The reaction occurs under very mild conditions catalyst. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. The polymerization of these monomers is observed for the first time and confirmed using. Pdf a simple and selective synthesis of 1,3benzoxazine2,4dione and 4 methylene1,3benzoxazine2one derivatives is reported from the reaction of. Files available from the acs website may be downloaded for personal use only. Synthesis and ringopening polymerization of 2substituted 1,3.
A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. The synthesis of both 2aryl and 2alkyl 1,3benzodioxin4one could be achieved under these conditions. Studies on some benzoxazine4one derivatives with potential biological activity. The complex reaction occurring during the synthesis of the monomers and polymerization makes studies of benzoxazine complex. Nsubstituted aminomethylphenol mannich base and 3,4dihydro2h3substituted 1,3benzoxazine benzoxazine were synthesized from substituted phenol pcresol, phenol, pchlorophenol, substituted aniline ptoluidine, aniline, pchloroaniline and formaldehyde to study influence of substituent on equilibrium of benzoxazine synthesis from mannich base and formaldehyde. Corresponding authors a department of materials and optoelectronic science, national sun yatsen university, kaohsiung 80424, taiwan email. A mild and high yielding process for synthesis of 1,3benzodioxin4ones and benzoxazine2,4diones has been developed using benzotriazole chemistry. Reactivity of 4h3,1benzoxazin4ones towards nitrogen. Journal of chemical and pharmaceutical research, 20, 57. Onepot synthesis of 2substituted 4 h 3,1benzoxazin4one. Direct synthesis of polybenzoxazine imide from an ortho. Herein, we report the synthesis of 2substituted 4h3,1benzoxazinones 1a and b via the reaction of freshly distilled acetic anhydride 19 andor isobutyroyl. Synthesis is done by grinding of 2 mmol of ketones, 2 mmol of malononitrile and 1 mmol of amines in a mortar at room temperature for 57 min.
The behavior of 2ethoxy4h3,1benzoxazin4one 1 towards nitrogen nucleophiles, e. The selective synthesis of those 1,3benzoxazine derivatives were found to be dependent on the type of substituents present on the schiff base. A mild and high yielding process for synthesis of 1,3benzodioxin 4 ones and benzoxazine2,4diones has been developed using benzotriazole chemistry. Pdf various synthetic methods of benzoxazine monomers.
A facile onestep synthesis of 1hbenzoxazine2,4diones from heterocyclic. Synthesis of some new 2,3disubstituted43hquinazolinone. All spectral data and spectrum are represented in additional file 1. The uses of 2ethoxy4h3,1benzoxazin4one in the synthesis of.
Pdf a simple and selective synthesis of 1,3benzoxazine2,4dione and 4methylene1,3benzoxazine2one derivatives is reported from the reaction of. Quinazolinones are interesting materials because of their valuable biological effects. Benzoxazine chemistry in solution and melt request pdf. A simple and selective synthesis of 1,3benzoxazine2,4dione and 4methylene1,3benzoxazine2one derivatives is reported from the reaction of schiff bases and triphosgene. The synthesis of benzoxazine is usually achieved by onepot mannich. Progress is made from a controlled, laboratory synthesis of benzoxazines in homogeneous solutions at modest to low concentrations to more high solid andor melt systems that are much more efficient for scaleup synthesis. In this study some new 2,3disubstituted43hquinqzolinone derivatives were synthesized from anthranilic acid in six steps by introducing a new chiral center to the aliphatic side chain of the quinazolinone. Simple and selective synthesis of 1,3benzoxazine derivatives. Influence of substituent on equilibrium of benzoxazine. The 1,4benzoxazine scaffold is thus a promising foundation for the. Pdf a new method has been designed to prepare the known benzoxazinone derivative 2nphthaloylmethyl4h3,1benzoxazin4one 4. Acid catalyzed synthesis and theoretical insight into the photochromic activity article pdf available in tetrahedron letters 5722 april 2016.
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