Palladium-catalyzed double carbonylation-based diversity-oriented synthesis of 3,4-dihydroisoquinoline-1-carboxamides

Masui, Hisashi; Ishizawa, Natsumi; Fuse, Shinichiro; Takahashi, Takashi

doi:10.1016/j.tet.2015.05.102

Cited by 7 publications

(1 citation statement)

References 40 publications

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“…[21][22][23] Takahashi reported a palladium-catalyzed double carbonylation method, followed by intramolecular condensation, to prepare such imino-carboxamides. 24 Such derivatives have been produced via Ugi-type reactions, which have also been used to synthesize medicinally relevant heterocycles. However, the practical applications of this approach remain limited.…”

Section: Introductionmentioning

confidence: 99%

Silylacetate-promoted addition reaction of isocyanides to nitrones: effective synthesis of C(1)-carboxamide derivatives

Soeta,

Yao,

Sugiyama

et al. 2024

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Silylacetate-promoted addition reaction of isocyanides to nitrones: effective synthesis of C(1)-carboxamide derivatives

Soeta,

Yao,

Sugiyama

et al. 2024

Org. Biomol. Chem.

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Double Carbonylation Reactions: Overview and Recent Advances

Das

Bhanage

2020

Adv Synth Catal

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The compounds like amides, carbamates, oxamates, oxamides, α‐keto amides, diketones, esters, ureas, etc. find extensive applications in pharmaceuticals, agrochemicals and organic synthesis. The classical syntheses of these compounds often involve cumbersome routes involving toxic chemicals. The carbonylation reactions such as aminocarbonylation, alkoxycarbonylation, oxidative carbonylation and double carbonylation deliver as an efficient and attractive alternative to the conventional synthetic routes even at industrial scales. The catalytic single carbonylation reactions are extensively studied, however, catalytic double carbonylation reactions are not explored for several potential applications. This review covers literature on the use of different types of catalysts involving various metals like Pd, Cu, Fe, Co, Rh and Ni for double carbonylation reactions along with the chemistry of associated ligands. It also covers double carbonylation with different types of substrates with the discussion related to the mechanism of formation of mono‐ and di‐carbonylation products. The notable introduction of several CO‐surrogates and exploration of their efficiency have solved the problems related to the toxicity of CO. CO‐surrogates used for double carbonylation reactions are also discussed.magnified image

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ChemInform Abstract: Palladium‐Catalyzed Double Carbonylation‐Based Diversity‐Oriented Synthesis of 3,4‐Dihydroisoquinoline‐1‐carboxamides.

et al. 2015

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Palladium-Catalyzed Double Carbonylation-Based Diversity-Oriented Synthesis of 3,4-Dihydroisoquinoline-1-carboxamides. -A novel synthetic methodology for the generation of dihydroisoquinoline carboxamides and its analogues is developed. First, the initial palladium-catalyzed double carbonylation of an N-protected aryl iodide and an amine partner affords intermediate -keto carboxamides. Subsequent treatment with trifluoroacetic acid leads to deprotection and intramolecular imine formation to afford the isoquinoline products. Isoindole (VIII) and benzoazepine (XI) carboxamide derivatives are obtained under similar conditions. -(MASUI, H.; ISHIZAWA, N.; FUSE, S.; TAKAHASHI*, T.; Tetrahedron 71 (2015) 37, 6354-6360, http://dx.

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Palladium-catalyzed double carbonylation-based diversity-oriented synthesis of 3,4-dihydroisoquinoline-1-carboxamides

Cited by 7 publications

References 40 publications

Silylacetate-promoted addition reaction of isocyanides to nitrones: effective synthesis of C(1)-carboxamide derivatives

Silylacetate-promoted addition reaction of isocyanides to nitrones: effective synthesis of C(1)-carboxamide derivatives

Double Carbonylation Reactions: Overview and Recent Advances

ChemInform Abstract: Palladium‐Catalyzed Double Carbonylation‐Based Diversity‐Oriented Synthesis of 3,4‐Dihydroisoquinoline‐1‐carboxamides.

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