NaOH-promoted reaction of 1,1-dihaloalkenes and 1<i>H</i>-azoles: synthesis of dihetaryl substituted alkenes

Zhang, Chen; Shi, Yulong; Zhang, Li-Yu; Yuan, Dong-Peng; Ban, Meng-Tao; Zheng, Jiangxia; Liu, Deng-Hui; Guo, Shun-Na; Cui, Dongmei

doi:10.1039/c8nj02756k

Cited by 6 publications

(4 citation statements)

References 38 publications

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“…Interestingly, an alternative route to these α-ketoamide products from N -alkynyl azoles was reported by Hwang in 2017 [76]. This method employs copper catalyst and irradiation with blue LEDs in the presence of 1 atm of O 2 (Scheme 43).…”

Section: Reactions Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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Section: Reactions Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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“…It is still desirable to develop mild but effective methods, which allow the construction of the C–X bond with high functional group tolerance. The Ullmann reaction is a traditional method using aryl halides and nucleophiles under transition metal catalysis [ 9 , 10 ]. Nevertheless, owing to its harsh reaction conditions, it is not applicable in certain cases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers

et al. 2023

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Novel 13α-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan–Lam couplings of arylboronic acids with 13α-estrone as a nucleophilic partner were carried out under copper catalysis. The antiproliferative activities of the newly synthesized diaryl ethers against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231, HeLa, SiHa) were investigated by means of MTT assays. The quinoline derivative displayed substantial antiproliferative activity against MCF-7 and HeLa cell lines with low micromolar IC50 values. Disturbance of tubulin polymerization has been confirmed by microplate-based photometric assay. Computational calculations reveal significant interactions of the quinoline derivative with the taxoid binding site of tubulin.

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“…Robert et al., reported the nitrogen atom of indoles can be functionalized with ynamides through base catalysis [Scheme 1 equation v] [22] . Cui and their research gruop reported that N ‐alkynyl pyrazoles reacted with pyrazoles in the presence of base to give mixture of alpha and beta substituted dipyrazolyl derivatives [Scheme 1 equation vi] [23] . Exploration of ynamide reactivity is emerging, [24] and different methods were established to obtain various heterocyclic and application oriented molecules [25] .…”

Section: Introductionmentioning

confidence: 99%

“…[22] Cui and their research gruop reported that N-alkynyl pyrazoles reacted with pyrazoles in the presence of base to give mixture of alpha and beta substituted dipyrazolyl derivatives [Scheme 1 equation vi]. [23] Exploration of ynamide reactivity is emerging, [24] and different methods were established to obtain various heterocyclic and application oriented molecules. [25] However, less attention has been paid on selectively tuning the reactivity of ynamides.…”

Section: Introductionmentioning

confidence: 99%