Synthesis of 2,3-Disubstituted pyrroles by Lewis acid promoted cyclization of N-Sulfonyl vinylogous carbamates and amides

[Display omitted] A three-step sequence to construct pyrroles from three components including 2,2-dimethoxyethylamine, aryl/alkyl sulfonyl chlorides and alkynes bearing electron-withdrawing groups is presented. The pyrroles are proposed to arise via a 5-exo-trig cyclization proceeding through both o...

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Bibliographic Details
Published inTetrahedron letters Vol. 122; pp. 154507 - 154510
Main Authors Rustin, Gavin J., Donahue, Matthew G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.06.2023
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
ESTERS
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Summary:[Display omitted] A three-step sequence to construct pyrroles from three components including 2,2-dimethoxyethylamine, aryl/alkyl sulfonyl chlorides and alkynes bearing electron-withdrawing groups is presented. The pyrroles are proposed to arise via a 5-exo-trig cyclization proceeding through both oxocarbenium and N-sulfonyliminium ions. This modular route allows for the variability at the N-sulfonyl group, the C2 and C3 substituents for rational vectoring of the pyrrole nucleus for downstream processes.
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Author Contributions
MGD initially conceived the idea for this research. GJR carried out the research, acquired the data and analyzed the results. MGD and GJR wrote the manuscripts in a collaborative endeavor.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154507