Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 2-Fluoro-8-substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

1982 ◽  
Vol 47 (11) ◽  
pp. 3114-3133 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Miroslav Ryska ◽  
Antonín Dlabač ◽  
...  
Keyword(s):  
Sodium Hydroxide ◽  
Sodium Hydride ◽  
Central Ring ◽  
Highly Active ◽  
Psychotropic Agents ◽  
Triethylbenzylammonium Chloride ◽  
Depot Neuroleptic ◽  
Boron Tribromide ◽  
Long Acting ◽  
By Products

The aldehydes VIa and VIb were transformed by treatment with chloroform and sodium hydroxide in the presence of triethylbenzylammonium chloride to the α-chloro acids VIIa and VIIb which were demethylated with boron tribromide and the products were cyclized with sodium hydroxide in dimethyl sulfoxide to 2-fluoro-6H-dibenz[b,e]-1,4-oxathiepin-6-carboxylic acids Ia and Ib. Syntheses of the aldehydes XVIIbcd were carried out and the products treated with 1-methyl-4-piperidylmagnesium chloride to give the amino alcohols XVIbcd. Cyclizations with sodium hydride in dimethylformamide afforded the title compounds XIIbcd; compounds XVIIIbc and XIX were isolated as by-products and characterized. Compound XIIb was transformed via the secondary amine XIIIb to the amino alcohol XIVb which was esterified to the decanoate XVb. Substances XIIbcd are highly active neuroleptic agents with an important prolongation of the central depressant effect. The decanoate XVb revealed the properties of a medium long acting depot neuroleptic.

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Synthesis of 6-(aminoalkyl) derivatives of 6H-dibenz[b,e]-1,4-oxathiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1367-1381 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Miroslav Ryska ◽  
Antonín Dlabač ◽  
...  
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Hydroxide ◽  
Benzyl Bromide ◽  
Sodium Hydride ◽  
Aqueous Sodium Hydroxide ◽  
Aqueous Sodium ◽  
Psychotropic Agents ◽  
Triethylbenzylammonium Chloride ◽  
Boron Tribromide ◽  
Derivatives Of

Heating of 2-(2-hydroxyphenylthio)benzoic acid (XX) with acetic anhydride gave dibenz[b,e]-1,4-oxathiepin-6-one (XXII). Demethylation of 2-(2-methoxyphenylthio)benzyl bromide (XI) with boron tribromide and the following treatment with aqueous sodium hydroxide in dimethyl sulfoxide afforded 6H-dibenz[b,e]-1,4-oxathiepin (I) which was halogenated with chlorine or N-bromosuccinimide only to the undesirable 2-halogeno derivatives II and III. A reaction of 2-(2-methoxyphenylthio)benzaldehyde (XII) with chloroform and 50% aqueous sodium hydroxide in the presence of triethylbenzylammonium chloride led to the α-chloro acid XIX whose demethylation with boron tribromide and the following cyclization with sodium hydroxide in dimethyl sulfoxide gave a mixture with prevailing 6H-dibenz[b,e]-1,4-oxathiepin-6-carboxylic acid (IV). Amino alcohols XXV-XXVIII were obtained by reactions of 2-(2-fluorophenylthio)benzaldehyde (XXIV) with the corresponding Grignard reagents and the products were cyclized with sodium hydride in dimethylformamide to the title compounds V-VIII. While compounds V and VI showed antireserpine effects and can be considered as potential antidepresants, compound VIII has a strong central depressant activity, brings about ataxia, hypothermia and potentiates the cataleptic action of neuroleptics (properties of a tranquillizer).

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

1982 ◽  
Vol 47 (11) ◽  
pp. 3077-3093 ◽  
Author(s):  
Karel Šindelář ◽  
Jiřina Metyšová ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Protiva ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Amino Alcohol ◽  
Sodium Hydride ◽  
Amino Alcohols ◽  
Central Ring ◽  
Psychotropic Agents ◽  
High Degree ◽  
By Products ◽  
Antiapomorphine Effect ◽  
Central Depressant

2-(2-Fluorophenylthio)benzaldehydes IXa-c and 5-chloro-2-(2-fluorophenylthio)acetophenone were treated with 1-methyl-4-piperidylmagnesium chloride and 3-dimethylaminopropylmagnesium chloride, respectively, and the resulting amino alcohols VIa-c, XVII and XVIII were cyclized with sodium hydride in dimethylformamide. In addition to the title compounds Ia-c, XIX and XX, several types of by-products were obtained. Demethylation of compound Ib by the chloroformate method afforded the secondary amine IIb which was transformed to the amino alcohols IIIb and Vb. Compounds Ia-c are very potent neuroleptics with a high degree of central depressant and cataleptic activity. The amino alcohol Vb exhibits a very strong antiapomorphine effect in rats.

