New heterocycles derived from 2-aminothiophenol

1971 ◽  
Vol 24 (2) ◽  
pp. 405 ◽  
Author(s):  
JL Huppatz ◽  
RMJ Moore
Keyword(s):  
Dicarboxylic Acid ◽  
Spectral Data ◽  
Sulphuric Acid ◽  
Propionic Acid ◽  
Sodium Borohydride ◽  
Polyphosphoric Acid ◽  
Heterocyclic Ring ◽  
Phosphoryl Chloride ◽  
Alternative Synthesis ◽  
Derivatives Of

2-Aminothiophenol reacted with β-propiolactone in ethanol to give β-[o- (β-carboxyethylamino)phenylthio]propionic acid (1) which underwent cyclodehydration in polyphosphoric acid to give derivatives of two new heterocyclic ring systems, viz., 1,8-dioxo-1,2,3,4,5,6,7,8-octahydro-4- thia-5-azaphenanthrene (2) and 4,8-dioxo-3,4,7,8-tetrahydro-2H,6H- [1,4]thiazepino[2,3,4-ij]quinoline (3). Analytical and spectral data are presented which support the structures proposed for these compounds. ��� Alternative synthesis of each heterocycle was achieved by using media other than polyphosphoric acid to cyclize the dicarboxylic acid (1). Phosphoryl chloride gave β-(4-oxo-2,3,4,5-tetrahydro-1,5- benzothiazepin-5-yl)propionic acid (4), which was cylodehydrated smoothly to the thiazepine (3). Concentrated sulphuric acid afforded β- (4-oxo-1,2,3,4-tetrahydroquinol-8-ylthio)propionic acid (6) which was converted into the thiazaphenanthrene (2) by polyphosphoric acid. ��� Bromination reactions and reduction with sodium borohydride of the thiazepine (3) are also described.

scholarly journals SYNTHESIS AND REACTIONS OF 1-(4’-BROMOPHENACYL)-3-(4’-BROMO-PHENYL)-4,6-DIMETHOXYINDOLE

2010 ◽  
Vol 5 (2) ◽  
pp. 156-162
Author(s):  
Jumina Jumina
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Trifluoroacetic Acid ◽  
Boron Trifluoride ◽  
Polyphosphoric Acid ◽  
Glacial Acetic Acid ◽  
Boron Trifluoride Etherate ◽  
Phosphoryl Chloride ◽  
Acetyl Ester ◽  
Toluenesulfonic Acid

  1-Phenacyl-3-aryl-4,6-dimethoxyindoles 2b and 2c were obtained in good yields respectively through cyclization of N,N-diphenacylaniline 1b and 1c in trifluoroacetic acid. However, instead of giving pyrroloindole 3c, treatment of phenacylindole 2c with polyphosphoric acid afforded indolizine 5 in 42% yield. Phenacylindole 2c reacts with the Vilsmeier aroylation reagent consisted of a mixture of phosphoryl chloride and p-chloro-N,N-dimethylbenzamide to give 2-aroylindole 6 (32%) and pyrroloindole 7 (22%). When treated with sodium borohydride, phenacylindole 2c gave alcohol 8 in 83% yield. Nonetheless, treatment of alcohol 8 with either p-toluenesulfonic acid in glacial acetic acid or boron trifluoride etherate in benzene did not give the desired dihydropyrroloindole 12. Instead, the reactions afforded respectively acetyl ester 9 and indole 10 in 56% and 63% yield.   Keywords: phenacylindole, aroylindole, pyrroloindole, and indolizine.

scholarly journals Some New Derivatives of Organozirconium(IV) with Pyridinedicarboxylic Acids

2012 ◽  
Vol 9 (2) ◽  
pp. 744-748
Author(s):  
Satish C. Dixit ◽  
Rohit K. Singh
Keyword(s):  
Dicarboxylic Acid ◽  
Spectral Data ◽  
Magnetic Moment ◽  
Electrical Conductance ◽  
Pyridine Dicarboxylic Acid ◽  
Elemental Analyses ◽  
Stoichiometric Ratios ◽  
Derivatives Of ◽  
Pyridinedicarboxylic Acids

Reactions of dichlorobis(cyclopentadienyl)zirconium(IV) with pyridinedicarboxylic acidsviz. quinolinic acids (QAH2), 2,4-pyridine dicarboxylic acid (PAH2), isocinchomeronic acid (IAH2), cinchomeronic acid (CAH2) and dinicotinic acid (DAH2) were carried out in different stoichiometric ratios. Complexes of the type Cp2Zr(QAH)Cl, Cp2Zr(QAH)2, Cp2Zr(PAH)Cl, Cp2Zr(PAH)2, Cp2Zr(IAH)Cl, Cp2Zr(IAH)2, Cp2Zr(CAH)Cl, Cp2Zr(CAH)2, Cp2Zr(DAH)Cl and Cp2Zr(DAH)2were obtained. These new complexes were characterized on the basis of their elemental analyses, electrical conductance, magnetic moment and spectral data.

scholarly journals Pyridinedicarboxylic Acid Derivatives of Dichlorobis(cyclopentadienyl)titanium(IV)

2012 ◽  
Vol 9 (1) ◽  
pp. 277-281
Author(s):  
Satish C. Dixit ◽  
Rohit K. Singh
Keyword(s):  
Dicarboxylic Acid ◽  
Spectral Data ◽  
Quinolinic Acid ◽  
Magnetic Moment ◽  
Electrical Conductance ◽  
Dicarboxylic Acids ◽  
Pyridinedicarboxylic Acid ◽  
Pyridine Dicarboxylic Acid ◽  
Elemental Analyses ◽  
Derivatives Of

Reactions of dichlorobis(cyclopentadienyl)titanium(IV) with pyridine dicarboxylic acidsviz. quinolinic acid (QAH2), 2,4-pyridine dicarboxylic acid (PAH2), isocinchomeronic acid (IAH2), cinchomeronic acid (CAH2) and dinicotinic acid (DAH2) were carried out in different stoichiometric ratios. Complexes of the type Cp2Ti(QAH)Cl, Cp2Ti(QAH)2, Cp2Ti(PAH)Cl, Cp2Ti(PAH)2, Cp2Ti(IAH)Cl, Cp2Ti(IAH)2, Cp2Ti(CAH)Cl, Cp2Ti(CAH)2, Cp2Ti(DAH)Cl and Cp2Ti(DAH)2were obtained. These new complexes were characterized on the basis of their elemental analyses, electrical conductance, magnetic moment and spectral data.

