The title compound(C12H16N2)was synthesized by the reaction of o-phenylenediamine(I)and acetone(II)which was accelerated by microwave irradiation and catalyzed by acetic acid under solvent-free condition.The optimal c...The title compound(C12H16N2)was synthesized by the reaction of o-phenylenediamine(I)and acetone(II)which was accelerated by microwave irradiation and catalyzed by acetic acid under solvent-free condition.The optimal conditions are as follow:n(I):n(II)=1:1.2(I 1.08g,II 1.22 g),acetic acid 2 mL,time of microwave irradiation 10 min,and microwave power 320 W.The title compound was characterized by IR spectrogram and NMR spectra.The crystal structure was determined by X-ray single crystal diffraction.The title compound belongs to orthorhombic system with space group Pna2(1),Mr=189.28,a=1.22502(14),b=0.73344(8),c=1.20112(14)nm,V=1.0792(2)nm3,Z=4,Dc=1.165 g/cm3,F(000)=412,μ=0.070 mm-1,GOF =0.999,R1=0.0358,wR2 = 0.1087(I > 2σ(I)).展开更多
An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recy...An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium;carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives;and oxygen as an oxidant.The selenium-catalyzed oxidative carbonylation reaction of2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to afford l,4-dihydro-2H-3,l-benzoxazin-2-one in 87%yield.Furthermore,the selenium catalyst was readily recovered and recycled,affording a product yield of 80%after five cycles.展开更多
As benzoxazin-4-ones and quinazolines linked to indole nucleus acting as a good pharmacophore, the synthesis of these compounds has significant meaning. The key intermediates 2-（2＇, 5＇-disubstituted-indol-2＇-yl...As benzoxazin-4-ones and quinazolines linked to indole nucleus acting as a good pharmacophore, the synthesis of these compounds has significant meaning. The key intermediates 2-（2＇, 5＇-disubstituted-indol-2＇-yl）-4H-3, 1-benzoxazin-4-ones （3） were synthesized from cyclocondensation of indole-2-carbonyl chlorides （2） and anthranilic acid. Compound （3） on reaction with thiosemicarbazide and o-phenylene diamine afforded the compound （4） and （6） respectively. Compound （4） subjected to intramolecular cyclization under thermal conditions above its melting point afforded the compound （5）. Similarly compound （3） on fusion with o- phenylene diamine gave compound （7）. Structures of these compounds were confirmed by their spectral studies. The compounds were screened for their antimicrobial activity and the results were reported.展开更多
文摘The title compound(C12H16N2)was synthesized by the reaction of o-phenylenediamine(I)and acetone(II)which was accelerated by microwave irradiation and catalyzed by acetic acid under solvent-free condition.The optimal conditions are as follow:n(I):n(II)=1:1.2(I 1.08g,II 1.22 g),acetic acid 2 mL,time of microwave irradiation 10 min,and microwave power 320 W.The title compound was characterized by IR spectrogram and NMR spectra.The crystal structure was determined by X-ray single crystal diffraction.The title compound belongs to orthorhombic system with space group Pna2(1),Mr=189.28,a=1.22502(14),b=0.73344(8),c=1.20112(14)nm,V=1.0792(2)nm3,Z=4,Dc=1.165 g/cm3,F(000)=412,μ=0.070 mm-1,GOF =0.999,R1=0.0358,wR2 = 0.1087(I > 2σ(I)).
基金supported by the Program for Changjiang Scholars and Innovative Research Team in University(IRT1061)the Program for Innovative Research Team in Science and Technology in University of Henan Province(15IRTSTHN003)+1 种基金the Young Backbone Teachers Training Fund of the Education Department of Henan Province(2013GGJS-059)Henan Normal University(2011-8)
文摘An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium;carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives;and oxygen as an oxidant.The selenium-catalyzed oxidative carbonylation reaction of2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to afford l,4-dihydro-2H-3,l-benzoxazin-2-one in 87%yield.Furthermore,the selenium catalyst was readily recovered and recycled,affording a product yield of 80%after five cycles.
文摘As benzoxazin-4-ones and quinazolines linked to indole nucleus acting as a good pharmacophore, the synthesis of these compounds has significant meaning. The key intermediates 2-（2＇, 5＇-disubstituted-indol-2＇-yl）-4H-3, 1-benzoxazin-4-ones （3） were synthesized from cyclocondensation of indole-2-carbonyl chlorides （2） and anthranilic acid. Compound （3） on reaction with thiosemicarbazide and o-phenylene diamine afforded the compound （4） and （6） respectively. Compound （4） subjected to intramolecular cyclization under thermal conditions above its melting point afforded the compound （5）. Similarly compound （3） on fusion with o- phenylene diamine gave compound （7）. Structures of these compounds were confirmed by their spectral studies. The compounds were screened for their antimicrobial activity and the results were reported.
