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Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles.

ABSTRACT: 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.

SUBMITTER: Kim MJ

PROVIDER: S-EPMC9072669 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles.

Kim Min Joon MJ Gaube Sophie M SM Beh Michael H R MHR Smith Craig D CD Thompson Alison A

RSC advances 20191007 54

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 ...[more]

PMID: 35527977

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