1242419-91-5Relevant academic research and scientific papers
Ln[N(SiMe3)2]3-Catalyzed Cross-Diinsertion of C≡N/C≡C into an N-H Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles
Hong, Longcheng,Shao, Yinlin,Zhang, Lixin,Zhou, Xigeng
supporting information, p. 8551 - 8555 (2014/07/21)
A lanthanide-catalyzed sequential insertion of C≡N and C≡C into an N-H bond is presented. The convenient reaction, which proceeds under mild conditions, is an efficient method for preparing 1,2,4-trisubstituted imidazoles directly from readily available propargylamines and nitriles.
Atom-economical synthesis of N-heterocycles via cascade inter-/intramolecular C-N Bond-forming reactions catalyzed by Ti amides
Shen, Hao,Xie, Zuowei
supporting information; experimental part, p. 11473 - 11480 (2010/10/02)
Direct and efficient catalytic reactions with excellent regioselectivity for the preparation of a series of substituted isoindoles, isoquinolines, and imidazoles are reported. Reaction of C6H4(2-CN)C≡C-R with an array of amines, catalyzed by 10 mol % of [σ:η1: η5-(OCH2)(Me2NCH2)C 2B9H9]Ti(NMe2) (1), gives a series of substituted isoindoles in very high yields. In a similar manner, interaction of C6H4(2-CH2CN)C≡C-Ph with various kinds of amines affords a wide range of substituted isoquinolines. On the other hand, treatment of propargylamines (R′C≡CCH2NHR′′) with nitriles in the presence of 10 mol % of 1 produces a class of substituted imidazoles in high yields. A possible reaction mechanism is proposed, involving sequential inter- and intramolecular C-N bond formation via hydroamination/ cyclization reaction of cyanoalkynes with amines or nitriles with propargylamines catalyzed by titanium amides.
