Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives

Sakai, Norio; Hori, Hiroaki; Yoshida, Yoshitoku; Konakahara, Takeo; Ogiwara, Yohei

doi:10.1016/j.tet.2015.05.068

Cited by 14 publications

(4 citation statements)

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“…To study one example of hemiaminal formation with the equilibrium shifted to the right, we chose methyl glyoxylate (methyl glyoxalate, methyl 2-oxoacetate, 7 ), where the presence of an EWG linked to the carbonyl may relatively stabilize the corresponding hemiaminal, HA-7a . Within each level of theory (see Table , first equilibrium), the use of smaller or larger basis sets almost did not affect the calculated reaction energies (as mentioned for other cases in which the differences in electronic delocalization of the molecules involved in the equilibria are not important).…”

Section: Resultsmentioning

confidence: 99%

Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data

et al. 2015

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While B3LYP, M06-2X, and MP2 calculations predict the ΔG° values for exchange equilibria between enamines and ketones with similar acceptable accuracy, the M06-2X/6-311+G(d,p) and MP2/6-311+G(d,p) methods are required for enamine formation reactions (for example, for enamine 5a, arising from 3-methylbutanal and pyrrolidine). Stronger disagreement was observed when calculated energies of hemiaminals (N,O-acetals) and aminals (N,N-acetals) were compared with experimental equilibrium constants, which are reported here for the first time. Although it is known that the B3LYP method does not provide a good description of the London dispersion forces, while M06-2X and MP2 may overestimate them, it is shown here how large the gaps are and that at least single-point calculations at the CCSD(T)/6-31+G(d) level should be used for these reaction intermediates; CCSD(T)/6-31+G(d) and CCSD(T)/6-311+G(d,p) calculations afford ΔG° values in some cases quite close to MP2/6-311+G(d,p) while in others closer to M06-2X/6-311+G(d,p). The effect of solvents is similarly predicted by the SMD, CPCM, and IEFPCM approaches (with energy differences below 1 kcal/mol).

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Section: Resultsmentioning

confidence: 99%

Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data

et al. 2015

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“…An alternative synthesis of 1-(diarylmethyl)piperidines is reported using a copper(I)-catalysed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals [ 99 ]. All compounds are racemates apart from compound 25e and were obtained in moderate yields (23–93%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of 1-(Diarylmethyl)-1H-1,2,4-triazoles and 1-(Diarylmethyl)-1H-imidazoles as a Novel Class of Anti-Mitotic Agent for Activity in Breast Cancer

et al. 2021

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We report the synthesis and biochemical evaluation of compounds that are designed as hybrids of the microtubule targeting benzophenone phenstatin and the aromatase inhibitor letrozole. A preliminary screening in estrogen receptor (ER)-positive MCF-7 breast cancer cells identified 5-((2H-1,2,3-triazol-1-yl)(3,4,5-trimethoxyphenyl)methyl)-2-methoxyphenol 24 as a potent antiproliferative compound with an IC50 value of 52 nM in MCF-7 breast cancer cells (ER+/PR+) and 74 nM in triple-negative MDA-MB-231 breast cancer cells. The compounds demonstrated significant G2/M phase cell cycle arrest and induction of apoptosis in the MCF-7 cell line, inhibited tubulin polymerisation, and were selective for cancer cells when evaluated in non-tumorigenic MCF-10A breast cells. The immunofluorescence staining of MCF-7 cells confirmed that the compounds targeted tubulin and induced multinucleation, which is a recognised sign of mitotic catastrophe. Computational docking studies of compounds 19e, 21l, and 24 in the colchicine binding site of tubulin indicated potential binding conformations for the compounds. Compounds 19e and 21l were also shown to selectively inhibit aromatase. These compounds are promising candidates for development as antiproliferative, aromatase inhibitory, and microtubule-disrupting agents for breast cancer.

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“…Sakai et al in 2015 reported a coupling reaction of aryl boronic acids (1) with N,O-acetals (2) and N,N-aminals (3) with copper(I) as catalyst leading to the formation of α-aryl glycines (4) and diarylmethylamines (10) (Scheme ). The authors observed that this catalyst successfully activated both the C(sp 3 )-O bond of N,O-acetals as well as the C(sp 3 )-N bond of N,N-aminals, but in the absence of any coordinating substituent, the C(sp 3 )-O bond of the N,O-acetal particularly gets activated.…”

Section: Resultsmentioning

confidence: 99%

Benzhydryl Amines: Synthesis and Their Biological Perspective

Roy

Panda

2019

ACS Omega

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The current review describes the recent progress in the chemistry and biology of the benzhydryl amines where the central carbon atom is directly attached to the nitrogen atom of one ring and which have published in the last five years (2015–2019). Both metal and metal-free racemic and asymmetric synthetic approaches along with their activities as anti-leishmanial, antiviral, antibacterial, and anti-aromatase and other miscellaneous properties are discussed.

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Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives

Cited by 14 publications

References 68 publications

Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data

Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data

Synthesis and Biological Evaluation of 1-(Diarylmethyl)-1H-1,2,4-triazoles and 1-(Diarylmethyl)-1H-imidazoles as a Novel Class of Anti-Mitotic Agent for Activity in Breast Cancer

Benzhydryl Amines: Synthesis and Their Biological Perspective

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