to their limited availability. These rare earth metals might be replaced by earth‐abundant 3d‐transition metals such as cobalt, manganese, iron, nickel, copper, etc. Isoquinolines have acquired an important position in synthetic organic chemistry as well as medicinal chemistry. They manifest in a diverse range of natural and synthetic molecules, serving as pivotal synthons for the synthesis of numerous bioactive compounds with notable medicinal significance. Numerous reports on the synthesis of isoquinoline derivatives via transition metal catalysis have been published worldwide. In this review, we summarize recent approaches for synthesizing various isoquinoline derivatives using 3d‐transition‐metal catalysts since 2020. The review has been divided into different 3d‐transition‐metal‐based catalysis. We expect that this review will bring a better overview of the present status of the significant progress made in the 3d‐transition‐metal‐based synthesis of isoquinolines and persuade more advancements and research in this area in the near future.

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“…In recent years, we have been interested in the applications of ortho -alkynyl aromatic aldehydes/ketones [ 13 ] and functionalized benzamides [ 14 , 15 ] in the synthesis of hetero-/carbo-cyclic compounds. Therefore, in continuation of our interests in development of synthetic methods for the synthesis of nitrogen-heterocyclic compounds via alkyne annulations [ 16 , 17 , 18 ], we herein describe a CuI/Pd(OAc) 2 -catalyzed formation of 11-aryl-6 H -isoindolo-[2,1- a ]-indol-6-ones bearing different functional group(s) from ortho -(1-arylethynyl)- N -arylbenzamides by the stepwise hydroamidation of the alkynyl group [ 19 ], and C-H dehydrogenative coupling reaction [ 20 ] with the use of O 2 as the oxidant ( Scheme 1 , Equation (3)).…”

Section: Introductionmentioning

confidence: 99%

Cu(I)/Pd(II)-Catalyzed Intramolecular Hydroamidation and C-H Dehydrogenative Coupling of ortho-Alkynyl-N-arylbenzamides for Access to Isoindolo[2,1-a]Indol-6-Ones

Bao-xin

Hua

2022

Molecules

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An efficient, atom-economic and one-pot synthesis of isoindolo[2,1-a]indol-6-ones via CuI/Pd(OAc)2-catalyzed intramolecular hydroamidation of alkynyl group, and C-H dehydrogenative coupling of ortho-alkynyl-N-arylbenzamides has been developed. This transformation occurs with the use of oxygen as the oxidant, and water is the only by-product. The reaction shows a high tolerance to a variety of functional groups, and affords isoindolo[2,1-a]indol-6-ones in good to high yields.

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Isoquinolone Synthesis via Zn(OTf)2-Catalyzed Aerobic Cyclocondensation of 2-(1-Alkynyl)-benzaldehydes with Arylamines

Cited by 12 publications

References 53 publications

Isoquinolone Syntheses by Annulation Protocols

Isoquinolone Syntheses by Annulation Protocols

Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

Cu(I)/Pd(II)-Catalyzed Intramolecular Hydroamidation and C-H Dehydrogenative Coupling of ortho-Alkynyl-N-arylbenzamides for Access to Isoindolo[2,1-a]Indol-6-Ones

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