- Synthesis of Substituted Piperidines from N,N-Bis [(benzotriazol-1 -yl)methyl]amines
-
N,N-Bis[(benzotriazol-1-yl)methyl]benzylamines and N,N-bis[(benzotriazol-1-yl)methyl](p-N′,N′-dimethylphenyl)amine on reaction with allyltrimethylsilanes yielded substituted piperidines. Other N,N-bis[(benzotriazol-1-yl)methyl]anilines (unsubstituted and p-CH3, OCH3, Cl) gave julolidines (2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij] quinoline).
- Katritzky, Alan R.,Luo, Zhushou,Cui, Xi-Lin
-
-
Read Online
- A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines
-
We report that HCl·DMPU induces the formation of (thiomethyl)methyl carbenium ion from DMSO under mild conditions. Homoallylic amines react with this electrophile to generate 4-chloropiperidines in good yields. The method applies to both aromatic and aliphatic amines. The use of HCl·DMPU as both non-nucleophilic base and chloride source constitutes an environmentally benign alternative for piperidine formation. The reaction has a broad substrate scope, and the conditions offer good chemical yields with high functional group tolerance and scalability.
- Ebule, Rene,Mudshinge, Sagar,Nantz, Michael H.,Mashuta, Mark S.,Hammond, Gerald B.,Xu, Bo
-
p. 3249 - 3259
(2019/03/20)
-