117873-01-5Relevant articles and documents
2-(N-Methylanilino)-2-phenylsulfanylacetonitrile, A Reagent Tested for Electrophilic, Nucleophilic, and Radical Reactions
Chen, Chih-Cheng,Chen, Same-Ting,Chuang, Tsung-Hsun,Fang, Jim-Min
, p. 2217 - 2222 (1994)
2-(N-Methylanilino)-2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide.Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates.Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by CuI or Lewis acids to give varied α-amino nitriles.The 4-oxo-2-aminonitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung.When 1 was treated with tributylstannane, the corresponding amino nitrile α-radical was formed and the self-coupling product was isolated.
Use of α-Anilino Dienenitriles as Nucleophiles in Cycloadditions
Fang, Jim-Min,Yang,Chau-Chen,Wang, Yu-Wen
, p. 477 - 481 (2007/10/02)
The α-anilino dienenitriles 1-5 were prepared.The dienes 1-3 reacted with dichlorocarbene and electrophiles containing electron-deficient double bonds such as maleic anhydride, benzoquinone, dimethyl acetylenedicarboxylate, tetracyanoethylene, and chlorosulphonyl isocyanate.The diarylmethylamines 8-10, generated by cycloaddition of α-anilino dienenitriles and maleic anhydride, were successfully transformed into acridones 15-17.Intramolecular cyclization of trienes 4 and 5 yielded the carbazoles and dihydro derivatives, accompanied by formation of 2-cyano-1-methylindole.