Big Chemical Encyclopedia

Chemical substances, components, reactions, process design ...

Articles Figures Tables About

Thioxanthenes

Thioxanthenes.—The method of synthesizing xanthones that was mentioned in the previous section has also been applied to the corresponding thioxanthones. A compound which was described as 9,10-diphenyl-10-thia-anthracene has been shown to contain mono-, di, and tri-phenylthioxanthene.  [Pg.319]

Deuterium labelling and n.m.r. spectroscopy have been used to study the conformation of thioxanthenium methylides which exist in the e conformation.The stereochemistry (including conformation) of 9-(aryl)thioxanthene 10-oxides and 10,10-dioxides has also been investigated. [Pg.319]

Kataoka, H. Shimizu, Y. Itagaki, and T. Higuchi, Tetrahedron Lett., 1979, 1603. [Pg.319]

Reduction with zinc dust in aqueous sulfuric acid gives 2-methyl-4-aminothiophenol (28) Condensation with 2-chlorobenzoic acid (Ullmann reaction) leads to 29, which can close to but one thiox-anthone (25) on treatment with sulfuric acid. Although this procedure is longer than the original, the yields are good and the sequence is regioselective.  [Pg.398]

It was subsequently discovered that lucanthone is metabolized in the body in part to hycanthone (30), a compound with enhanced schistomacidal activity. The relatively high biologic activity of lucanthone in experimental animals compared to man was subsequently attributed to the inefficient hydroxylating system present in man for this biochemical conversion.Microbiologic oxidation of lucanthone by fermentation with the fungus Aspergil-lus scelorotium affords hycanthone.  [Pg.398]

The efficacy of the phenothiazines for the treatment of various psychoses led to extensive synthetic programs aimed at modulation of the biologic spectrum of these molecules. As seen elsewhere, much of this work has centered on changes of the nature of the atoms that constitute the center ring. Thus, for example, it has proven possible to replace the nitrogen atom of the phenothiazine by carbon while maintaining neuroleptic activity. [Pg.399]

Ullmann condensation of the sodium salt of p-chlorothiophe-nol (31) with 2-iodobenzoic (32) acid gives 33. Cyclization by means of sulfuric acid affords the thioxanthone, 34. Reaction with the Grignard reagent from 3-dimethylaminopropyl chloride affords the tertiary carbinol (35). Dehydration by means of acetic anhydride affords chlorprothixene as a mixture of geometric isomers, 36. (Subsequent work showed the Z isomer-chlorine and amine on the same side—to be the more potent compound.) Chlorprothixene is said to cause less sedation than the phenothiazines.  [Pg.399]

Appropriate modification of the last few steps affords clo-penthixol (37). It is of note that this compound approaches the potency of one of the most active phenothiazines, perphenazine, an agent that has a very similar side chain. [Pg.399]


Alkylated sulfonamide groups have proven useful additions to the phenothiazine nucleus. The same seems to hold true in the thioxanthene series. Chlorosulfonation of the benzoic acid, 38, followed by displacement with dimethylamine affords the sulfonamide, 39. This is then taken on to the substituted thioxanthone (41) by the sequence of steps shown above Grignard condensation followed by dehydration gives thiothixine (42). [Pg.400]

Reduction of the exocyclic double bond generally decreases neuroleptic activity in this series. Some of these compounds, however, show other activities. Methixene (44), for example, is used as an antispasmodic agent. It is prepared by alkylation of the sodium salt of thioxanthene (43) with w-methyl-3-chloromethyl-piperidine. ... [Pg.400]

Chemical Name 3-(2-chloro-9H-thioxanthen-9-vlidene)-N,N-dimethyl-1-propanamine... [Pg.325]

Trans-2-chloro-9-(aj-dimethylamino-propylidene)-thioxanthene [MP 98°C, MP of the hydrochloride 225°C (corr.)], is a valuable medicinal agent, being used as a tranquilizer and antiemetic agent, whereas the corresponding cis isomer (MP 44°C, MP of the hydrochloride 209°C) is not useful for these indications, as described in U.S. Patent 3,115,502, which describes procedures for conversion of the cis to the trans form. [Pg.326]

Chemical Name 4-[3-(2-Chloro-9H-thioxanthen-9-ylidene)propyl] -1-piperazineethanol Common Name —... [Pg.374]

Chemical Name 4-[3- [2-(trifluoromethyl)-9H-thioxanthen-9-ylidenel propyl] -1-piperazine-ethanol... [Pg.680]

Chemical Name 1-methyl-3-(9H-thioxanthen-9-yl-methyl)piperidine hydrochloride Common Name —... [Pg.979]

The aqueous hydrochloric solution is made alkaline by adding dilute sodium hydroxide, and the thioxanthene base is isolated by extraction with ether. This results in 22 g of a slightly yellow, viscous base of BP 171° to 175°C/0.07 mm. [Pg.980]

Chemical Name (Z)-N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene] thioxanthene-2-sulfonamide... [Pg.1471]

Thioxanthene Thionyl chloride n-Butyllithium Pa raformaldehyde Sodium borohydride... [Pg.1472]

