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.).
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
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.