5589-60-6Relevant academic research and scientific papers
Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines
Chen, Cheng-Yi,He, Fengxian,Tang, Guangrong,Yuan, Huiqing,Li, Ning,Wang, Jinmin,Faessler, Roger
, p. 2395 - 2401 (2018/02/23)
An efficient synthesis of quinazolines based on an iron-catalyzed C(sp3)-H oxidation and intramolecular C-N bond formation using tert-BuOOH as the terminal oxidant is described. The reaction of readily available 2-alkylamino benzonitriles with various organometallic reagents led to 2-alkylamino N-H ketimine species. The FeCl2-catalyzed C(sp3)-H oxidation of the alkyl group employing tert-BuOOH followed by intramolecular C-N bond formation and aromatization afforded a wide variety of 2,4-disubstituted quinazolines in good to excellent yields.
Borrowing Hydrogen Methodology for N-Benzylation using a π-Benzylpalladium System in Water
Hikawa, Hidemasa,Koike, Toshitaka,Izumi, Kyoko,Kikkawa, Shoko,Azumaya, Isao
, p. 784 - 791 (2016/03/09)
We demonstrate a borrowing hydrogen methodology using the unique reactivity of the π-benzylpalladium system in water, which offers an efficient and environmentally friendly N-monobenzylation of electron-deficient anilines or 2-aminopyridine with non-activated benzylic alcohols under neutral conditions. The crossover experiment using benzyl-α,α-d2 alcohol and 3-methylbenzyl alcohol afforded H/D scrambling products, suggesting that the borrowing hydrogen pathway occurred in our catalytic system. Our simple protocol can accomplish a gram scale reaction of 2-aminobenzonitrile (76 % isolated yield), and is performed with the use of only 1 mol % Pd(OAc)2 and 2 mol % TPPMS without other additives in water.
