Neurotrope und psychotrope Substanzen II. Morphanthridin und Derivate. Neue Synthese des Propazepins

Jílek, J. O.; Pomykacek, J.; Svátek, E.; Seidlová, V.; Rajšner, M.; Pelz, K.; Hoch, B.; Protiva, M.

doi:10.1135/cccc19650445

Cited by 27 publications

(12 citation statements)

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“…An analytical sample melted at 120-121°C (ethanol). For C Zl H 22 CIFN z O z S (420'9) calculated: 59'92% C, 5'27% H, 6'66% N; found: 59'82% C, 5'24% H, 6'63% N.8-Chloro-3-f1uoro-1 0-piperazino-10, I1-dihydrodibenzo[b,fJthiepin (VI) A mixture of 23·1 g VII,16 g KOH and 20 ml ethanol was refluxed under stirring in a 120°C bath, diluted with 100 ml water and extracted with benzene. Processing of the extract yielded a crude base which was dissolved in 40 ml ethanol, the solution was neutralized with 7'0 g maleic acid; addition of 40 ml ether precipitated the maleate; 16·8 g (66%), m.p.…”

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confidence: 99%

Fluorinated tricyclic neuroleptics with prolonged effects: Some new 8-chloro-3-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins

Rajšner¹,

Svátek²,

Metyšová³

et al. 1977

Collect. Czech. Chem. Commun.

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Six new 8-chloro-3-fluoro-10-piperazino-lO,1l-dihydrodibenzo[b,f]thiepins II-VII were synthesized, amino alcohol II being a highly effective neuroleptic and tranquilizer in acute tests, dioxolane IV prolonging these effects upon oral administration. A new synthesis of acid VIII was developed, proceeding via (2-bromo-4-fluorophenyl)acetic acid (XI). A second geometric isomer of the 3--fluoro derivative of chloroprothixene (XIII) was prepared which, according to the IR spectrum, is of cis-configuration; it is inactive cataleptically and only a weak depressant. Acids XIVab were synthesized using selective bromination of phenylacetamide in the ortho-position. Starting from acid XIVa and via the intermediate XVIIa, 1-[2-(2-p-chlorophenylthiophenyl)-ethyl]-4-methylpiperazine (XIXa) was prepared, a new open model of octoclothepin which acted as an anticonvulsant and showed signs of antihistamine effects.In a previous communication! we described the synthesis of the 3-fluoro derivative of octoclothepin (I) which displayed a high degree of neuroleptic and depressant activity on oral application in acute tests and clear signs of prolongation of these effects. This was explained by a block of metabolic hydroxylation of the octoclothepin molecule by fluorination 1 ,2. The work has now been extended to include several analogues of I with modified N-substituents. Firstly, amino alcohol II was synthesized, this being a 3-fluoro derivative of the highly active noroxyclothepin 3 -5. It was prepared by a substitution reaction of 8, 1O-dichloro-3-fluoro-l 0, l1-dihydrodibenzo[b,f]-thiepinl with 1-(2-hydroxyethyl)piperazine. Its esterification with decanoyl chloride 6 (for method see 4 ) yielded the ester III which is a 3-fluoro derivative of the depot neuroleptic noroxyclothepin decanoate 4 ,7 ,8. Further prepared were IV and V with a 1,3-dioxolane or 4-methyl-l,3-dioxolane residue in the side chain; these are 3-fluoro derivatives of previously prepared octoclothepin analogues 9 which displayed, in comparison with octoclothepin, a much lower toxicity on oral administration. The purpose of synthesis of IV and V was to prepare oral neuroleptics with prolonged effect that would be less toxic than the 3-fluoro derivative of octoclothepin (I). ForPart CXIII in the series Neurotropic and Psychotropic Agents; Part CXI1: This Journal 42,2240 (1977).

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Fluorinated tricyclic neuroleptics with prolonged effects: Some new 8-chloro-3-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins

Rajšner¹,

Svátek²,

Metyšová³

et al. 1977

Collect. Czech. Chem. Commun.

