Synthesis of 3-chloro-5-(4-methylpiperazino)-6,7-dihydro-5H-dibenzo[b,g]thiocin, an eight-membered ring homologue of the neuroleptic agent octoclothepin

1980 ◽  
Vol 45 (2) ◽  
pp. 491-503 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Miroslav Protiva
Keyword(s):  
Propionic Acid ◽  
Title Compound ◽  
Benzyl Chloride ◽  
Sodium Hydride ◽  
Diethyl Malonate ◽  
Membered Ring ◽  
Aluminium Chloride ◽  
Phenyl Propionic Acid ◽  
Neuroleptic Agent ◽  
Central Depressant

Alkylation of diethyl malonate with 2-(4-chlorophenylthio)benzyl chloride, the following hydrolysis and decarboxylation gave 3-[2-(4-chlorophenylthio)phenyl]propionic acid (IV); its chloride was cyclized in low yield by treatment with aluminium chloride to 4-(4-chlorophenylthio)indanone (V). The corresponding methylpiperazine derivative VIII was prepared viaintermediates VI and VII. A reaction of 3-(2-mercaptophenyl)propionic acid with 5-chloro-2-iodobenzoic acid and the following esterification resulted in the diester XVI which was cyclized by a Dieckmann reaction using sodium hydride in toluene to give ethyl 3-chloro-5-hydroxy-7H-dibenzo[b,g]thiocin-6-carboxylate (XVII). The acid hydrolysis afforded the ketone XVIII which was transformed via the intermediates XX and XXI to the title compound II. The product has a mild central depressant activity but it lacks the character of a neuroleptic agent.

β-ANTHRONYL-β-PHENYL-PROPIONIC ACID AND ITS DERIVATIVES SYNTHESIS OF THE γ-ANTHRONYL-α-HYDRINDONE

1933 ◽  
Vol 8 (6) ◽  
pp. 600-615 ◽  
Author(s):  
Paul E. Gagnon ◽  
Lucien Gravel
Keyword(s):  
Propionic Acid ◽  
Malonic Acid ◽  
Diethyl Malonate ◽  
Phosphorus Pentachloride ◽  
Alcoholic Solution ◽  
Ethyl Esters ◽  
Aluminium Chloride ◽  
Tautomeric Forms ◽  
Phenyl Propionic Acid ◽  
Propionyl Chloride

Benzaldehyde and o-chlorbenzaldehyde were readily condensed with ethyl and methyl malonate, giving rise to unsaturated esters. The esters were condensed with anthrone in alcoholic solution in the presence of piperidine. Hydrolysis of the product with sulphuric acid yielded β-anthronyl-β-phenyl-propionic acid. The chloride of this acid was formed by the action of phosphorus pentachloride. Two tautomeric derivatives of γ-anthronyl-α-hydrindone result from the action of aluminium chloride on β-anthronyl-β-phenyl-propionyl chloride. No benzanthrone derivatives were formed.The action of bromine on the two tautomeric forms of γ-anthronyl-α-hydrindone gave rise to one monobromide only, and oxidation of the two tautomers yielded only anthraquinone and phthalic acid.The method of preparation of β-anthronyl-β-phenylpropionic acid has been improved and the following compounds have been described, as far as the authors are aware, for the first time: the dimethyl and diethyl esters of o-chlor-benzylidene - malonic acid and anthrone - o - chlorbenzylidene - malonic acid; anthrone - benzylidene - diethyl - malonate; β-anthronyl - β- (o - chlorphenyl) - propionic acid; the silver salt, chloride, amide, anilide, methyl and ethyl esters of β-anthronyl-β-phenyl-propionic acid; γ-anthronyl-α-hydrindone (enolic and ketonic forms); γ-anthronyl-β-brom-α-hydrindone; and the hydrazone hydrate, phenylhydrazone, oxime and semicarbazone of γ-anthronyl-α-hydrindone.

An Elegant Synthetic Route to 3-Cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles

2004 ◽  
Vol 59 (1) ◽  
pp. 106-108 ◽  
Author(s):  
Isravel A. Danish ◽  
Karnam J. R. Prasad
Keyword(s):  
Elemental Analysis ◽  
Spectral Methods ◽  
Title Compound ◽  
Sodium Hydride ◽  
Synthetic Route ◽  
Mass Spectral ◽  
Plausible Mechanism

Abstract 2-Benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazoles (1a - e) obtained from the corresponding 1- oxo-1,2,3,4-tetrahydrocarbazoles on reaction with malononitrile in dry benzene with sodium hydride afforded 3-cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles (2a - e) in good yields. A plausible mechanism for the formation of the title compound has been proposed and all the compounds were characterised by IR, NMR, mass spectral methods and elemental analysis.

scholarly journals Insights into the interactions and dynamics of a DES formed by phenyl propionic acid and choline chloride

