Rh(<scp>iii</scp>)-catalyzed synthesis of tetracyclic isoquinolinium salts <i>via</i> C–H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol

Dang, Xinxin; He, Yanfang; Liu, Yingtian; Chen, Xuehong; Li, Junlong; Zhou, Xian Li; Jiang, Heng; Li, Jiahong

doi:10.1039/c8ra05443f

RSC Adv.

2018

DOI: 10.1039/c8ra05443f

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Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C–H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol

Xinxin Dang

Yanfang He

Yingtian Liu

et al.

Abstract: An efficient method to construct tetracyclic isoquinolinium salts via C–H activation and [4 + 2] annulation reactions in ethanol is described.

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Cited by 2 publications

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Synthesis of Azonia Aromatic Heterocycles Bearing 6–6–6–5–6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition and Oxidative Aromatization Reaction Sequence in One Pot

Saini,

Prajapati,

Basak

2023

J. Org. Chem.

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Cationic aza-heterocycle-fused compounds have gained wide applications in materials science, biological applications, and synthetic organic chemistry. In this report, synthesis of benzothiazolochromenopyridinium tetrafluoroborates, a novel molecular scaffold, bearing 6−6−6−5−6 pentacyclic core is described that proceeds via (i) piperidine-catalyzed Knoevenagel condensation between 2-propargyloxyarylaldehydes bearing internal alkynes and 2-benzothiazoleacetonitrile, (ii) intramolecular formal [4 + 2]-cycloaddition, and (iii) crucial molecular oxygenmediated oxidative aromatization reaction sequence in one pot. These quaternary pyridinium salts are obtained at ambient temperature in good to high yields.

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Synthesis of Azonia Aromatic Heterocycles Bearing 6–6–6–5–6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition and Oxidative Aromatization Reaction Sequence in One Pot

Saini,

Prajapati,

Basak

2023

J. Org. Chem.

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Hydrolysis of dihydroisoquinoline derivatives activated by sulfonyl or acyl chloride

et al. 2020

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A new, efficient, and mild strategy for hydrolysis of 3,4-dihydroisoquinoline imines activated by sulfonyl chloride or acyl chloride has been developed, by which method ketosulfonamides and ketoamides have been synthesized. This process tolerates broad scope with respect to both the sulfonyl chloride and acyl chloride with moderate to excellent yields. This protocol features a broad substrate scope for various kinds of 3,4-dihydroisoquinoline and mild reaction conditions without using strong acidic or basic condition. These features show that this user-friendly and simple system could be applied in the future to the synthesis of a broader range of amino benzophenones.

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Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C–H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol

Abstract: An efficient method to construct tetracyclic isoquinolinium salts via C–H activation and [4 + 2] annulation reactions in ethanol is described.

Cited by 2 publications

References 49 publications

Synthesis of Azonia Aromatic Heterocycles Bearing 6–6–6–5–6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition and Oxidative Aromatization Reaction Sequence in One Pot

Synthesis of Azonia Aromatic Heterocycles Bearing 6–6–6–5–6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition and Oxidative Aromatization Reaction Sequence in One Pot

Hydrolysis of dihydroisoquinoline derivatives activated by sulfonyl or acyl chloride

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