ChemInform Abstract: Direct Formation of Functionalized Ketones via the Coupling of Functionalized Organocopper Reagents with Acid Chlorides.

Background: Agro-waste derived solvent media act as a greener process for the peptide bond formation using Nα - Fmoc-amino acid chloride and amino acid ester salt with in situ neutralization and coupling under biphasic condition. The Fmoc-amino acid chlorides are prepared by the reported procedure of freshly distilled SOCl2 with dry CH2Cl2. The protocol found many added advantages such as neutralization of amino acid ester salt and not required additional base for the neutralization, and directly coupling take place with Fmoc-amino acid chloride gave final product dipeptide ester in good to excellent yields. The protocol occurs with complete stereo chemical integrity of the configuration of substrates. Here, we revisited Schotten-Baumann condition, instead of using inorganic base. Objective: To develop green protocol for the synthesis of peptide bond using Fmoc-amino acid chloride with amino acid esters salt. Methods: The final product isolated is analyzed in several spectroscopic and analytical techniques such as FT-IR, 1H-, 13CNMR, Mass spectrometry and RP-HPLC to check stereo integrity and purity of the product. Conclusion: The present method developed greener using natural agro-waste (lemon fruit shell ash) derived solvent medium for the reaction and not required chemical entity.

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Noncataleptic neuroleptic agents: 2-(4-(2-(2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)ethyl)piperazine-1-yl)ethanol and some related compounds

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19882731 ◽

1988 ◽

Vol 53 (11) ◽

pp. 2731-2741 ◽

Cited By ~ 2

Author(s):

Jiří Jílek ◽

Martin Valchář ◽

Jiří Holubek ◽

Nataša Dlohožková ◽

Josef Pomykáček ◽

...

Keyword(s):

Preclinical Studies ◽

Acid Chlorides ◽

Substitution Reactions ◽

Related Compounds

10-(2-Bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepin (X), prepared by two methods, was subjected to substitution reactions with 2-(1-piperazinyl)ethanol, 3-(1-piperazinyl)propanol, 1-methylpiperazine, 3-(1-piperazinyl)propionamide, piperazine, and 1-(ethoxycarbonyl)piperazine and gave the title compounds II-VII. The alcohol II was esterified by treatment with acid chlorides to compounds VIII and IX. Compounds II, V, and VIII proved to be noncataleptic neuroleptic agents and II (clopithepin, VÚFB-17 076) was selected for preclinical studies.

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Substituted N,N-Dimethyl-3-(phenylthio)- and -4-(phenylthio)benzylamines

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19920194 ◽

1992 ◽

Vol 57 (1) ◽

pp. 194-203 ◽

Cited By ~ 5

Author(s):

Karel Šindelář ◽

Vojtěch Kmoníček ◽

Marta Hrubantová ◽

Zdeněk Polívka

Keyword(s):

Serotonin Receptors ◽

Hydrobromic Acid ◽

Antidepressant Activity ◽

Benzoic Acids ◽

Lithium Aluminium Hydride ◽

Acid Chlorides ◽

Activity Inhibition ◽

Lithium Aluminium ◽

The Brain

(Arylthio)benzoic acids IIa - IIe and VIb - VId were transformed via the acid chlorides to the N,N-dimethylamides which were reduced either with diborane "in situ" or with lithium aluminium hydride to N,N-dimethyl-(arylthio)benzylamines Ia - Ie and Vb - Vd. Leuckart reaction of the aldehydes IX and X with dimethylformamide and formic acid afforded directly the amines Va and Ve. Demethylation of the methoxy compounds Ia and Ve with hydrobromic acid resulted in the phenolic amines If and Vf. The most interesting N,N-dimethyl-4-(phenylthio)benzylamine (Va) hydrochloride showed affinity to cholinergic and 5-HT2 serotonin receptors in the rat brain and some properties considered indicative of antidepressant activity (inhibition of serotonin re-uptake in the brain and potentiation of yohimbine toxicity in mice).

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