Synthetic studies on 5-(3,4-dimethoxyphenyl)-5,6-dihydrophenanthridin-6-ol,an analogue of perloline

1982 ◽  
Vol 35 (8) ◽  
pp. 1645 ◽  
Author(s):  
SI Clarke ◽  
RH Prager
Keyword(s):  
Title Compound ◽  
Polyphosphoric Acid ◽  
Hydrazoic Acid ◽  
Synthetic Studies

Two independent syntheses of the title compound (2), an analogue of perloline, are described. 9-(3,4-Dimethoxyphenyl)fluoren-9-ol reacted with hydrazoic acid in polyphosphoric acid to give 6-(3,4-dimethoxyphenyl)phenanthridine, the N-oxide of which was photolysed to 5-(3,4-dimethoxy-phenyl)phenanthridin-6-one (8) which was reduced to the title compound directly with sodium bis(2-methoxyethoxy)aluminium hydride ('Redal'), or by reduction to 5-(3,4-dimethoxypheny1)-5,6- dihydrophenanthridine followed by oxidation with N-bromosuccinimide. The phenanthridinone (8) was also synthesized by photolysis of the nitrone of 3,4-dimethoxy-N-fluorenylideneaniline.

Fluorinated analogues of tricyclic neuroleptics: 6,9-difluoro derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1980 ◽  
Vol 45 (10) ◽  
pp. 2688-2694 ◽  
Author(s):  
Irena Červená ◽  
Marta Hrubantová ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Title Compound ◽  
Substitution Reaction ◽  
Polyphosphoric Acid ◽  
Satisfactory Yield ◽  
Chloro Derivative ◽  
Cns Activity

The acid VI, obtained from 2,5-difluorothiophenol (IV) and (2-iodophenyl)acetic acid, afforded by cyclization with polyphosphoric acid 6,9-difluorodibenzo[b,f]thiepin-10(11H)-one (VII) in a satisfactory yield. Two further steps led to the chloro derivative X giving by a substitution reaction with 1-methylpiperazine the title compound III. This substance exhibits some 10% incoordinating activity of the unsubstituted compound I and an indication of cataleptic activity, in contrast to the inactive analogous dichloro compound II. The bulky atom of chlorine in the vicinity of the methylpiperazine residue interferes evidently with the CNS activity; the influence of the atom of fluorine is much less pronounced in this line.

Potential noncataleptic neuroleptic agents: 2,3-Dichloro-10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrobenzo[b,f]thiepin

1984 ◽  
Vol 49 (4) ◽  
pp. 992-1001 ◽  
Author(s):  
Jiří Urban ◽  
Antonín Dlabač ◽  
Martin Valchář ◽  
Miroslav Protiva
Keyword(s):  
Benzoic Acid ◽  
Potassium Carbonate ◽  
Title Compound ◽  
Substitution Reaction ◽  
Polyphosphoric Acid ◽  
Dopamine Metabolism ◽  
Nitro Derivative ◽  
High Dose ◽  
Chloro Derivative ◽  
Hydroxyethyl Piperazine

The 6-nitro derivative V, obtained by nitration of 3,4-dichlorobrombenzene, was transformed via the amine VI and nitrileVII to 2-bromo-4,5-dichlorobenzoic acid (IX). Its reaction with thiophenol in 3-methyl-1-butanol in the presence of potassium carbonate and catalytic amounts of copper and cuprous iodide afforded 4,5-dichloro-2-(phenylthio)benzoic acid (Xa) which was reduced to the alcohol XIa. The transformation to the homologous acid XIVa proceeded via noncharacterized intermediates XIIa and XIIIa. The cyclization with polyphosphoric acid at 150 °C resulted in 2,3-dichlorodibenzo[b,f]thiepin-10(11H)-one (XV) which was reduced to the alcohol XVI. Treatment with hydrogen chloride gave the unstable chloro derivative XVII whose substitution reaction with 1-(2-hydroxyethyl)piperazine led to the title compound II. Its dimethanesulfonate showed properties of a little toxic and noncataleptic tranquillizer. Because it does not influence the dopamine metabolism in rat brain in a rather high dose, it cannot be considered a neuroleptic.

