Affiliation:
1. East China University of Science and Technology Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education Shanghai Key Laboratory of New Drug Design
2. College of Biochemical Engineering, Beijing Union University
3. College of Pharmacy, Linyi University
Abstract
AbstractA one-pot, three-component reaction involving SNAr-decarboxylative redox isomerization starting from an electron-withdrawing group bearing fluorobenzaldehyde or fluorothiophenecarbaldehyde (electron-pair diacceptor), secondary amine, and trans-4-hydroxy-l-proline or indoline-2-carboxylic acid (electron-pair donor) has been developed to give N-[(pyrrolylmethyl)-substituted (het)aryl]- and N-[(indolylmethyl)-substituted (het)aryl]pyrrolidines, -piperidines, -morpholines, and -azocanes. The highlights of this protocol are its great convenience in the simultaneous construction of a C(sp2)–N bond and a C(sp3)–N bond with simple operation; the reaction can be performed on a gram scale. This efficient one-pot multicomponent reaction has potential as a novel method for drug synthesis, especially involving polycyclic compounds.
Funder
National Natural Science Foundation of China
Science and Technology Commission of Shanghai Municipality
Key Research and Development Project of Shandong Province
Subject
Organic Chemistry,Catalysis