51287-17-3Relevant articles and documents
Tailor-made and chemically designed synthesis of coumarin-containing benzoxazines and their reactivity study toward their thermosets
Froimowicz, Pablo,Rodriguez Arza, Carlos,Ohashi, Seishi,Ishida, Hatsuo
, p. 1428 - 1435 (2016)
Coumarins are used as a natural renewable resource to synthesize coumarin-containing benzoxazine resins. The coumarin-containing benzoxazines are fully characterized in terms of their chemical structure by Fourier-transform infrared spectroscopy and proto
Synthesis, characterization, and catalytic behavior of methoxy- and dimethoxy-substituted pyridinium-type ionic liquids
Manikandan, Chitrarasu,Ganesan, Kilivelu
, p. 3362 - 3367 (2014)
Synthesis of methoxy-substituted pyridinium-type ionic liquids from a nontoxic and easy method is described. Catalytic behaviors of synthesized ionic liquids were investigated with various concentrations for the Mannich reaction. We have observed that methoxy- and dimethoxy-substituted pyridinium bromides showed better catalytic behavior than other ionic liquids.
Benzoxazine miniemulsions stabilized with polymerizable nonionic benzoxazine surfactants
Sawaryn, Christian,Landfester, Katharina,Taden, Andreas
, p. 8933 - 8941 (2010)
For the first time, the concept of polymerizable nonionic benzoxazine surfactants is described. Different target structures with varying hydrophobic-lipophilic balance (HLB) values were synthesized and successfully tested for the miniemulsification of two N-aliphatic and N-aromatic benzoxazine resins. As a model system, the difunctional benzoxazine surfactant bis(3,4-dihydro-2H-3-(polypropyleneoxide-block-polyethyleneoxide-1, 3-benzoxazinyl)isopropane (B2000) was analyzed in detail via FT-IR, 1H NMR, surface tension measurements, and thermal analysis such as DSC and TGA. Additional to the colloidal stability of the benzoxazine miniemulsions, investigations focused on the surfactant copolymerization behavior and compatibility with other resins. It was found that despite the observed slow homopolymerization the described surfactants easily undergo copolymerization with the model benzoxazine resins.
Intrinsic self-initiating thermal ring-opening polymerization of 1,3-benzoxazines without the influence of impurities using very high purity crystals
Han, Lu,Salum, María Laura,Zhang, Kan,Froimowicz, Pablo,Ishida, Hatsuo
, p. 3434 - 3445 (2017)
A phenol/aniline type monofunctional benzoxazine monomer, PH-a, is synthesized and highly purified to study the intrinsic thermal ring-opening polymerization of benzoxazines without the influence of any impurity. The successful synthesis of the monomer and its corresponding chemical structure are confirmed by Fourier transform infrared spectroscopy (FTIR) and 1H nuclear magnetic resonance (1H NMR) spectroscopy. Purity of the compound is evaluated through differential scanning calorimetry (DSC) as well as elemental analysis (EA). Moreover, the thermal behavior of benzoxazine monomer toward polymerization is also studied by DSC, indicating that the highly purified benzoxazine monomer actually polymerize upon heating. The results present evidence of an intrinsic tendency for 1,3-benzoxazines to undergo thermally induced ring-opening polymerization upon heating only without any impurity participating during the reaction. This reveals that polybenzoxazines can be obtained by both the traditional thermally accelerated (or activated) polymerization, where impurities or purposefully added initiators are involved in the reaction; or, by the classic thermal polymerization, where only heat is enough to initiate the reaction.
