Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles.
Journal
RSC advances
ISSN: 2046-2069
Titre abrégé: RSC Adv
Pays: England
ID NLM: 101581657
Informations de publication
Date de publication:
01 Oct 2019
01 Oct 2019
Historique:
received:
15
08
2019
accepted:
20
09
2019
entrez:
9
5
2022
pubmed:
7
10
2019
medline:
7
10
2019
Statut:
epublish
Résumé
2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesised using a Knorr-type approach from aliphatic starting materials. 2-Thionoester pyrroles were reduced to the corresponding 2-formyl pyrroles, or the deuterated formyl variant, in one step using RANEY® nickel, thereby removing the need for the much-utilised hydrolysis/decarboxylation/formylation steps that are typically required to convert Knorr-type 2-carboxylate pyrroles into 2-formyl pyrroles. 2-Thionoester pyrroles proved tolerant of typical functional group interconversions for which the parent 2-carboxylate pyrroles have become known.
Identifiants
pubmed: 35527977
doi: 10.1039/c9ra07527e
pii: c9ra07527e
pmc: PMC9072669
doi:
Types de publication
Journal Article
Langues
eng
Pagination
31773-31780Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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