The chlorination of thiophene‐2‐aldehyde and ethyl thiophene‐2‐carboxylate in the presence of excess aluminum chloride

Iriarte, José; Martinez, E.; Muchowski, Joseph M.

doi:10.1002/jhet.5570130241

Cited by 19 publications

(1 citation statement)

References 3 publications

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“…25 The same method, except for the use of a longer reaction time (4 days), was applied to 2-chloroand 3-chIorothiophene to yield 5-chloro-2-thiophenealdehyde26 (59%) and 3-chloro-2-thiophenealdehyde27 (53%), respectively. 4-Chloro-2-thiophenealdehyde was obtained by chlorination of 2-thiophenealdehyde according to the method of Iriarte et al 28 The same method applied to 3-chloroand 5-chloro-2-thiophenealdehyde afforded 3,4-dichloro-2- was obtained following the method of Profit and Solft.27 l-(2-Thienyl)-2-nitropropenes 2a-g. General Method. A mixture of the corresponding aldehyde (0.1 mol), nitroethane (7.5 g, 0.1 mol), and n-butylamine (1 mL) was heated for 2 weeks at 50-60 °C in a well-closed flask.…”

Section: Methodsmentioning

confidence: 99%

Effects of thiophene analogs of chloroamphetamines on central serotonergic mechanisms

Conde¹,

Madronero²,

Fernandez-Tome³

et al. 1978

J. Med. Chem.

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Ring-chlorinated thienylisopropylamines, thiophene analogues of chloroamphetamines, have been synthesized and their effects on serotonergic mechanisms in the rat brain have been evaluated. With 4,5-dichlorothienylisopropylamine (3e), a pharmacological profile similar to that of p-chloroamphetamine, consisting in a marked and long-lasting serotonin depletion and a rather strong and prolonged inhibition of synaptosomal uptake of serotonin, was found. Chloro substitution in position C3 of the thiophene ring did not determine brain serotonin depletion nor serotonin uptake inhibition but enhanced brain MAO inhibitory activity present in all these compounds. 3,5-Dichlorothienylisopropylamine (3g) was the only compound of the series in which the inhibition of serotonin uptake was more marked than the serotonin depleting property.

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Section: Methodsmentioning

confidence: 99%