Preparation and properties of some 3-acetyl- and 3-formyl-5-halogenobenzo[b]thiophens

doi:10.1039/J39670002084

Paper

Preparation and properties of some 3-acetyl- and 3-formyl-5-halogenobenzo[b]thiophens

Published 1967 · M. Shanta, R. M. Scrowston

Journal of The Chemical Society C: Organic

UNKNOWN SJR score

7

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0

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Abstract

5-Chloro- and 5-bromo-benzo[b]thiophen-3-carbaldehydes were prepared from the corresponding 3-bromomethyl compound, either by the Sommelet reaction (65% yield) or by the Krohnke reaction (30% yield). They had the usual properties of an aromatic aldehyde; in particular, they underwent the Doebner reaction with malonic acid, and formed crystalline condensation products with rhodanine.Friedel–Crafts acetylation of 5-chloro- or 5-bromo-benzo[b]thiophen gave predominantly the 3-acetyl derivative. This reacted with dimethylamine hydrochloride and formaldehyde (Mannich reaction) to give the corresponding keto-amine, the keto-group of which was reduced with sodium borohydride. The resulting alcohols were treated with thionyl chloride to give the corresponding substituted 3-chloropropylamines.

Study Snapshot

3-acetyl-5-halogenobenzo[b]thiophen-3-carbaldehydes show promising properties for synthesis of novel compounds with rhodanine, and can be converted into 3-chloropropylamines by thionyl chloride treatment.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Preparation and properties of some 3-acetyl- and 3-formyl-5-halogenobenzo[b]thiophens

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References

Citations

Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes

This study demonstrates a novel approach for producing unique substituted 4-chlorobenzothiophenes, which can be used in various cross-coupling reactions for synthesis of novel compounds.

Synthesis of new 5‐substitutedbenzo[b]thiophene derivatives

This study successfully synthesized new 3-acyl-5-substituted benzo[b]thiophene derivatives with various substituents, aiming to create new antidepressants with dual mode of action.

Synthesis of new 4‐quinolone‐type compounds in the benzo[b]thiophene series

New 4quinolone-type compounds 5 and 13 were successfully synthesized by using an original "amination" reaction, which allows for the construction of pyridine rings from 2-aminobenzo[b]thiophene derivatives.

Synthesis of substituted benzo[b]thiophenes by acid-catalyzed cyclization of thiophenylacetals and ketones

This method efficiently synthesizes substituted benzo[b]thiophenes at lower temperatures and with limited PPA usage, compared to literature procedures.

New 3-[4-(aryl)piperazin-1-yl]-1-(benzo[b]thiophen-3-yl)propane derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants.

New 3-[4-(aryl)piperazin-1-yl]-1-(benzo[b]thiophen-3-yl)propane derivatives show potential as a new class of antidepressants with dual activity at 5-HT1A serotonin receptors and serotonin transport

Recent Advances in the Chemistry of Benzo[b]thiophenes

Benzo[b]thiophene chemistry has advanced significantly since 1952, with improved methods for preparing various benzo[b]thiophenes and their applications in various fields.