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

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

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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

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References

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