1242419-80-2Relevant academic research and scientific papers
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.
