Pentaleno[1,2‑c]pyrroles: Tricyclic 5/5/5 Fused Rings

A novel method for the preparation of tetrahydropentaleno­[1,2-c]­pyrroles (8) is described via the reaction of anilines with 1-en-4-yn-3-ols in the presence of Lewis acid. Oxidation of 8 with Br2 gave pentaleno­[1,2-c]­pyrroles (10), which is the first reported tricyclic 5/5/5 ring with a fully con...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 1; pp. 732 - 738
Main Authors Chen, Shu Kai, Hsu, Ming-Tsung, Liu, Yi-Hung, Liu, Shiuh-Tzung
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.01.2023
Subjects
Crystallography, X-Ray
Molecular Structure
Oxidation-Reduction
Pyrroles - chemistry
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Summary:A novel method for the preparation of tetrahydropentaleno­[1,2-c]­pyrroles (8) is described via the reaction of anilines with 1-en-4-yn-3-ols in the presence of Lewis acid. Oxidation of 8 with Br2 gave pentaleno­[1,2-c]­pyrroles (10), which is the first reported tricyclic 5/5/5 ring with a fully conjugated system. Structures of these obtained compounds were characterized by spectroscopic methods, and compounds 8a,b and 10c were further confirmed by X-ray crystallographic determination.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02405