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Journal article
A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[ b ]thiophenes
Organic & biomolecular chemistry, Vol.19(18), pp.4107-4117
05/12/2021
PMCID: PMC8211089
PMID: 33978029
Web of Science ID: WOS:000640679700001
Abstract
In this study, a new environmentally benign iodine-mediated one-pot iodocyclization/alkylation strategy for the synthesis of benzo[b]thiophene derivatives starting from 2-alkynylthioanisoles was developed. The synthesis of a diverse population of 2,3-disubstituted benzo[b]thiophenes was achieved in high yields by employing moderate reaction conditions using 1,3-dicarbonyl substrates as the nucleophile and various substituted propargyl alcohols as both the cyclization precursor and the alkylating agent. This method resulted in the formation of a series of complex structures obtained in a single step. Additionally, a strategy was devised for the one pot iodocyclization/oxidation of propargyl alcohols into carbonyl functionalized benzo[b]thiophene structures. These green one-pot reaction processes were designed to reduce wastes and byproducts while generating a complex substitution pattern on the benzo[b]thiophene structure. The reported methodologies may be used to synthesize more functionalized benzo[b]thiophene structures that can be used in both biomedical and organic electronic applications.
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Details
- Title
- A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[ b ]thiophenes
- Publication Details
- Organic & biomolecular chemistry, Vol.19(18), pp.4107-4117
- Resource Type
- Journal article
- Publisher
- Royal Society of Chemistry (RSC); United Kingdom
- Grant note
- Funding for this research was provided by: Research Corporation for Science Advancement (23248) University of West Florida National Institute of General Medical Sciences (1T34GM110517-01)
- Copyright
- © Royal Society of Chemistry (RSC);
- Identifiers
- WOS:000640679700001; 99380480677306600
- Academic Unit
- Hal Marcus College of Science and Engineering ; Chemistry
- Language
- English