5697-44-9Relevant articles and documents
A Concise Route to 2-Sulfonylacetonitriles from Sodium Metabisulfite
Yao, Yanfang,Yin, Ziqing,Chen, Weiyun,Xie, Wenlin,He, Fu-Sheng,Wu, Jie
, p. 570 - 574 (2020/12/09)
A three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3-azido-2-methylbut-3-en-2-ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2-arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room temperature without the need of any catalysts or additives. Moreover, the synthetic utility of this method is demonstrated by the transformation of 2-arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-arylsulfonylethylamine. (Figure presented.).
Unexpected Aldehyde-Catalyzed Reaction of Imidazole N -Oxides with Ethyl Cyanoacetate
Efimova, Anna S.,Kutasevich, Anton V.,Kuz'Mina, Ludmila G.,Mityanov, Vitaly S.,Perevalov, Valery P.,Sizonenko, Marina N.
supporting information, p. 179 - 182 (2020/01/23)
The reaction of 2-unsubstituted imidazole N -oxides with ethyl cyanoacetate and aromatic aldehydes leads to the formation of ethyl 2-cyano-2-(1,3-dihydro-2 H -imidazole-2-ylidene)acetates. The reaction proceeds through an initial [3+2] cycloaddition, followed by cleavage of the cycloadduct and regeneration of the aldehyde, which essentially plays a catalytic role.
Reductive radical-initiated 1,2-C migration assisted by an azidyl group
Song, Jin-Na,Wang, Zikun,Zhang, Xueying,Zhang, Zhansong
, p. 7921 - 7926 (2020/08/19)
We report here a novel reductive radical-polar crossover reaction that is a reductive radical-initiated 1,2-C migration of 2-azido allyl alcohols enabled by an azidyl group. The reaction tolerates diverse migrating groups, such as alkyl, alkenyl, and aryl groups, allowing access to n+1 ring expansion of small to large rings. The possibility of directly using propargyl alcohols in one-pot is also described. Mechanistic studies indicated that an azidyl group is a good leaving group and provides a driving force for the 1,2-C migration. This journal is
Preparation method of sulfonyl acetonitrile compound
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Paragraph 0019-0022, (2020/08/30)
The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of sulfonyl acetonitrile compounds. The structure of the compound is characterized by 1H NMR, 13C NMR and other methods and is confirmed. The method comprises the following steps: taking 2, 2-dichloroethane as a solvent and aryl diazonium salt and sodium pyrosulfite (Na2S2O5) as a catalyst without metal catalyst, generating aryl sulfonyl free radicals on site at room temperature, carrying out free radical addition reaction on 3-azido-2-methylbutyl-3-ene-2-ol, and removing monomolecular nitrogen and 2-hydroxypropyl free radicals to obtain the sulfonyl acetonitrile compound. The preparation method of the sulfonyl acetonitrile compound has the advantages of being mild in condition, simple, efficient, high in reaction yield, wide in substrate application range, good in product purity, convenient to separate and purify and good in application value.
Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation
Zhou, Kaida,Liu, Jin-Biao,Xie, Wenlin,Ye, Shengqing,Wu, Jie
supporting information, p. 2554 - 2557 (2020/03/10)
Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, an aryl radical is generated in situ from aryl iodide, which undergoes subsequent sulfonylation via the insertion of sulfur dioxide leading to arylsulfonyl radical intermediates. Then the arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the corresponding 2-(arylsulfonyl)acetonitrile.
Radical cyanomethylation via vinyl azide cascade-fragmentation
Donald, James R.,Berrell, Sophie L.
, p. 5832 - 5836 (2019/06/17)
Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.
Alpha-cyano-aryl sulfonyl compounds and preparation method thereof
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Paragraph 0033; 0035-0036; 0039, (2018/10/19)
The invention discloses alpha-cyano-aryl sulfonyl compounds and a preparation method thereof. The structural general formula of the alpha-cyano-aryl sulfonyl compounds is described in the description;the concrete structures of the compounds are also described in the description. The method for synthesizing the alpha-cyano-aryl sulfonyl compounds by enabling aryl sulfonyl hydrazide to react with asolvent-acetonitrile under the oxidation of potassium persulfate is realized for the first time. According to the method, any catalyst and basic additive do not need to be added, and sulfur free radicals and carbon free radicals are constructed by using the potassium persulfate to separately oxidize the free radicals of the aryl sulfonyl hydrazide for denitrification and the acetonitrile for dehydrogenation; then, the synthesis of the target compounds, i.e., alpha-cyano-aryl sulfonyl can be effectively realized by means of free radical coupling. The method has the advantages of being mild inconditions, economical and practical, simple to operate, suitable for large-scale production, and the like.
An efficient synthesis of 2-aminothiophenes via the gewald reaction catalyzed by an N-methylpiperazine-functionalized polyacrylonitrile fiber
Ma, Lichao,Yuan, Liwei,Xu, Changzhu,Li, Guowei,Tao, Minli,Zhang, Wenqin
supporting information, p. 45 - 52 (2013/03/13)
A new N-methylpiperazine-functionalized polyacrylonitrile fiber has been developed to catalyze the Gewald reaction between 2,5-dihydroxy-1,4-dithiane and activated nitriles to afford 3-substituted 2-aminothiophenes in good to excellent yields (65-91%). Low catalyst loading (8.0 mol%), simple procedure, high yields, excellent recyclability, and reusability (up to 10 times with minimal loss of catalytic activity) are attractive features of this fiber catalyst. Georg Thieme Verlag Stuttgart · New York.
NOVEL DERIVATIVES OF PHENYLUREAS, INHIBITORS OF THE SOAT-1 ENZYME, PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM
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Page/Page column 21-22, (2009/04/25)
The present invention relates to compounds of formula (I) : as well as to cosmetic and pharmaceutical compositions containing such a compound.
THE VICARIOUS INTRAMOLECULAR SUBSTITUTION REACTIONS. I. SYNTHESIS OF CONDENSED INDOLIZINES BASED ON 2-QUINOXALYLACETONITRILES
Litvinenko, S. V.,Volovenko, Yu. M.,Babichev, F. S.
, p. 307 - 312 (2007/10/02)
The interaction of α-substituted 2-(3-chloro)quinoxalylacetonitriles with azines to give condensed indolizinoquinoxalines has been studied. A mechanism for the reaction has been proposed which includes an intramolecular vicarious substitution of hydrogen in the azolium salt nucleus. The limits of utility of the reaction have been determined and some chemical properties of the compounds synthesized have been studied.
