130539-99-0Relevant articles and documents
Method for preparing N-(5-methyl furfuryl)benzylamine through one-pot method
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Paragraph 0022; 0026; 0027; 0039, (2018/04/03)
A preparation method of N-(5-methyl furfuryl)benzylamine. The preparation method comprises the following steps: sequentially adding a multi-phase hydrogenation catalyst, 5-methyl furfural, a solvent and benzylamine in a reaction vessel, stirring under a hydrogen atmosphere of which the pressure ranges from normal pressure to 2.0Mpa and the reaction temperature ranging from normal temperature to 100 DEG C, reacting for 0.2 to 0.3 hour, and separating the catalyst and a product. According to the preparation method disclosed by the invention, an operation process is simplified, material loss brought by intermediate steps can be avoided, and maximum utilization of resources is realized; under a proper technological condition, the reaction time is greatly shortened, the production cost is reduced, and the production efficiency is increased; reaction is carried out under a mild condition, requirements on production equipment are not high, and the principle of safety production is met.
Method for preparing N-(5-methylfurfuryl)aniline and derivatives from biomass carbohydrate
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Paragraph 0056; 0057, (2018/07/30)
The invention discloses a method for preparing N-(5-methylfurfuryl)aniline and derivatives from biomass carbohydrate. The method comprises the following steps: sequentially adding biomass carbohydrate, phosphorous acid, distilled water, hydrogen iodide and an organic solvent to a reaction container; stirring at a normal pressure and a temperature of 30-120 DEG C; reacting for 0.2-5 h; separating atwo-phase solvent; successively extracting and washing an organic layer with sodium sulfite, sodium hydroxide and a saturated salt solution for multiple times; collecting an organic phase to be dewatered by anhydrous magnesium sulfate; sequentially adding a multiphase hydrogenation catalyst, the additional solvent, aniline or aniline derivatives; stirring in a hydrogen atmosphere of normal pressure to 2.0 MPa and at a temperature of normal temperature to 100 DEG C; reacting for 0.2-3.0 h; and separating products. The method provided by the invention mainly uses renewable biomass carbohydrateas the raw material, is completed by two steps so as to be simple to operate and avoid loss of materials caused by intermediate steps, is performed under normal pressure and mild conditions without noble metal catalyst so as to reduce production costs, and has low requirements on equipment.
Aryne cycloaddition with 3-oxidopyridinium species
Ren, Hailong,Wu, Chunrui,Ding, Xiuxiu,Chen, Xiaoge,Shi, Feng
supporting information, p. 8975 - 8984,10 (2012/12/12)
The [3 + 2] cycloaddition of arynes with 3-oxidopyridinium species is examined using the Kobayashi benzyne precursor. The reaction affords a bicyclo[3.2.1] skeleton under mild conditions. A [7 + 2] cycloaddition mode with a subsequent pyridine ring-opening event has also been observed.
Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives
Zaytsev,Mikhailova,Airiyan,Galkina,Golubev,Nikitina,Zubkov,Varlamov
, p. 505 - 513 (2012/10/29)
The regio- and stereoselectivity of the [4+2] cycloaddition of maleic, citraconic, dichloromaleic, and dibromomaleic anhydrides to difurfuryl amines and secondary furfurylamines were studied. N-Furfuryl-, N-phenyl-, and N-benzylhexahydrooxoepoxyisoindole-7-carboxylic acids were synthesized. An approach was developed for obtaining hexahydroepoxyoxoisoindole-7-carboxylic acid unsubstituted at the nitrogen atom. Aromatization of the oxabicycloheptene fragment of the dihaloepoxyiso-indolonecarboxylic acids gave a series of 7-carboxy-2-R-isoindol-1-ones.
Skeletal Wagner-Meerwein rearrangement of perhydro-3a,6;4,5- diepoxyisoindoles
Zubkov, Fedor I.,Zaytsev, Vladimir P.,Nikitina, Eugeniya V.,Khrustalev, Victor N.,Gozun, Sergey V.,Boltukhina, Ekaterina V.,Varlamov, Alexey V.
, p. 9148 - 9163 (2011/12/01)
An investigation of a skeletal Wagner-Meerwein rearrangement of variously substituted or quinoline-annulated 3a,6;4,5-diepoxyisoindol-1-ones is reported. Optimum reaction conditions (Ac2O, BF3·OEt 2, rt) were discovered fo
Intra-molecular Diels-Alder reactions of citraconamic acids from furfurylamines and citraconic anhydride: Effects of substitution in the furan ring on regioselectivity
Murali, Rajappa,Surya Prakash Rao,Scheeren, Hans W
, p. 3165 - 3174 (2007/10/03)
Regioselectivity in the intra-molecular Diels-Alder (IMDA) reaction of furfurylcitraconamic acids derived from N-benzylfurfurylamines and citraconic anhydride can be controlled by substituents located in the furan ring and by reaction conditions. Reactions conducted under kinetic conditions resulted in cycloaddition products having methyl and aminomethylene substituent in 1,3-relationship whereas under thermodynamic conditions, excepting in the case of the 3-methylsulfanyl group, the products rearranged to more stable cycloadducts in which the substituents are in 1,2-relationship. Product formation can be explained on the basis of frontier orbital interactions and steric considerations.
The use of bis(aminol) ethers derived from aliphatic primary amines in the synthesis of secondary and tertiary amines
Heaney, Harry,Papageorgiou, George
, p. 3473 - 3486 (2007/10/03)
A series of bis(aminol) ethers were prepared from primary aliphatic amines and benzylamine together with formaldehyde and either ethanol or methanol; they were reacted with electrophiles to give N-alkyl-N-alkoxymethyl-methyleneiminium salts which gave mixtures of secondary and tertiary amines in reactions with electron rich aromatic compounds: sequential reactions with two different nucleophiles gave the expected tertiary amines.
A new route to secondary amines from bis-(alkoxymethyl)-alkylamines - The activation of an aminomethyl group and protection of the product by the same functional group
Earle, Martyn J.,Fairhurst, Robin A.,Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 4229 - 4232 (2007/10/02)
Treatment of N,N-bis(alkoxymethyl)alkylamines with a variety of acidic reagents affords good yields of N-alkoxymethyl-N-alkylmethyleneiminium salts which react with trimethylsilyl enol ethers, and nucleophilic aromatic substrates to form protected secondary amines or tertiary amines by domino reactions; silyl ketene acetals afford tertiary amines only.
