51072-85-6Relevant articles and documents
Anomalous Dehydration of 2-Phenylindole-3-carboxamide to 2-Phenylindole-3-carbonitrile by Lithium Aluminium Hydride
Abraham, Tonson,Sicree, Albert J.
, p. 1063 - 1066 (1982)
Steric factors have been shown to be responsible for the anomalous dehydration of 2-phenylindole-3-carboxamide (1) to 2-phenylindole-3-carbonitrile (3) by lithium aluminium hydride.This steric effect was also reflected in the reactions of 2-phenylindole (
Mn(III)-Mediated Radical Cyclization of o-Alkenyl Aromatic Isocyanides with Boronic Acids: Access to N-Unprotected 2-Aryl-3-cyanoindoles
Liu, Lu,Li, Lei,Wang, Xin,Sun, Ran,Zhou, Ming-Dong,Wang, He
, p. 5826 - 5830 (2021/08/18)
The synthesis of N-unprotected 2-aryl-3-cyanoindoles was realized via the Mn(III)-mediated radical cascade cyclization of o-alkenyl aromatic isocyanides with boronic acids. A possible mechanism involving a sequential intermolecular radical addition, intramolecular cyclization, and cleavage of the C-C bond under mild reaction conditions is proposed. Mechanism studies show that H2O or O2 might provide the oxygen source for the elimination of benzaldehyde.
GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide
Wang, Xue,Makha, Mohamed,Chen, Shu-Wei,Zheng, Huaiji,Li, Yuehui
, p. 6199 - 6206 (2019/05/24)
An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.
