Synthesis of potential neuroleptics and tranquillizers: 2-(tert.Amino)-9-(3-dimethylaminopropylidene)thioxanthenes

1986 ◽  
Vol 51 (4) ◽  
pp. 937-947 ◽  
Author(s):  
Vojtěch Kmoníček ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Protiva

4-Dimethylamino-, 4-pyrrolidino-, 4-piperidino-, 4-morpholino- and 4-(4-methylpiperazino)-thiophenol (IIIa-IIIe), which were prepared by two methods and characterized as the 2,4-dinitrodiphenyl sulfides IVb-IVe, were transformed by treatment with 2-iodobenzoic acid and copper in aqueous potassium hydroxide to 2-(4-tert.aminophenylthio)benzoic acids (Va-Ve). Cyclization with polyphosphoric acid gave thioxanthones VIa-VIe which were treated with 3-dimethylaminopropylmagnesium chloride to give the diamino alcohols VIIa-VIId. VIIa, VIIc and VIId were dehydrated by heating with dilute sulfuric acid which resulted in mixtures of geometrical isomers of the olefinic bases Ia, Ic and Id. Crystallization of bases or salts led to homogeneous or almost homogeneous (Z)-isomers belonging to the active chlorprothixene series. The products are devoid of cataleptic and antiapomorphine activities and show only some properties of mild tranquillizers

1987 ◽  
Vol 52 (3) ◽  
pp. 793-803 ◽  
Author(s):  
Vojtěch Kmoníček ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiřina Metyšová ◽  
Miroslav Protiva

Reactions of (2-iodophenyl)acetic acid with 4-(dimethylamino)thiophenol, 4-piperidinothiophenol, and 4-morpholinothiophenol in boiling aqueous potassium hydroxide solutions in the presence of copper gave the arylacetic acids IVabc which were cyclized with polyphosphoric acid at 130 °C to 8-(tert.amino)dibenzo[b,f]thiepin-10(11H)-ones Vabc. The following reactions with 1-methylpiperazine in boiling benzene in the presence of titanium tetrachloride afforded the enamines IIabc. Compounds IIa and IIc were reduced with diborane to the 10,11-dihydro compounds Ia and Ic. Compound Ia (the 8-dimethylamino derivative of perathiepin) is a typical incisive neuroleptic agent with very strong cataleptic, antiapomorphine, central depressant, and antiadrenergic activities. The morpholino derivative Ic and the enamines IIb and IIc are less active.


1992 ◽  
Vol 57 (3) ◽  
pp. 439-445
Author(s):  
Magdy A. Wassel ◽  
Nalla K. Allahaverdova ◽  
Tofki G. Alkhazov

To determine the acidic and basic properties of the title catalysts, the adsorption of NH3 and SO2 was compared using pulse method. It was found that this characteristics undergoes changes when the Sn-Mo catalyst is treated with aqueous potassium hydroxide solutions of different concentrations. The catalyst treated with the more concentrated KOH solution possesses mainly properties of a base. When studying the oxidation of ethanol it has been found that the αCO2/αaldehyde conversion ratio increases with the time of contact of the mixture with the catalyst while the αCO2/α acid ratio is not affected. The study of two alcohols deuterated either in OH group (C2H5OD) or in the alkyl group ((C2D5OH) has shown that the substitution of C-H for C-D bond enhances the stability of the primary oxidation product, deuterated ethanal, so that it is not transformed further to acetic acid.


1969 ◽  
Vol 72 (11) ◽  
pp. 2436-2439 ◽  
Author(s):  
Yoshi KAMIYAMA ◽  
Koichiro GOTOH ◽  
Tatsuyoshi KOBAYASHI

2008 ◽  
Vol 42 (1) ◽  
pp. 84-91 ◽  
Author(s):  
Ignacio Ballesteros ◽  
Mercedes Ballesteros ◽  
Paloma Manzanares ◽  
M. José Negro ◽  
J. Miguel Oliva ◽  
...  

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