1334499-91-0Relevant articles and documents
Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU
Kang, Soosung,Kim, Hee-Kwon,La, Minh Thanh,Tran, Van Hieu
, p. 5008 - 5016 (2020/07/30)
A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.
Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3
La, Minh Thanh,Kang, Soosung,Kim, Hee-Kwon
, p. 6689 - 6696 (2019/06/14)
A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.
Boron trifluoride-mediated synthesis of N-aryl-substituted pyrrolidines from tetrahydrofuran and amines
Hu, Shanshan,Huo, Yan,Wang, Zhihong
, p. 1365 - 1368 (2018/01/27)
[Figure not available: see fulltext.] Boron trifluoride-mediated transformation of tetrahydrofuran to corresponding N-aryl-substituted pyrrolidines is conducted under mild reaction conditions, providing a practical synthetic method with reasonable yields. Computational studies confirmed the reaction mechanism involving a fast Lewis acid-assisted ring-opening step, followed by the 7-membered intermediate formation and a ringclosing process as the rate-determining step.