A Three-Component Approach to (Hetero)arenes with Two N-Containing Heterocycle Motifs

Yuliang Zhang; Yang Zhang; Hong Qiu; Liqin Wang; Xizhen Ge; Zhen Wang; Xinhong Yu

doi:10.1055/a-1920-3041

Synthesis, Table of Contents

Synthesis 2022; 54(24): 5445-5450
DOI: 10.1055/a-1920-3041

paper

A Three-Component Approach to (Hetero)arenes with Two N-Containing Heterocycle Motifs

Authors

Yuliang Zhang‡

^aEast China University of Science and Technology Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education Shanghai Key Laboratory of New Drug Design, Shanghai 200237, P. R. of China
Yang Zhang‡

^aEast China University of Science and Technology Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education Shanghai Key Laboratory of New Drug Design, Shanghai 200237, P. R. of China
Hong Qiu

^aEast China University of Science and Technology Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education Shanghai Key Laboratory of New Drug Design, Shanghai 200237, P. R. of China
Liqin Wang

^aEast China University of Science and Technology Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education Shanghai Key Laboratory of New Drug Design, Shanghai 200237, P. R. of China
Xizhen Ge∗

^cCollege of Biochemical Engineering, Beijing Union University, Beijing 100023, P. R. of China
Zhen Wang∗

^bCollege of Pharmacy, Linyi University, Linyi 276000, P. R. of China
Xinhong Yu ∗

^aEast China University of Science and Technology Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education Shanghai Key Laboratory of New Drug Design, Shanghai 200237, P. R. of China

Abstract

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Abstract

A one-pot, three-component reaction involving S_NAr-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.

Key words

three-component reaction - one-pot reaction - S_NAr-decarboxylative redox isomerization - polycyclic compounds - N-alkyl pyrroles - N-alkyl indoles

Full Text

References

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Supplementary Material

Supporting Information (PDF)