A one-pot construction of acridones by rhodium catalyzed reaction of N -phenyl-2-(1-sulfonyl-1 H -1,2,3-triazol-4-yl)aniline

Xu, Hua‐Dong; Pan, Ying-Peng; Ren, Xin-Tao; Zhang, Ping; Shen, Mei‐Hua

doi:10.1016/j.tetlet.2015.10.059

Cited by 13 publications

(6 citation statements)

References 35 publications

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“…N-methyl acridone derivatives [50]. The triazole intermediate was converted to acridone by rhodium catalysis via a single cycloaddition.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, the substrate 4l' with an intense electron-donor group diethyl amine also underwent a single cycloaddition reaction to give xanthone 7l' in 80% yield. Shen et al reported a similar process for the synthesis of N-methyl acridone derivatives [50]. The triazole intermediate was converted to acridone by rhodium catalysis via a single cycloaddition.…”

Section: Resultsmentioning

confidence: 99%

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Rhodium (II)-Catalyzed Synthesis of Tetracyclic 3,4-Fused Indoles and Dihydroindoles

et al. 2020

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“…N-methyl acridone derivatives [50]. The triazole intermediate was converted to acridone by rhodium catalysis via a single cycloaddition.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Rhodium (II)-Catalyzed Synthesis of Tetracyclic 3,4-Fused Indoles and Dihydroindoles

et al. 2020

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“…Subsequently, the same group also reported the synthesis of substituted 3-methylene-2,3-dihydrobenzofurans and 3-methylbenzofurans from 4-(aryloxymethyl)- N -tosyl-1 H -1,2,3-triazoles through insertion of the Rh carbenoid intermediate into the C–H bond . Similarly, Xu and Shen synthesized acridones from N -aryl-2-( N -sulfonyl-1,2,3-triazol-4-yl)anilines through a cascade reaction involving C–H insertion of the rhodium carbene into the N -aryl ring followed by oxidative cleavage …”

Section: Denitrogenative Transformations Of Triazolesmentioning

confidence: 99%

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

2022

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Readily accessible and shelf-stable 1,2,3-triazole and its analogues such as pyridotriazole, triazoloindole, benzotriazole, and thiadiazole exist in equilibrium with their ring-opened isomers, viz., diazo compounds. These ring-opened isomers could be trapped by various metal catalysts (e.g., Rh, Pd, Cu, Co, Ag, etc.) to generate the corresponding metal carbenoids with extrusion of nitrogen. As a consequence, these unique N-heterocycles facilitate access to a realm of N-containing complex structural motifs of biological importance through denitrogenative transformations such as transannulations, insertions, ylide formation, and rearrangements by trapping of the metal carbenoids with a diverse range of coupling partners (e.g., alkenes, alkynes, nitriles, carbo/heterocycles, X–H/C–X bonds, etc.). Hence, suitably substituted triazole derivatives have emerged as efficient surrogates of diazo compounds for the generation of reactive metal carbenoids during the past decades. In this comprehensive review, we aim to discuss in detail the remarkable advancement in their synthesis and synthetic applications.

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“…On the basis of these results, we conceived that the Rh-catalyzed denitrogenative cyclization of aryl triazoles would produce benzofulvene. To date, there have been reported Rh-catalyzed denitrogenative cyclization methods using a number of aryl triazoles including 4-(3-arylpropyl)-1-tosyl-1,2,3-triazole, 4-(aryloxymethyl)-1-tosyl-1,2,3-triazole, 4-( N -aryl- N -sulfonylaminomethyl)-1-tosyl-1,2,3-triazole, 4-( N -aryl- N -alkylaminomethyl)-1-tosyl-1,2,3-triazole, N -sulfonyl-4-biaryl-1-tosyl-1,2,3-triazole, and N -phenyl-2-(1-sulfonyl-1 H -1,2,3-triazole-4-yl)aniline for the synthesis of N -heterocyclic and carbocyclic compounds (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzofulvenes through Rhodium-Catalyzed Transannulation of Enynyl Triazoles

et al. 2016

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Rhodium-catalyzed denitrogenative cyclization of (E)-ethyl 2-(1-alkyl and arylsulfonyl-1H-1,2,3-triazol-4-yl)-3-aryl acrylate generated from (E)-ethyl 2-benzylidenebut-3-ynoates and N-sulfonyl azides in the presence of a copper catalyst was developed for the synthesis of a large number of functionalized benzofulvenes. Moreover, the synthesis of benzofulvenes was demonstrated as a one-pot method through tandem copper-catalyzed [3 + 2] cycloaddition and rhodium-catalyzed denitrogenative cyclization from (E)-ethyl 2-benzylidenebut-3-ynoates and N-sulfonyl azides.

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A one-pot construction of acridones by rhodium catalyzed reaction of N -phenyl-2-(1-sulfonyl-1 H -1,2,3-triazol-4-yl)aniline

Cited by 13 publications

References 35 publications

Rhodium (II)-Catalyzed Synthesis of Tetracyclic 3,4-Fused Indoles and Dihydroindoles

Rhodium (II)-Catalyzed Synthesis of Tetracyclic 3,4-Fused Indoles and Dihydroindoles

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

Synthesis of Benzofulvenes through Rhodium-Catalyzed Transannulation of Enynyl Triazoles

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