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Derivatives of 11H-dibenz[b,f]-1,4-oxathiepin

1982 ◽  
Vol 47 (3) ◽  
pp. 967-983 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Antonín Dlabač ◽  
Jiřina Metyšová ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Sodium Hydride ◽  
Sulfuryl Chloride ◽  
Side Chains ◽  
Central Ring ◽  
Lithium Compounds ◽  
Psychotropic Agents ◽  
Trifluoromethyl Derivative ◽  
Derivatives Of

Reactions of 2-bromobenzyl bromide and its analogues XVII and XXV with 2-hydroxythiophenol resulted in 11H-dibenz[b,f]-1,4-oxathiepin (Ia) and its 2-chloro (Ib) and 2-trifluoromethyl derivative (IC). Treatment of the lithium compounds derived from Ia and Ib with carbon dioxide and dimethylaminoalkyl chlorides gave compounds IIa, Va and VIab; modification of side chains led to amines IVa, VIIa and VIIIa. 11-(1-Methyl-4-piperidyl) derivatives Xbc were obtained by chlorination of compounds Ibc with sulfuryl chloride or N-chlorosuccinimide and the following treatment with 1-methyl-4-piperidylmagnesium chloride. Compound Ib was transformed by oxidation to the sulfone XX affording by treatment with sodium hydride and tert-aminoalkylchlorides the basic sulfones XXI and XXII. While the nuclearly unsubstituted amines with the aliphatic side chains (IVa and VIIa) have intensive antireserpine activity and are potential antidepressants, the 11-(1-methyl-4-piperidyl) derivatives with a substituent in position 2 of the skeleton (Xbc) are potential neuroleptics; the trifluoromethyl derivative Xc especially has outstanding cataleptic and antiapomorphine efficacy.

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Synthesis of 11-(dimethylaminoalkyl) derivatives of 11H-dibenzo[b,e]-1,4-dioxepin and 11H-dibenzo[b,e]-1,4-dithiepin

1982 ◽  
Vol 47 (1) ◽  
pp. 72-87 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Emil Svátek ◽  
Antonín Dlabač ◽  
...  
Keyword(s):  
Liquid Ammonia ◽  
Sodium Hydride ◽  
Central Ring ◽  
Simultaneous Formation ◽  
Alternative Synthesis ◽  
Psychotropic Agents ◽  
Reserpine Hypothermia ◽  
The One ◽  
High Degree ◽  
Derivatives Of

1-[2-(2-Fluorophenoxy)phenyl]-4-dimethylaminobutanol (XI) was synthesized from 2-(2-fluorophenoxy)benzoic acid (VIII) in three steps and cyclized with sodium hydride in dimethylformamide to the title compound V. Reaction of 5-chloro-2-(methylthio)thiophenol (XIV) with sodium and liquid ammonia afforded benzene-1,2-dithiol (XIII) which was treated with 2-bromobenzyl bromide and gave 11H-dibenzo[b,e]-1,4-dithiepin (II). An alternative synthesis of compound II consisted in the cyclization of 2-(2-bromophenylthiomethyl)thiophenol (XVIII) and was accompanied by the simultaneous formation of 6H, 12H-dibenzo[b,f]-1,5-dithiocin (XIX) and thianthrene (XX). Reaction of compound II with n-butyllithium and the following treatment with dimethylaminoalkyl chlorides or with carbon dioxide resulted on the one hand in two further title compounds VI and VII, and in the carboxylic acid XXI on the other. 2-Chloro-11H-dibenzo[b,e]-1,4-dithiepin (XXII) was obtained by a further synthesis alternative using in the first step the cyclization of 2-(4-chloro-2-chloromethylphenylthio)thiophenol (XXV). Compound VI and VII showed a high degree of activity in the test of antagonization of reserpine hypothermia in mice.

On-site sodium metal production with electrolysis by offshore wind or solar cell power generation for hydrogen generation

2009 ◽  
Vol 1216 ◽  
Author(s):  
Masataka Murahara ◽  
Kazuichi Seki ◽  
Yuji Sato ◽  
Etsuo Fujiwara
Keyword(s):  
Power Generation ◽  
Solar Cell ◽  
Sodium Hydroxide ◽  
Hydrogen Generation ◽  
Raw Material ◽  
Offshore Wind ◽  
Hydrogen Storage Material ◽  
Metal Production ◽  
Sodium Metal ◽  
By Products

AbstractSodium metal reacts with water explosively to generate hydrogen. Therefore, sodium metal can have an important role as a hydrogen storage material. Seawater contains water most and sodium second. Seawater is electrolyzed by offshore wind or solar cell power generation to produce sodium; which is transported to a thermoelectric power plant on land and then is reacted with water to produce hydrogen for electric power generation. Sodium hydroxide, a by-product, is used as a raw material for soda industries. In the sodium production process, many by-products such as fresh water, magnesium, sodium hydroxide, hydrochloric acid, and sulfuric acid are produced. Thus, sodium metal is an economical, renewable, and sustainable fuel that discharges neither CO2 nor radioactivity.

