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Synthesis 2022; 54(24): 5445-5450
DOI: 10.1055/a-1920-3041
DOI: 10.1055/a-1920-3041
paper
A Three-Component Approach to (Hetero)arenes with Two N-Containing Heterocycle Motifs
We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 21476078), Science and Technology Commission of Shanghai Municipality (No. 12431900902) and the Key Research and Development Project of Shandong Province (No. 2017YYSP027).
Abstract
A 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.
Key words
three-component reaction - one-pot reaction - SNAr-decarboxylative redox isomerization - polycyclic compounds - N-alkyl pyrroles - N-alkyl indolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1920-3041.
- Supporting Information
Publication History
Received: 08 June 2022
Accepted after revision: 08 August 2022
Accepted Manuscript online:
08 August 2022
Article published online:
09 September 2022
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For recent reports on the synthesis of pyrroles, see:
For recent examples, see:
For reports on MCRs, see:
For recent reports on the synthesis of the N-alkyl pyrroles through redox isomerization reactions, see refs. 4b and 6b and:
For reports on the synthesis of the N-alkyl pyrroles through MCRs, see: