Copper-catalyzed asymmetric 1,6-conjugate addition of <i>in situ</i> generated <i>para</i>-quinone methides with β-ketoesters

Wang, Yi-Feng; Wang, Chaojie; Feng, Qing-Zhou; Zhai, Jing-Jing; Qi, Suo-Suo; Zhong, Aiguo; Chu, Mingming; D, Xu

doi:10.1039/d2cc00146b

Cited by 56 publications

(13 citation statements)

References 37 publications

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“…Besides coordination chemistry, Schiff bases are strong candidates in analytical chemistry because of their significant applications in this field [ 4 ]. Moreover, the exploration of Imines in the field of medicinal chemistry has also been well recognized because of their potential as anticancer [ 5 ], anti-tubercular [ 6 ], analgesic and anti-inflammatory [ 7 ], antimicrobial [ 8 , 9 ], antioxidant [ 10 , 11 ], anthelmintic [ 12 ] and anticonvulsant medicines [ 13 , 14 , 15 , 16 , 17 ], etc. Imines derived from primary amines are basic in nature, while in acidic solution they readily convert in to iminium ions [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Imine-Carboxylic Acid Functionalized Compounds: Single Crystal, Hirshfeld Surface and Quantum Chemical Exploration

et al. 2023

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Two aminobenzoic acid based crystalline imines (HMBA and DHBA) were synthesized through a condensation reaction of 4-aminobenzoic acid and substituted benzaldehydes. Single-crystal X-ray diffraction was employed for the determination of structures of prepared Schiff bases. The stability of super molecular structures of both molecules was achieved by intramolecular H-bonding accompanied by strong, as well as comparatively weak, intermolecular attractive forces. The comparative analysis of the non-covalent forces in HMBA and DHBA was performed by Hirshfeld surface analysis and an interaction energy study between the molecular pairs. Along with the synthesis, quantum chemical calculations were also accomplished at M06/6-311G (d, p) functional of density functional theory (DFT). The frontier molecular orbitals (FMOs), molecular electrostatic potential (MEP), natural bond orbitals (NBOs), global reactivity parameters (GRPs) and natural population (NPA) analyses were also carried out. The findings of FMOs found that Egap for HMBA was examined to be smaller (3.477 eV) than that of DHBA (3.7933 eV), which indicated a greater charge transference rate in HMBA. Further, the NBO analysis showed the efficient intramolecular charge transfer (ICT), as studied by Hirshfeld surface analysis.

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Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Imine-Carboxylic Acid Functionalized Compounds: Single Crystal, Hirshfeld Surface and Quantum Chemical Exploration

et al. 2023

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“…α-Ketodithiocarbamates are valuable precursors for 2-dialkylamino-1,3-dithiolium-2-yl cations [ 21 , 22 , 23 ]. Usually, the acid-catalysed cyclocondensation of these substrates is the method employed for the synthesis of the desired 1,3-dithiolium cations.…”

Section: Resultsmentioning

confidence: 99%

An Improved Synthetic Method for Sensitive Iodine Containing Tricyclic Flavonoids

Birsa

Sarbu

2022

Molecules

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The synthesis of new iodine containing synthetic tricyclic flavonoids is reported. Due to the sensitivity of the precursors to the heat and acidic conditions required for the ring closure of the 1,3-dithiolium core, a new cyclization method has been developed. It consists in the treatment of the corresponding iodine-substituted 3-dithiocarbamic flavonoids with a 1:1 (v/v) mixture of glacial acetic acid–concentrated sulfuric acid at 40 °C. The synthesis of the iodine-substituted 3-dithiocarbamic flavonoids has also been tuned in terms of reaction conditions.

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“…Later, Yudin et al achieved the synthesis of boryliminocoumarin from borylketenimines [ 25 ], although these methods were limited to certain building blocks. On the other hand, the metal-catalyzed conjugate addition of diboranes remained a valuable tool for inserting boron into unsaturated molecular motifs [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. In recent years, copper-catalyzed conjugate addition reactions [ 32 ] of boron have emerged as a viable method to construct borylated heterocycles [ 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, the metal-catalyzed conjugate addition of diboranes remained a valuable tool for inserting boron into unsaturated molecular motifs [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. In recent years, copper-catalyzed conjugate addition reactions [ 32 ] of boron have emerged as a viable method to construct borylated heterocycles [ 33 , 34 ]. Among them, the dearomative borylation strategy of indoles [ 35 , 36 , 37 ], pyrroles [ 37 , 38 ], pyridines [ 39 ], and 4-quinolinols [ 40 ] have been efficiently utilized to construct borylated analogs of these biologically significant frameworks.…”

Section: Introductionmentioning

confidence: 99%

Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids

et al. 2023

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Dearomative borylation of coumarins and chromenes via conjugate addition represents a relatively unexplored and challenging task. To address this issue, herein, we report a new and general copper (I) catalyzed dearomative borylation process to synthesize boron-containing oxacycles. In this report, the borylation of coumarins, chromones, and chromenes comprising functional groups, such as esters, nitriles, carbonyls, and amides, has been achieved. In addition, the method generates different classes of potential boron-based retinoids, including the ones with oxadiazole and anthocyanin motifs. The borylated oxacycles can serve as suitable intermediates to generate a library of compounds.

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Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with β-ketoesters

Abstract: A Cu-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides (p-QMs) with β-ketoester has been developed to construct the ketoester skeleton bearing adjacent tertiary-quaternary carbon stereocenter in good yields...

Cited by 56 publications

References 37 publications

Efficient Synthesis of Imine-Carboxylic Acid Functionalized Compounds: Single Crystal, Hirshfeld Surface and Quantum Chemical Exploration

Efficient Synthesis of Imine-Carboxylic Acid Functionalized Compounds: Single Crystal, Hirshfeld Surface and Quantum Chemical Exploration

An Improved Synthetic Method for Sensitive Iodine Containing Tricyclic Flavonoids

Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids

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