Phosphanchalkogenide und ihre Metallkomplexe. IV. Halogenierungsprodukte der Gold(I)halogenidkomplexe einiger Diphosphanmonochalkogenide

2016 ◽  
Vol 71 (3) ◽  
pp. 249-265 ◽  
Author(s):  
Christina Taouss ◽  
Peter G. Jones
Keyword(s):  
Membered Ring ◽  
Quantitative Yield ◽  
X Ray Diffraction ◽  
Central Ring ◽  
X Ray ◽  
Hydrolysis Products ◽  
Related Product ◽  
Hydrolysis Of ◽  
By Products

AbstractDiphosphanegold(I) complexes of the form dppmEAuX [dppm = bis(diphenylphosphano)methane, E = S, Se; X = Br, I], dppeEAuX [dppe = 1,2-bis(diphenylphosphano)ethane; E = O, S; X = Br, I] and dppbzEAuX [dppbz = 1,2-bis(diphenylphosphano)benzene; E = S, Se, X = Br, I] were treated with elemental X2. With dppm, the three products [dppmEAuX2]+X3– (E = S, X = Br (1), I (2); E = Se, X = I (3) were obtained in quantitative yield. These are gold(III) complexes involving a five-membered ring . With dppe, the only related product was [dppeEAuBr2]+Br3– (4), in which the central ring is six-membered with two carbon atoms. These dppe systems are very sensitive to oxidation/hydrolysis of the ligand, and several such unintended products were isolated and identified. The reaction of dppbzSAuBr with bromine leads to [dppbzS]2+[AuBr4]–Br– (5), the dication of which is formally 1,1,3,3-tetraphenylbenzo[d]-2-thia-1, 3-diphosphol-1,3-diium and contains a central five-membered ring . The dications are associated with the bromide anions via S…Br contacts of ca. 3.1 Å to form inversion-symmetric S2Br2 rings. The halogenation of the dppbzSe derivatives leads to loss of selenium and formation of dppbzAuBr3 (6), with [4+1] coordination at gold, or the known compound [dppbzAuI2]+I3– (7). All products 1–6 were subjected to X-ray diffraction analyses, as were four hydrolysis products 4a–d and two further by-products [5(thtBr+)·2Br3–·3(AuBr4–)] (1a) and (tht)AuBr3 (1b). Compound 1a displays unusually short Br…Br contacts of 3.2398(8) Å between neighbouring tetrabromidoaurate(III) ions.

scholarly journals Mechanical Properties of Geopolymer Concrete with Flyash and Metakaolin

2019 ◽  
Vol 9 (1) ◽  
pp. 3863-3868 ◽  
Keyword(s):  
Mechanical Properties ◽  
Fly Ash ◽  
Sodium Hydroxide ◽  
Silica Content ◽  
Geopolymer Concrete ◽  
Long Term Effects ◽  
Concrete Production ◽  
High Silica ◽  
By Products

Trials has been made to produce efficient GPC which gives maximum strength. By-Products from industries such as Fly-Ash, Metakaolin and GGBS can be used in concrete replacement which in-turn reduces carbon-di-oxide (CO2 ) emission affecting to green house. Using the above said products also leads to reduction of water demand in concrete and also shows comparatively no effects on long term effects in concrete, these by-products can effectively be used in concrete production. The high silica content in Fly-Ash and Metakaolin increases the bonding in concrete which in-turn increases the mechanical properties of concrete. Geopolymer concrete of M50 grade was proposed to be produced using fly-ash and Metakaolin instead of cement.Alklai solutions Sodium Hydroxide (NaOH), Sodium Silicate (Na2SiO3) were replaced with water for better bonding and mixing. Molarity of Sodium Hydroxide with 10M and 12M was considered for this study. Ratio of Alkaline solution were considered as 1:2,1:2.5&1:3 to determine the optimum ratio which gives effective strength. In this experimental study, tests were carried on concrete specimens with percentage replacement of Fly-Ash with Buff Metakaolin in variable percentages of 20,40,60,80&100. Mechanical properties of concrete specimens were studied and were compared with control mix results.

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