46209-55-6Relevant academic research and scientific papers
Green synthesis method of methyl cyclopentenolone
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Paragraph 0049-0051, (2020/12/05)
The invention relates to a green synthesis method of methyl cyclopentenolone, and belongs to the field of organic synthesis. The method comprises the following synthesis steps: A, carrying out Mannichreaction on 2-methyl furan serving as a raw material and piperidine hydrochloride to generate an aminated intermediate; B, adding a catalytic amount of sulfuric acid into the aminated intermediate for reflux reaction to obtain a hydrolysate; and C, adding the hydrolysate into methylbenzene, neutralizing to be neutral by using sodium hydroxide, adding piperidine and pyridine, refluxing and separating water until no water is separated out, and rectifying to obtain a cyclized product; and D, putting the cyclized product into an acetic acid-hydrochloric acid solution for reflux reaction, cooling,removing piperidine hydrochloride, removing acetic acid from the filtrate, adding water, and crystallizing to obtain methyl cyclopentenolone. According to the method, the generation of wastewater andwaste salt is greatly reduced, the generated piperidine hydrochloride can be recycled and reused, and the method is a green synthetic method for synthesizing methyl cyclopentenolone.
The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles
Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 2941 - 2958 (2007/10/03)
Dichlorodimethylsilane and trichloromethylsilane have been used to generate iminium ions from aminals and aminol ethers derived from secondary alkylamines, including glycine derivatives, in aprotic media which were shown to undergo reactions with electron rich aromatic heterocycles, including furan, to give mono-aminoalkylation products in good yields. Whereas chlorotrimethylsilane has been shown to generate iminium ions from aminol ethers, no evidence was adduced for the involvement of iminium ions using aminals. 2,5-Disubstitution of N-methylpyrrole was the major result in reactions of N-methylpyrrole with aminals in the presence of chlorotrimethylsilane where no build up of hydrogen chloride occurs and where chlorotrimethylsilane can function catalytically. Experimental results, including the use of bis(trimethylsilyl)acetamide as a proton scavenger, and some relative rate data, are presented that allow possible mechanisms to be evaluated.
aminoalkylbenzotriazoles: Reagents for the aminoalkylation of electron rich heterocycles
Katritzky,Yang,Lam
, p. 4971 - 4978 (2007/10/02)
Secondary and tertiary aminoalkylbenzotriazoles react with pyrrole, indole, their N-methyl analogs and with 2-methylfuran under mild reaction conditions in the presence of a Lewis acid to afford selectively the corresponding secondary or tertiary amines.
MANNICH REACTIONS OF FURAN AND 2-METHYLFURAN USING PRE-FORMED IMONIUM SALTS
Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 2377 - 2380 (2007/10/02)
Good yields of 2-dialkylaminomethylfurans are obtained when N,N-dialkylmethylene-imonium chlorides are allowed to interact with furan in acetonitrile at room temperature; similar results are obtained using 2-methylfuran.