A Simple Synthesis of Amphimedine

1991 ◽  
Vol 44 (2) ◽  
pp. 277 ◽  
Author(s):  
RH Prager ◽  
C Tsopelas ◽  
T Heisler
Keyword(s):  
Acid Treatment ◽  
Polyphosphoric Acid ◽  
Simple Synthesis ◽  
Hydrazoic Acid ◽  
Short Sequence ◽  
Marine Alkaloid ◽  
Alkaline Ferricyanide

The marine alkaloid amphimedine has been synthesized by a short sequence of reactions commencing from the known indenopyridinedione (2). Reaction with 4-pyridyllithium, followed by hydrazoic acid treatment, gave 5-(4-pyridyl)-3,6-phenanthrolin-4(3H)-one (12) which was converted into the chlorophenanthroline. The methyl-substituted fluorosulfonate salt of this compound was specifically oxidized by alkaline ferricyanide. Conversion of the pyridone into the nitrile gave the precursor which was cyclized to amphimedine by polyphosphoric acid.

scholarly journals 1-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methanamine

2018 ◽  
Author(s):  
Ganesh Shimoga ◽  
Eun-Jae Shin ◽  
Sang-Youn Kim
Keyword(s):  
1H Nmr ◽  
Title Compound ◽  
Polyphosphoric Acid ◽  
Mass Spectrometric ◽  
Ft Ir ◽  
Mass Spectrometric Techniques

1-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methanamine compound has been successfully synthesized by reacting p-Toluic hydrazide and glycine via polyphosphoric acid condensation route. The course of the reaction was found to be high yielding and the title compound was spectroscopically characterized by FT-IR, DSC, 13C/1H-NMR and Mass spectrometric techniques.

scholarly journals 1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine

Molbank ◽  
10.3390/m1014 ◽  
2018 ◽  
Vol 2018 (3) ◽  
pp. M1014
Author(s):  
Ganesh Shimoga ◽  
Eun-Jae Shin ◽  
Sang-Youn Kim
Keyword(s):  
1H Nmr ◽  
Title Compound ◽  
Polyphosphoric Acid

1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound was spectroscopically characterized by UV-Vis, FTIR, DSC, 13C/1H-NMR, and sass spectrometric techniques.

Fluorinated analogues of the tricyclic neuroleptics; 7-Fluoro and 7-trifluoromethyl derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1980 ◽  
Vol 45 (4) ◽  
pp. 1086-1098 ◽  
Author(s):  
Karel Šindelář ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Jiřina Metyšová ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Alkaline Hydrolysis ◽  
Title Compound ◽  
Polyphosphoric Acid ◽  
Titanium Tetrachloride ◽  
Keto Acid ◽  
Methanesulfonyl Chloride ◽  
Trifluoromethyl Derivative ◽  
By Products ◽  
Central Depressant

Reaction of 3-fluorothiophenol with (2-iodophenyl)acetic acid gave the acid VIII which was cyclized with polyphosphoric acid to the ketone XII. The first title compound VI was prepared via the intermediates XV and XVIII. Treatment of the ketone XII with 1-methylpiperazine in the presence of titanium tetrachloride resulted in the enamine XXIII. The similarly prepared acid IX was cyclized to the ketone XIII. By-products were the di-acid X and the enol-lactone XXIV, affording by alkaline hydrolysis the keto acid XXV. The synthesis of the second title compound VII was carried out from the ketone XIII via the intermediates XVI and XIX. 10,11-Dihydrodibenzo[b,f]thiepin-3,11-diol (XVII) gave by treatment with methanesulfonyl chloride and by the following reaction with 1-methylpiperazine the salt of 1-methylpiperazine with dibenzo[b,f]thiepin-3-ol (XXII) and 1-methyl-4-(methylsulfonyl)piperazine (XXVI)). Whereas the compound VI has low central depressant and cataleptic activity, the corresponding enamine XXIII is very potent in both lines. The trifluoromethyl derivative VII has the character of a neuroleptic but its depressant and cataleptic activity are ten times lower than those of the 8-trifluoromethyl isomer.

Synthetic studies toward inducamide C

2021 ◽  
Author(s):  
Ardalan A. Nabi ◽  
Lydia M. Scott ◽  
Daniel P. Furkert ◽  
Jonathan Sperry
Keyword(s):  
Natural Product ◽  
Structural Revision ◽  
Synthetic Studies

The rare benzoxazepine ring in the alkaloid inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary.

Crystal structure of 12H+-2,4-benzo-1,5-dioxa-8,12,16-triaza-cyclooctadec-2-ene-7,17-dione picrate

2002 ◽  
Vol 217 (1) ◽  
Author(s):  
G. Hundal ◽  
S. Kumar ◽  
M. S. Hundal ◽  
H. Singh
Keyword(s):  
Crystal Structure ◽  
Title Compound ◽  
Compound C

AbstractThe title compound [C

A neutron diffraction study of hydrogen bonding in the deuterium (hydrogen) L-arginine phosphate monohydrate

1997 ◽  
Vol 212 (3) ◽  
Author(s):  
Z. Cheng ◽  
Y. Cheng ◽  
L. Guo ◽  
D. Xu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Neutron Diffraction ◽  
Diffraction Study ◽  
Title Compound ◽  
Neutron Diffraction Study ◽  
Chemical Formula

AbstractThe crystal structure of the title compound D(H)LAP with chemical formula (D

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