Reserpine Analogs; Phenethylamine Derivatives<sup>1</sup>

Lindner, A; Claassen, Vasti; Hendriksen, Th. W. J.; Kralt, T.

doi:10.1021/jm00338a002

Cited by 10 publications

(1 citation statement)

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“…Similarly, products SF14 – SF16 were obtained in 59–86% yields when 2-(1 H -indol-1-yl)anilines and alkynoic acids were subjected to the modified conditions. Notably, the indole-containing polycyclic frameworks, represented by compounds SF1 – SF16, are regarded as valuable N-heterocycles considering their ubiquitous presence in biologically active molecules [59,60,61,62,63]. Subsequently, 2-(1 H -pyrrol-2-yl)ethanamines, 2-(1 H -pyrrol-1-yl)ethanamines, 2-(thiophen-2-yl)ethanamines, and 2-(thiophen-3-yl)ethanamines were employed as amine nucleophiles.…”

Section: Resultsmentioning

confidence: 99%

Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Jia

Liu

et al. 2019

Molecules

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The present study describes an AuPPh3Cl/AgSbF6-catalyzed cascade reaction between amine nucleophiles and alkynoic acids in water. This process proceeds in high step economy with water as the sole coproduct, and leads to the generation of two rings, together with the formation of three new bonds in a single operation. This green cascade process exhibits valuable features such as low catalyst loading, good to excellent yields, high efficiency in bond formation, excellent selectivity, great tolerance of functional groups, and extraordinarily broad substrate scope. In addition, this is the first example of the generation of an indole/thiophene/pyrrole/pyridine/naphthalene/benzene-fused N-heterocycle library through gold catalysis in water from readily available materials. Notably, the discovery of antibacterial molecules from this library demonstrates its high quality and potential for the identification of active pharmaceutical ingredients.

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Section: Resultsmentioning

confidence: 99%

Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Jia

Liu

et al. 2019

Molecules

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Gold‐catalyzed Rapid Construction of Nitrogen‐containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

Jin

Jia

et al. 2019

Adv Synth Catal

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1,3-unsubstituted 2-(1H-indol-2-yl)ethanamines were employed for the first time to react with alkynoic acids (AAs) to achieve gold-catalyzed highly selective cascade reactions to furnish novel indole-fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/ pyridine-based nitrogen-containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine nucleophiles (ANs) and diverse AAs as the building blocks. This general protocol features excellent selectivity, extraordinarily broad substrate scope, readily available inputs, good to high yields, high bond-forming efficiency, and step economy, thus providing a facile and efficient access to a variety of valuable nitrogen-containing heterocycles. LRMS (ESI) m/z: 218 [M + H] + ; HRMS (ESI) m/z calculated for C 12 H 11 NO 3 + H + 218.0812, found: 218.0809. 2 3 4 5 6 7 8

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Reserpine analogues V: Optical antipodes of two methoxy‐β‐phenylethylaminoalkyl methoxybenzoates

Kralt

Haeck

Peperkamp

1966

Recl. Trav. Chim. Pays‐Bas

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Reserpine Analogs; Phenethylamine Derivatives¹

Cited by 10 publications

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Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Gold‐catalyzed Rapid Construction of Nitrogen‐containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

Reserpine analogues V: Optical antipodes of two methoxy‐β‐phenylethylaminoalkyl methoxybenzoates

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Reserpine Analogs; Phenethylamine Derivatives1

Cited by 10 publications

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Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Gold‐catalyzed Rapid Construction of Nitrogen‐containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

Reserpine analogues V: Optical antipodes of two methoxy‐β‐phenylethylaminoalkyl methoxybenzoates

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Reserpine Analogs; Phenethylamine Derivatives¹