556053-57-7Relevant academic research and scientific papers
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.
BF 3 ·oEt 2 -Catalyzed Synthesis of anti -β-(N -Arylamino)-α-hydroxynitriles by Regio- And Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines
Lu, Yang,Xu, Chuangchuang,Xu, Jiaxi,Xu, Kaini
supporting information, p. 602 - 608 (2020/02/13)
A safe and convenient synthetic method to anti -β-(N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super- acid H[B(OEt)F 3], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti -β-(N -arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.
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
Oxygenophilic Lewis Acid Promoted Synthesis of 2-Arylindoles from Anilines and Cyanoepoxides in Alcohol
Xu, Chuangchuang,Xu, Jiaxi
, p. 14733 - 14742 (2018/11/27)
A convenient synthetic method to indoles from anilines and cyanoepoxides was developed under the catalysis of BF3·OEt2 or AlCl3 in alcohols. The reaction involves a tandem reaction of the regiospecific ring-opening of cyanoepoxides with anilines, elimination of cyanide, intramolecular aromatic electrophilic substitution, and water elimination. The Lewis acid generated protic acid is an efficient catalyst. The method features readily accessible starting materials, wide substrate scope, transition-metal-free environment, and regiospecificity in the ring-opening of cyanoepoxides.