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“…In den Tabellen wenden wir zur Bezeichnung der einzelnen pdiparativen Methoden die foIgenden Buchstabensymbole an: A Darstellung der chIorierten durch Reaktion, von 2-Jodbenzoesaure 4 oder ihrer Chlorderivate (II) mit Thiophenol oder seinem 2-ChIor-5 , 3-ChIor-6 oder 4-Chlorderivat 7 in KaIilaugelOsung bei Anwesenheit von Kupfer l , 3,7; B Reduktion der Sauren III mit Lithiumaluminiumhydrid in Ather oder Ather-Tetrahydrofuran-Mischung l ,3; C Dberfiihren der AIkohole VI in die Chloride VII durch Behandlung mit Thionylchlorid (gegebenenfalls in Gegenwart von Pyridin)l,3; D Substitutionsreaktion der Chloride VII mit Natriumcyanid in siedendem waBrigem Athanol l ,3; E Hydrolyse der Nitrile VIII zu den Siiuren IX mit siedender waBrig-alkoholischer Kalilauge l , 3 Bei der Synthese des l-Chlorderivats Ia (die Bedeutung der Symbole a-g geht aus den Tabellen I und II hervor) gingen wir von der neuen 6-Chlor-2-jodbenzoesaure (II, R = 6-CI) aus, die wir mittels Sandmeyer-Reaktion aus 6-Chlor-2-aminobenzoe_ saure 12 bereiteten, welche Verbindung aus 6-Chlor-2-nitrotoluoI 13 …”

Section: IIunclassified

Neurotrope und psychotrope Substanzen XXII. Weitere Chlorderivate des 10-(4-Methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepins und einige verwandte Stoffe

Pelz¹,

Ernest²,

Adlerová³

et al. 1968

Collect. Czech. Chem. Commun.

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Vnter Anwendung frUher beschriebener Methoden wurden sechs Ar-Monochlorderivate und das 2,8-Dichlorderivat des 10-(4-Methylpiperazino )-10, II-dihydrodibenzo[b, f]thiepins (/) synthetisiert. Ferner werden die entsprechenden 10-(2-Dimethylaminoathoxy)-Derivate XIV und drei weitere Amine dieser Gruppe (XV-XVII) beschrieben. In einigen Fallen wurden die Synthesen tiber neue Ausgangsstoffe durchgefiihrt (/1, XIX, XX); einige Nebenreaktionen (Bildung der Substanzen XVIII und XXI) werden beschrieben. Es wurde festgestellt, daB aIle beschriebenen Endprodukte eine schwachere zentral dampfende Wirkung aufweisen als die Grundsubstanz 1 (R 1 = R 2 = H) bzw. ihr 8-Chlorderivat (/, R 1 = H, R 2 = 8-CI).

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“…Using a modified synthesis of 1,4-dicarbonyl benzoine derivatives, 1,4-dicarbonyl compounds 2 were synthesized (Scheme 1) [11]. Reaction of ketones 1 [12] with chloroacetone in the presence of base in dimethyl sulfoxide (DMSO) resulted in formation of C-and O-alkylation products. Depending on the heteroatom in the seven membered ring, unexpected selectivity of C-vs. O-alkylation was observed for two pairs of compounds 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis Of 1,8‐dioxa‐dibenzo[e,h]azulenese

Pešić

Landek

Merćaep

et al. 2006

Journal of Heterocyclic Chem

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A novel synthetic route to 2‐methyl‐1,8‐dioxa‐dibenzo[e,h]azulenes [1] via cyclisation of the corresponding 1,4‐dicarbonyl compound is described. 1,4‐Dicarbonyl compounds were synthesized by the alkylation reaction of the 11H‐dibenzo[b,f]oxepine‐10‐one while analogous alkylation of 11H‐dibenzo[b,f]thiepine‐10‐one resulted in formation of O‐alkylated products. Selective oxidation of 2‐methyl group afforded 1,8‐dioxa‐dibenzo[e,h]azulenes with formyl and hydroxymethyl functionality at C(2) position.

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Neurotrope und psychotrope Substanzen II. Morphanthridin und Derivate. Neue Synthese des Propazepins

Cited by 27 publications

References 0 publications

Fluorinated tricyclic neuroleptics with prolonged effects: Some new 8-chloro-3-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins

Fluorinated tricyclic neuroleptics with prolonged effects: Some new 8-chloro-3-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins

Neurotrope und psychotrope Substanzen XXII. Weitere Chlorderivate des 10-(4-Methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepins und einige verwandte Stoffe

Synthesis Of 1,8‐dioxa‐dibenzo[e,h]azulenese

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