Dimethy/su/famy/thioxanthene To a slurry of dry sodium thioxanthene-2-sulfonate (33.3 grams, 0.111 mol) in 50 ml of N,N-dimethylformamide was added thionyl chloride (14.3 grams, 0.122 mol) in divided portions. An exothermic reaction ensued with complete dissolution being effected in minutes. Treatment of the reaction mixture with crushed ice precipitated a gum which crystallized after a short period of stirring. The sulfonyl chloride was filtered, washed with water, and stirred with 100 ml of liquid dimethylamine. [Pg.1472]

Substituted dibenzo[6,/]thiepins can be generated from thioxanthene derivatives by the rearrangement of carbocation 1. Compared with other possible cations, the tropylium ion type 1C is favored because of its resonance energy. Depending on the reaction conditions, the thiepin cation can react to give thiepins by loss of a proton, or by trapping a nucleophile, followed by elimination. [Pg.86]

Lithiation of thioxanthene by butyllithium and condensation with formaldehyde gives thioxanthene-9-methanol. The p-toluenesulfonyl derivative 2, on treatment with refluxing formic acid, rearranges to a dibenzotropylium ion, which gives the elimination product 3 in 44% yield.20... [Pg.86]

The thioxanthene ligand is oxidized to thioxanthone and sulfone ligands, the ratio of which depends on the amount of KMn04 Eq. (37) ... [Pg.87]

Ternay and coworkers examined the conformations of thioxanthene-10-oxide (186) and related compounds. They found that oxygen preferred the pseudoequatorial position, 186e, but that the amount of pseudoaxial conformer, 186a, increased when the oxygen was complexed with iodine monochloride or trifluoroacetic acid171. [Pg.88]

Table 3 presents the hyperfme splitting constants of some sulfur-containing aromatic radical anions. The series studied included the monoxides and dioxides of dibenzothio-phene 1, thioxanthene 2, thioxanthone 3, dibenzo[b,/] thiepin 4 and dithienothiophene dioxide 5. [Pg.1050]

The ESR spectrum of the thioxanthene S, S-dioxide radical anion itself shows that the two possible conformers coexist, since the two methylene protons are not equivalent. In the case of the 9-monoalkyl derivatives, the large coupling constant observed for the 9-proton leads to the conclusion that the 9-substituent is in the boat equatorial position as in II1 F Thus the radical anions and the neutral molecule display different conformations. The protons in the 9-position of the radical anions of cis-9-methylthioxanthene S-oxides (2, n — 1, R1 = H, R2 = CH3) have an appreciable coupling constant10 which suggests that these radical anions have the substituent in the pseudo-axial position. Furthermore, in the radical anions the S—O bond is pseudo-axial. These situations are exactly the opposite of that observed for the neutral compound. [Pg.1051]

CN (Z)-3-(2-chloro-9f/-thioxanthen-9-ylidene)-M(V-ciimethyl-l-propanamine hydmhloride... [Pg.447]

CN 4-[3-[2-(trifluoromethyl)-9//-thioxanthen-9-ylidene]propyl]-l-piperazineethanol dihydrochloride... [Pg.903]


See other pages where Thioxanthenes is mentioned: [Pg.217]    [Pg.235]    [Pg.359]    [Pg.368]    [Pg.369]    [Pg.92]    [Pg.93]    [Pg.397]    [Pg.399]    [Pg.401]    [Pg.979]    [Pg.1472]    [Pg.1199]    [Pg.1199]    [Pg.1503]    [Pg.563]    [Pg.704]    [Pg.1051]    [Pg.1209]    [Pg.378]    [Pg.378]    [Pg.465]    [Pg.965]    [Pg.524]    [Pg.1311]    [Pg.2052]    [Pg.2307]    [Pg.2361]   
See also in sourсe #XX -- [ Pg.353 ]

See also in sourсe #XX -- [ Pg.272 , Pg.295 ]

See also in sourсe #XX -- [ Pg.236 , Pg.238 ]

See also in sourсe #XX -- [ Pg.347 , Pg.675 ]

See also in sourсe #XX -- [ Pg.281 ]

See also in sourсe #XX -- [ Pg.127 ]

See also in sourсe #XX -- [ Pg.297 , Pg.300 ]

See also in sourсe #XX -- [ Pg.260 , Pg.264 ]

See also in sourсe #XX -- [ Pg.683 ]

See also in sourсe #XX -- [ Pg.19 ]

See also in sourсe #XX -- [ Pg.186 , Pg.187 ]

See also in sourсe #XX -- [ Pg.262 , Pg.262 , Pg.263 ]




SEARCH



10-Thioxanthene-9-thione

Antagonist thioxanthenes

Antipsychotic drugs thioxanthene

Dopamine antagonists Thioxanthenes

Levodopa Thioxanthenes

Neuroleptics thioxanthene

Thioxanthen-9-ones

Thioxanthene

Thioxanthene

Thioxanthene Thiothixene

Thioxanthene antipsychotics

Thioxanthene derivatives

Thioxanthene oxide

Thioxanthenes Antipsychotic drugs

Thioxanthenes and Thioxanthones

Thioxanthenes, Thioxanthones, and Related Compounds

© 2024 chempedia.info