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Parisa Jahanbakhsh Bonab ◽  
Alireza Rastkar Ebrahimzadeh ◽  
Jaber Jahanbin Sardroodi
Keyword(s):  
Diffusion Coefficient ◽  
Liquid Phase ◽  
Propionic Acid ◽  
Structural Parameters ◽  
Choline Chloride ◽  
Self Diffusion ◽  
Phenyl Propionic Acid ◽  
Donor And Acceptor ◽  
Experimental Values ◽  
Self Diffusion Coefficient

AbstractDeep eutectic solvents (DESs) have received much attention in modern green chemistry as inexpensive and easy to handle analogous ionic liquids. This work employed molecular dynamics techniques to investigate the structure and dynamics of a DES system composed of choline chloride and phenyl propionic acid as a hydrogen bond donor and acceptor, respectively. Dynamical parameters such as mean square displacement, liquid phase self-diffusion coefficient and viscosity are calculated at the pressure of 0.1 MPa and temperatures 293, 321 and 400 K. The system size effect on the self-diffusion coefficient of DES species was also examined. Structural parameters such as liquid phase densities, hydrogen bonds, molecular dipole moment of species, and radial and spatial distribution functions (RDF and SDF) were investigated. The viscosity of the studied system was compared with the experimental values recently reported in the literature. A good agreement was observed between simulated and experimental values. The electrostatic and van der Waals nonbonding interaction energies between species were also evaluated and interpreted in terms of temperature. These investigations could play a vital role in the future development of these designer solvents.

scholarly journals 14,15-Didehydrohellebrigenin

2012 ◽  
Vol 68 (6) ◽  
pp. o1614-o1615
Author(s):  
Tong Yu ◽  
Hai-Yan Tian ◽  
Xiao-Feng Yuan ◽  
Shu-Zhi Hu ◽  
Ren-Wang Jiang
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Lactone Ring ◽  
Three Dimensional ◽  
Membered Ring ◽  
Envelope Conformation ◽  
Compound C ◽  
Dimensional Network ◽  
Hydroxy Groups

The title compound, C24H30O5, is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihydroxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclohexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclohexane rings A, B and C have normal chair conformations. The five-membered ring D with the C=C bond adopts an envelope conformation. Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is β-oriented at the C atom of ring D to which it is attached. There is an O—H...O hydrogen bond in the molecule involving the hydroxy groups. In the crystal, O—H...O hydrogen bonds link the molecules into chains propagating along [010]. The chains are linked by C—H...O contacts into a three-dimensional network.

Synthesis and structural investigation of 2-aminomethyl-3-(4-methoxy-phenyl)-propionic acid containing a peptide analogue of the amyloidogenic AS(6–7) sequence: inhibition of fibril formation

2017 ◽  
Vol 15 (19) ◽  
pp. 4218-4225 ◽  
Author(s):  
Arpita Paikar ◽  
Mintu Debnath ◽  
Debasish Podder ◽  
Supriya Sasmal ◽  
Debasish Haldar
Keyword(s):  
Amino Acid ◽  
Propionic Acid ◽  
Structural Investigation ◽  
Fibril Formation ◽  
Peptide Analogue ◽  
Phenyl Propionic Acid

The incorporation of a β-amino acid, namely 2-aminomethyl-3-(4-methoxy-phenyl)-propionic acid, inhibits amyloid-like fibril formation.

scholarly journals Preparation and Biological Activity of 2-(4-(Thiazol-2-yl)phenyl)propionic Acid Derivatives Inhibiting Cyclooxygenase.

1991 ◽  
Vol 39 (9) ◽  
pp. 2323-2332 ◽  
Author(s):  
Youichiro NAITO ◽  
Tomokazu GOTO ◽  
Fumihiko AKAHOSHI ◽  
Shiniciro ONO ◽  
Haruko YOSHITOMI ◽  
...  
Keyword(s):  
Biological Activity ◽  
Propionic Acid ◽  
Phenyl Propionic Acid

scholarly journals 2-Oxo-2H-chromen-7-yl 4-methylbenzoate

IUCrData ◽  
2018 ◽  
Vol 3 (7) ◽  
Author(s):  
Abdoulaye Djandé ◽  
Akoun Abou ◽  
Félix Kini ◽  
Konan René Kambo ◽  
Michel Giorgi
Keyword(s):  
Hydrogen Bond ◽  
Title Compound ◽  
Acute Angle ◽  
Membered Ring ◽  
Hirshfeld Surface ◽  
Supramolecular Interactions ◽  
Stacking Interactions ◽  
Weak Hydrogen Bond ◽  
Compound C ◽  
Benzene Rings

In the title compound, C17H12O4, the benzoate ring is oriented at an acute angle of 60.14 (13)° relative to the coumarin plane (r.m.s. deviation = 0.006 Å). This conformation is stabilized by an intramolecular C—H...O weak hydrogen bond, which forms a five-membered ring. Also present are π–π stacking interactions between neighbouring pyrone and benzene rings [centroid-to-centroid distances in the range 3.6286 (1)–3.6459 (1) Å] and C=O...π interactions [O...centroid distances in the range 3.2938 (1)–3.6132 (1) Å]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.

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