Catalytic performance of benzoxazine derived ordered mesoporous carbon materials for the selective oxidation of 2-methylnaphthalene
Zang, Zhouxuan,Chang, Yingge,Yu, Yi,Zhang, Haihan,Xu, Li,Liu, Guoji
, p. 17422 - 17430 (2020)
2-Methylnaphthoquinone is an important chemical product. The catalyst used in the catalytic oxidation of 2-methylnaphthalene to 2-methylnaphthoquinone has been a research hotspot. In this paper, benzoxazine derived ordered mesoporous carbon materials were used as catalysts, and their catalytic performance in acetic acid/hydrogen peroxides was investigated. The N/S co-doped carbon material (NSCM) was prepared with thiourea-type benzoxazine as a carbon precursor and SBA-15 as a template. The nitrogen-doped carbon material (NCM) was prepared using the same method using aniline-type benzoxazine as a precursor. The carbon materials were characterized by N2 adsorption/desorption, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and Raman spectroscopy. The results have shown that both carbon materials exhibit worm-like structure and have graphitized amorphous structure. Nitrogen in the carbon materials existed in the form of pyridine nitrogen and pyrrole nitrogen, which caused the surface defects of carbon materials. The surface defects are critical for the enhancement of the catalytic activity of carbon materials. With NSCM and NCM as catalysts, the yields of 2-methylnaphthoquinone were 78.8% and 65.7%, respectively. By comparison, NSCM has higher catalytic activity, and the catalytic activity remains stable after five cycles of use. These results indicate that NSCM has great potential as a highly efficient catalyst for the selective oxidation of 2-methylnaphthalene. This journal is
Screening of simple carbohydrates as a renewable organocatalyst for the efficient construction of 1,3-benzoxazine scaffold
Y?ld?r?m, Ayhan,Kaya, Yunus,G?ker, Mustafa
, (2021/10/12)
A convenient protocol for the two component preparation of 1,3-benzoxazines by using several protected and unprotected carbohydrate molecules as organocatalysts have been developed which is broadly applicable to condensation reaction between variety of Ma
Synthesis of arylidene-based benzoxazine derivatives as promising antimicrobial materials
Al-Ghamdi, Youssef O.,Alamry, Khalid A.,Alzahrani, Abdullah Y.,Elfaky, Mahmoud A.,Hussein, Mahmoud A.,Hussien, Mostafa A.,Musa, Abdulrahman
supporting information, (2021/12/10)
The current study is focused on the synthesis of two novel arylidene-based benzoxazines namely: 3-(3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)-1-(thiophen-2-yl)-2-propenone (PTP), and 3-(3-phenyl-3,4-dihydro-2H-benzo[e][1,3]-oxazin-6-yl)-1-(pyridin-2-yl)-2-propenone (PPP). The benzoxazines were obtained as condensation products of the reaction of each of the phenol analogs: [3-(4-hydroxyphenyl)-1-(2-thiophenyl)-2-propenone] (HTP), and [3-(4-hydroxyphenyl)-1-(2-pyridinyl)-2-propenone] (HPP), with aniline, and paraformaldehyde, respectively. PTP and PPP were structurally confirmed using analysis such as ultraviolet (UV) spectroscopy, together with FTIR, and 1H-NMR and 13C-NMR spectral analyses, respectively. The benzoxazine derivatives revealed an excellent antimicrobial activity against the selected bacterial (including Gram-positive & Gram-negative) and fungi. The antimicrobial activity was also investigated using the agar diffusion approach. The qualitative assay of the biological study from the inhibition zones for the PTP, PPP, and PBO revealed interesting results. The examinations revealed some levels of antimicrobial efficacy against the selected bacterial strains used. However, the biological efficacy of PTP appeared to be better with larger zones of inhibition against the growth of the micro-organisms. Moreover, the molecular docking studies of PTP, PPP, and PBO derivatives were screened against the “5FSA” protein. PPP derivative displayed a good activity than the other derivatives PTP and PBO in docking with 5FSA protein. The obtained values were ?7.34, ?7.70, and ?5.70 Kcal/Mol for PPP, PTP, and PBO respectively compared to Fluconazole reference value ?7.86 Kcal/Mol.
N-alkyl imidazole-based homonuclear coordination complex as a neutral organocatalyst for the faster and efficient construction of 3,4-dihydro-2H-1,3-oxazine scaffold
Y?ld?r?m, Ayhan,G?ker, Mustafa
, (2021/08/26)
In the present work, homonuclear coordination complex including Zn (II) and N-hexadecylimidazole ligand was used for the first time as a highly efficient homogeneous neutral organocatalyst for the synthesis of 3,4-dihydro-2H-1,3-benzoxazine monomers. Ther
Nano-Fe3O4?walnut shell/Cu(ii) as a highly effective environmentally friendly catalyst for the one-potpseudothree-component synthesis of 1,3-oxazine derivatives under solvent-free conditions
Fatemeh Mirjalili, Bi Bi,Tafti, Arefeh Dehghani
, p. 31874 - 31880 (2020/09/21)
Fe3O4?walnut shell/Cu(ii) as an eco-friendly bio-based magnetic nano-catalyst was prepared by adding CuCl2to Fe3O4?walnut shell in alkaline medium. A series of 2-aryl/alkyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines were synthesized by the one-potpseudothree-component reaction of β-naphthol, formaldehyde and various amines using nano-Fe3O4?walnut shell/Cu(ii) at 60 °C under solvent-free conditions. The catalyst was removed from the reaction mixture by an external magnet and was reusable several times without any considerable loss of its activity. This protocol has several advantages such as excellent yields, short reaction times, clean and convenient procedure, easy work-up and use of an eco-friendly catalyst.
Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions
Deliballi, Zeynep,Kiskan, Baris,Yagci, Yusuf
, p. 2354 - 2361 (2020/04/10)
Simple benzoxazines were mixed and reacted with various phenolics such as phenol, p-nitrophenol, p-cresol, 1,3-dihyroxybenzene (resorcinol), 1,3,5-trihydroxybenzene (phloroglucinol), and N-(2-hydroxyphenyl)benzamide. The influence of these phenolic compou
