Study on products and reaction paths for synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine from phenol, aniline and formaldehyde

Zhang, Cheng-Xi; Deng, Yuyuan; Zhang, Yiyang; Yang, Po Chih; Gu, Yi

doi:10.1016/j.cclet.2014.12.005

Cited by 16 publications

(25 citation statements)

References 29 publications

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“…Benzoxazine was synthesized according to the literature [29]. First, 0.2 M aniline and 0.4 M formaldehyde were dissolved in toluene (50 mL), and the mixture was stirred at 40 • C for 1 h. Then, 0.2 M phenol was added into the above mixture and refluxed at 110 • C. After 6 h, the upper organic phase was transferred to a flask with one neck, and then distilled using rotary evaporators.…”

Section: Synthesis Of Aniline-phenol Benzoxazinementioning

confidence: 99%

Synthesis of Benzoxazine-Based N-Doped Mesoporous Carbons as High-Performance Electrode Materials

Zhang

Liu

2020

Applied Sciences

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In this work, nitrogen-doped carbon materials (NCMs) were prepared using aniline-phenol benzoxazine (BOZ) or aniline-cardanol benzoxazine as the carbon precursor and SBA-15 as the hard template. The effects of the carbonization temperature (700, 800, and 900 °C) and different nitrogen contents on the electrochemical properties of carbon materials were investigated. The samples synthesized using aniline-phenol benzoxazine as precursors and treated at 900 °C (NCM-900) exhibited an excellent electrochemical performance. The specific capacitance was 460 F/g at a current density of 0.25 A/g and the cycle stability was excellent (96.1% retention rate of the initial capacitance after 2000 cycles) in a 0.5 M H2SO4 electrolyte with a three-electrode system. Furthermore, NCM-900 also exhibited a high specific capacitance, comparable energy/power densities, and excellent cycling stability using a symmetrical electrode system. The characterization of the morphology and structure of the materials suggests it possessed an ordered mesoporous structure and a large specific surface area. NCM-900 could thus be considered a promising electrode material for supercapacitors.

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Section: Synthesis Of Aniline-phenol Benzoxazinementioning

confidence: 99%

Synthesis of Benzoxazine-Based N-Doped Mesoporous Carbons as High-Performance Electrode Materials

Zhang

Liu

2020

Applied Sciences

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“…32 On the other hand, the kinetics and details study of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine synthesis by Mannich reaction were investigated. 16 It was observed that, N-hydroxymethyl aniline (HMA) is considered the key intermediate. HMA then reacts with phenol to give second intermediate (3) which reacts with formaldehyde to form benzoxazines.…”

Section: Synthesis Of 34-dihydro-2h-13-benzoxazinesmentioning

confidence: 99%

“…So, this research observed that, the formation and the mechanism of benzoxazines synthesis beside the formation of byproducts well need further investigations. 16…”

Section: Synthesis Of 34-dihydro-2h-13-benzoxazinesmentioning

confidence: 99%

“…Interestingly, benzoxazin-4-onium perchlorate (15) reacts with dialdehyde methyl 3,5-diformyl-2,4-dihydroxybenzoate (16) in glacial acetic acid obtaining spiropyran of 1,3-benzoxazine series (5) through the formation of intermediate styryl salt (17). This intermediate has been isolated and then cyclized under the action of triethylamine in anhydrous diethyl ether to yield the compound (18) as shown in Scheme 22.…”

Section: 1 Reaction Of 4h-13-benzoxazin-4-onium Saltsmentioning

confidence: 99%

“…Subsequently, these problems need further efforts and studies. 10,16 Furthermore, benzoxazine nucleus not only is present in many pharmacologically active molecules, medicinally significant derivatives and natural products but also they have been used as intermediates for the synthesis of other heterocyclic scaffold of bioactive compounds. 17 Also, several of 1,3-benzoxazines ( Figure 3) show interesting biological and pharmaceutical properties.…”

Section: Introductionmentioning

confidence: 99%

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3,4-Dihydro-2H-1,3-benzoxazines and their oxo-derivatives - Chemistry and bioactivities

Eldin

2021

JSCS

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It must be stressed that the manuscript still has to be subjected to copyediting, typesetting, English grammar and syntax corrections, professional editing and authors' review of the galley proof before it is published in its final form. Please note that during these publishing processes, many errors may emerge which could affect the final content of the manuscript and all legal disclaimers applied according to the policies of the Journal.

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Ambient Preparation of Benzoxazine‐based Phenolic Resins Enables Long‐term Sustainable Photosynthesis of Hydrogen Peroxide

et al. 2023

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Rational design of polymer structures at the molecular level promotes the iteration of high-performance photocatalyst for sustainable photocatalytic hydrogen peroxide (H 2 O 2 ) production from oxygen and water, which also lays the basis for revealing the reaction mechanism. Here we report a benzoxazine-based maminophenol-formaldehyde resin (APFac) polymerized at ambient conditions, exhibiting superior H 2 O 2 yield and long-term stability to most polymeric photocatalysts. Benzoxazine structure was identified as the crucial photocatalytic active segment in APFac. Favorable adsorption of oxygen/intermediates on benzoxazine structure and commendable product selectivity accelerated the reaction kinetically in stepwise single-electron oxygen reduction reaction. The proposed benzoxazinebased phenolic resin provides the possibility of production in batches and industrial application, and sheds light on the de novo design and analysis of metal-free polymeric photocatalysts.

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Study on products and reaction paths for synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine from phenol, aniline and formaldehyde

Cited by 16 publications

References 29 publications

Synthesis of Benzoxazine-Based N-Doped Mesoporous Carbons as High-Performance Electrode Materials

Synthesis of Benzoxazine-Based N-Doped Mesoporous Carbons as High-Performance Electrode Materials

3,4-Dihydro-2H-1,3-benzoxazines and their oxo-derivatives - Chemistry and bioactivities

Ambient Preparation of Benzoxazine‐based Phenolic Resins Enables Long‐term Sustainable Photosynthesis of Hydrogen Peroxide

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