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

A synthesis of alkylated 3-aminoisoquinolines and related compounds

1982 ◽  
Vol 35 (7) ◽  
pp. 1391 ◽  
Author(s):  
AJ Liepa
Keyword(s):  
Phosphoryl Chloride ◽  
Tertiary Amides ◽  
Derivatives Of ◽  
Related Compounds ◽  
Selection Of

N,N-Dialkyl derivatives of 3-aminoisoquinoline have been prepared by reaction of nitriles with various arylacetic acid tertiary amides in the presence of phosphoryl chloride. The synthesis has been extended to include a benzoisoquinoline and annulated isoquinolines by the selection of appropriate amide and nitrile precursors.

Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Amino Alcohols

1996 ◽  
Vol 61 (2) ◽  
pp. 288-297 ◽  
Author(s):  
Vladimír Pouzar ◽  
Ivan Černý
Keyword(s):  
Amino Acids ◽  
Hydroxy Group ◽  
Building Blocks ◽  
Amino Alcohols ◽  
New Approach ◽  
Alternative Synthesis ◽  
Oxime Derivatives ◽  
A Chain ◽  
Derivatives Of

New approach to the preparation of steroids with connecting bridge, based on an O-carboxymethyloxime (CMO) structure, and with terminal hydroxy group, is presented. 17-CMO derivatives of 3β-acetoxy- and 3β-methoxymethoxyandrost-5-en-17-one were condensed with α,ω-amino alcohols to give derivatives with a chain of seven to nine atoms. After THP-protection, these compounds were converted to 3-keto-4-ene derivatives. An alternative synthesis consisted in transformation of 17-CMO derivatives with bonded amino acids by reduction of the terminal carboxyl. The resulting compounds were designed as building blocks for the preparation of bis-haptens for sandwich immunoassays.

scholarly journals SYNTHESIS AND PRELIMINARY PHARMACOLOGICAL EVALUATION OF NEW NAPROXEN ANALOGUES HAVING 1, 2, 4-TRIAZOLE-3-THIOL

2017 ◽  
Vol 9 (7) ◽  
pp. 66
Author(s):  
Monther F. Mahdi ◽  
Noor H. Naser ◽  
Nethal H. Hammud
Keyword(s):  
Aromatic Aldehydes ◽  
Heterocyclic Ring ◽  
Inflammatory Activity ◽  
Control Group ◽  
Paw Edema ◽  
Dose Equivalent ◽  
Edema Model ◽  
Anti Inflammatory ◽  
Derivatives Of

Objective: The objective of this search was to synthesize a new naproxen analogues having a 1,2,4-triazole-3-thiol heterocyclic ring, and preliminary pharmacological assessment of the anti-inflammatory activity of the synthesized compounds. Methods: The synthesis of naproxen analogues that having 1,2,4-triazole-3-thiol heterocyclic ring occur through esterification of naproxen, and then its reaction with hydrazine hydrate, and carbon disulfide, finally different aromatic aldehydes reacted with triazole derivatives of naproxen containing amino group to produce schiff bases.Results: In vivo acute anti-inflammatory activity of the synthesize compounds (Va-Vd) was evaluated in rats using egg-white induced edema model of inflammation in a dose equivalent to (50 mg/kg) of naproxen. All tested compounds were produced a significant reduction in paw edema with respect to the effect of propylene glycol 50% v/v (control group). Compound Vd produced superior anti-inflammatory activity compared to naproxen.Conclusion: The results obtained in this work give evidence about the valid synthesis of 1,2,4 triazole-3-thiol derivatives of naproxen, which reacted with different aldehydes to yield several schiff bases. The incorporation of benzaldehyde possess para-electron donating group (para-hydroxyl benzaldehyde) will increase the anti-inflammatory activity of naproxen.

IONIZATION OF ORGANIC COMPOUNDS: III. BASICITIES OF PROPIONIC ACID AND PROPIONAMIDE

1962 ◽  
Vol 40 (5) ◽  
pp. 966-975 ◽  
Author(s):  
J. T. Edward ◽  
I. C. Wang
Keyword(s):  
Sulphuric Acid ◽  
Propionic Acid ◽  
Organic Compounds ◽  
Acid Concentration ◽  
Ultraviolet Absorption ◽  
Protonation Constants ◽  
Acidity Function ◽  
Hammett Acidity Function ◽  
Ionization Ratio

Protonation constants (pKBH+) of −6.8 and −0.9 have been determined for propionic acid and propionamide, respectively, from measurements of their ultraviolet absorption in various concentrations of sulphuric acid. The ionization ratio of propionamide and of other amides increases more slowly than the Hammett acidity function, h0, with increase in acid concentration. This may be explained by assuming that in a given concentration of sulphuric acid the protonated amide is more heavily hydrated than the protonated Hammett indicator used to establish the h0 scale for this region of acid concentrations.

Sign in / Sign up

Export Citation Format

Share Document