Synthesis of benzofulvenes through chemoselective Sonogashira and Barluenga couplings of ortho ethynyl-N-tosylhydrazones and cycloisomerization

Aziz, Jessy; Brion, Jean‐Daniel; Alami, Mouâd; Hamzé, Abdallah

doi:10.1039/c5ra14459k

Cited by 9 publications

(5 citation statements)

References 24 publications

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Section: Pd-catalyzed Carbene Coupling Reactionsmentioning

confidence: 75%

“…Furthermore, they developed a one-pot, two-step protocol for the synthesis of benzofulvenes starting from N-tosylhydrazones 320 and aryl iodides, which involved a sequence of palladiumcatalyzed carbene coupling and 5-exo-dig cyclization (Scheme 57b). 195 In 2014, Valdeś and co-workers developed an autotandem reaction between cyclic N-tosylhydrazones 321 and aryl dibromides 322, producing a series of spirocyclic compounds including spirofluorenes, spirodibenzofluorenes, spiroacridines, and spiroanthracenes. 196 A carbene coupling reaction and a subsequent intramolecular Heck reaction accounts for these two independent C−C bond forming processes, in which the Subsequently, the same group expanded the substrate scope and found that acyclic N-tosylhydrazones were also competent carbene precursors under similar reaction conditions.…”

Section: Cascade Process Of the Coupling Productsmentioning

confidence: 99%

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Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

2017

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Transition-metal-catalyzed cross-coupling reactions have been well-established as indispensable tools in modern organic synthesis. One of the major research goals in cross-coupling area is expanding the scope of the coupling partners. In the past decade, diazo compounds (or their precursors N-tosylhydrazones) have emerged as nucleophilic cross-coupling partners in C-C single bond or C═C double bond formations in transition-metal-catalyzed reactions. This type of coupling reaction involves the following general steps. First, the organometallic species is generated by various processes, including oxidative addition, transmetalation, cyclization, C-C bond cleavage, and C-H bond activation. Subsequently, the organometallic species reacts with the diazo substrate to generate metal carbene intermediate, which undergoes rapid migratory insertion to form a C-C bond. The new organometallic species generated from migratory insertion may undergo various transformations. This type of carbene-based coupling has proven to be general: various transition metals including Pd, Cu, Rh, Ni, Co, and Ir are effective catalysts; the scope of the reaction has also been extended to substrates other than diazo compounds; and various cascade processes have also been devised based on the carbene migratory insertion. This review will summarize the achievements made in this field since 2001.

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Section: Pd-catalyzed Carbene Coupling Reactionsmentioning

confidence: 75%

Section: Cascade Process Of the Coupling Productsmentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

2017

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“…231,232 In contrast to the Mizoroki-Heck cross-coupling reaction, the Barluenga cross-coupling does not require an alkene as a coupling partner, and produces a geminal alkene rather than a trans-alkene. Due to its advantageous functional group tolerance, this cross-coupling reaction has vast potential in synthetic chemistry, and proven applications in cancer treatments, 233 natural product synthesis, 234,235 and polymer synthesis. 236 Based on the fact that N -tosylhydrazones exhibit nucleophilic behaviour, in combination with previous palladium studies, Barluenga and coworkers 227 proposed the mechanism to begin with oxidative addition of the organic halide to the active palladium(0) complex (Figure 5.1).…”

Section: Introductionmentioning

confidence: 99%

A mechanistic investigation of the Pd-catalyzed cross-coupling betweenN-tosylhydrazones and aryl halides

2021

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“…Compounds 4d – e containing an alkyne function in the meta -position of iso CA-4 were obtained by using standard Sonogashira coupling of intermediate 3b with the corresponding alkynes in excellent yield . Treatment of ester 4d – e with hydroxylamine gave the desired hydroxamic acid derivatives 5d – e .…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Tubulin and Histone Deacetylase Inhibitor Based on iso-Combretastatin A-4

et al. 2018

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Designing multitarget drugs have raised considerable interest due to their advantages in the treatment of complex diseases such as cancer. Their design constitutes a challenge in antitumor drug discovery. The present study reports a dual inhibition of tubulin polymerization and HDAC activity. On the basis of 1,1-diarylethylenes ( isoCA-4) and belinostat, a series of hybrid molecules was successfully designed and synthesized. In particular compounds, 5f and 5h were proven to be potent inhibitors of both tubulin polymerization and HDAC8 leading to excellent antiproliferative activity.

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Synthesis of benzofulvenes through chemoselective Sonogashira and Barluenga couplings of ortho ethynyl-N-tosylhydrazones and cycloisomerization

Cited by 9 publications

References 24 publications

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

A mechanistic investigation of the Pd-catalyzed cross-coupling betweenN-tosylhydrazones and aryl halides

Design and Synthesis of Tubulin and Histone Deacetylase Inhibitor Based on iso-Combretastatin A-4

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