33984-97-3Relevant articles and documents
BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles
Xu, Chuangchuang,Xu, Jiaxi
supporting information, p. 127 - 134 (2019/12/26)
Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.
Metal-free and regiospecific synthesis of 3-arylindoles
Xie, Wenlai,Xu, Chuangchuang,Xu, Jiaxi
, p. 2661 - 2671 (2020/04/17)
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri
ALPHA-HYDROXY-BETA-AZIDO-TETRAZOLES
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Paragraph 0249; 0250, (2017/09/25)
Alpha-hydroxy-beta-azido tetrazole compounds of formula (I): a process for manufacturing alpha-hydroxy-beta-azido tetrazoles of formula (I), and their use for synthesizing new compounds, e.g. in “click” chemistry.