Efficient and rapid synthesis of N-substituted isoquinolin-1-ones under mild conditions: Facile access to doryanine derivatives

Takwale, Akshay D.; Jeon, Yeong Uk; Lee, Dong Hoon; Kim, Hyun Jin; Hwang, Jong Yeon

doi:10.1016/j.tetlet.2019.03.073

Cited by 8 publications

(3 citation statements)

References 23 publications

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“…Using trifluoroacetic acid (TFA) as a solvent, the intramolecular cyclization occurs to form isoquinolone ring with t-butyl group removed under the strong acidic conditions and microwave irradiation. A similar procedure was reported under mild conditions promoted by HCl in dioxane to give N-substituted 3,4-unsubstituted isoquinolones (Scheme 32 (b)) [117].…”

Section: Isoquinolone Syntheses Via Intramolecular Annulation Reactionsmentioning

confidence: 85%

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 Intramolecular Annulation Reactionsmentioning

confidence: 85%

Isoquinolone Syntheses by Annulation Protocols

Hua

2021

Catalysts

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“…Moreover, these heterocycles can be used as 5-HT3 antagonists [9], rho kinase inhibitors [10], thymidylate synthetase inhibitors [11], PARP-1 inhibitors [12], melatonin MT 1 and MT 2 receptor agonist [13], and fascin-targeted antimetastatic agents [14]. Fittingly, the development of efficient strategies for their construction and peripheral functionalization represents still an active research area aimed to achieve structural diversity [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

Nori¹,

Arcadi²,

Carlone³

et al. 2020

Beilstein J. Org. Chem.

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Cascade cyclocarbopalladation of the readily available aryl/alkyl-substituted propargylic amides containing an aryl iodide moiety, followed by Suzuki–Miyaura coupling with arylboronic acids, allowed an efficient regio- and stereoselective synthesis of tetrasubstituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones. Moreover, cascade cyclocarbopalladation, followed by the reaction with 2-alkynyltrifluoroacetanilides, accomplished a double cyclization to afford challenging 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones bearing a 3-indolyl substituent through aminopalladation/reductive elimination.

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“…In previous reports of 3,4-unsubstituted isoquinolone syntheses, a major challenge was obtaining good product yields from ortho-substituted starting materials. 14,30,31,34 Excitingly, our new strategy was able to efficiently generate 5-and 8-substituted isoquinolones 3b and 3n in moderate to good yield (55 and 81%, respectively). Previous attempts at synthesizing 8-methoxyisoquinolones had failed, 14 making the successful synthesis of 3n noteworthy.…”

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confidence: 95%