THE PREPARATION OF 9-HYDROXYPYRAZOLO[3,4-b]QUINOLINES

1966 ◽  
Vol 44 (17) ◽  
pp. 2009-2014 ◽  
Author(s):  
R. T. Coutts ◽  
J. B. Edwards
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Sodium Borohydride ◽  
Sodium Acetate ◽  
The Other ◽  
Reduction Product ◽  
Type I

4-(2-Nitrobenzylidene)-2-pyrazolin-5-ones (I) were best prepared by heating o-nitrobenzaldehyde and 2-pyrazolin-5-ones in acetic anhydride containing fused sodium acetate (cf. Erlenmeyer azlactone synthesis). Pyrazolones of type I were reductively cyclized with cyclohexene and palladium–charcoal, and gave 3a,4,9,9a-tetrahydro-9-hydroxy-1H-pyrazolo-[3,4-b]quinolines (II) which, as expected, were amphoteric compounds. Of the three other methods of reduction used in this study, two (zinc and acetic acid; sodium borohydride and palladium–charcoal) were capable of producing pyrazoloquinolines, but were less reliable. The other method employed (hydrazine hydrate and palladium–charcoal) caused degradation of the pyrazolone molecule in the two cases examined, and in both, bis(2-aminobenzylidene) hydrazine (V) was the reduction product isolated.

An efficient synthesis of pterosin C and other pterosins

1984 ◽  
Vol 62 (10) ◽  
pp. 1945-1953 ◽  
Author(s):  
Kam-Mui Eva Ng ◽  
Trevor C. McMorris
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Methyl Ether ◽  
Sodium Acetate ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Trans Isomers ◽  
Cis And Trans Isomers ◽  
Cis And Trans

A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

2010 ◽  
Vol 65 (12) ◽  
pp. 1509-1515 ◽  
Author(s):  
Manjunatha Kumsi ◽  
Boja Poojary ◽  
Prajwal Lourdes Lobo ◽  
Nalilu Suchetha Kumari ◽  
Anoop Chullikana
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Good Yield ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
One Pot ◽  
Biological Studies ◽  
Elemental Analyses

The key precursor rac-2-(4-isobutylphenyl)ethyl-1,2,4-triazole-5-thione (3) was synthesized in good yield from Ibuprofen (1). One-pot three-component reactions of 3 with 5-aryl-furan-2-carboxaldehydes/ substituted aromatic aldehydes and monochloroacetic acid in acetic acid in the presence of acetic anhydride and anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities.

scholarly journals Chlorocruoroporphyrin: a Simple Method of Preparation

1953 ◽  
Vol 32 (2) ◽  
pp. 365-366 ◽  
Author(s):  
Gilbert Y. Kennedy
Keyword(s):  
Acetic Acid ◽  
Hydrazine Hydrate ◽  
Potassium Permanganate ◽  
Sodium Acetate ◽  
Glacial Acetic Acid ◽  
Small Sample ◽  
Mixed Crystals ◽  
Distilled Water ◽  
Simple Method ◽  
Marine Polychaete

Munro Fox (1926, Addendum, p. 219) described a method of preparation of chlorocruoroporphyrin from the blood of the marine polychaete worm Spirographis. This was based upon the very troublesome method of Nencki & Zaleski (1900), which is time-consuming and wasteful. Furthermore, Spirographis is not easily obtainable in this country. Lemberg & Parker (1952) started with protoporphyrin, and by careful oxidation with potassium permanganate in acetone obtained a solution which gaVe mixed crystals of chlorocruoroporphyrin and diformyldeuteroporphyrin esters. Purification was by fractional chromatography. The procedure to be described here is simple and rapid, and could easily be carried out in one day by a biologist requiring a small sample of the porphyrin. The two methods mentioned above would not come into this category.This work was done at the Plymouth Laboratory, and I am very grateful to Mr T. R. Tozer of that laboratory for so kindly obtaining the animals for me and extracting the blood.The polychaete worms Myxicola infundibulum, Sabella pavonina and Branchiomma vesiculosum are all readily obtained from the muddy shores of the Salcombe estuary, especially on the Salstone. Blood was taken directly from the vessels of about 100 assorted worms by syringe, and squirted as it was removed from the worms into a mixture of peroxide-free ether (3 parts) and ‘Analar’ glacial acetic acid (1 part). After all the blood had been added, the mixture was well shaken and allowed to stand in the ice-chest for 30 min. The acetic acid was then washed out with distilled water, the first few washings containing a little sodium acetate to avoid washing out of the pigment, and the remaining solution of chlorocruorohaematin dried roughly by filtering through ether-soaked paper into a distilling flask and evaporated to dryness. 100 ml. of a 50% solution of hydrazine hydrate in glacial acetic acid were then added, and the mixture heated on a water-bath at 90° C. for 10 min.

Fluorine-Containing Heterocycles: Part I. Synthesis of New 7-(2-thienyl)-9-Trifluoromethylpyrido[3′,2′:4,5]Thieno[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems

2005 ◽  
Vol 2005 (3) ◽  
pp. 147-154 ◽  
Author(s):  
Etify A. Bakhite ◽  
Abdu E. Abdel-Rahman ◽  
Elham A. Al-Taifi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Methyl Iodide ◽  
Phosphorus Oxychloride ◽  
Diethyl Malonate ◽  
Triethyl Orthoformate ◽  
Dimroth Rearrangement ◽  
Ethyl Chloroacetate

3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxamide (3) and 2-carbonitrile analogue 5 were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with chloroacetamide or chloroacetonitrile respectively. Heating compound 3 with triethyl orthoformate led to the formation of pyridothienopyrimidinone derivative 6. Reaction of 6 with phosphorus oxychloride produced 4-chloropyrimidine derivative 7 which underwent some nucleophilic displacements upon treatment with thiourea, piperidine, morpholine or hydrazine hydrate to give the target 4-substituted pyridothienopyrimidines 8, 10a, 10b and 11 respectively. Reaction of compound 8 with methyl iodide or ethyl chloroacetate gave compounds 9a,b. The condensation of 3-amino-6-(2-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carbonitrile (5) with triethyl orthoformate led to the formation of methanimidate derivative 21 which upon treatment with hydrazine hydrate gave the target 3-amino-3,4-dihydro-4-imino-7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d]pyrimidine (22). The reactions of compounds 11 and 22 with some reagents namely; triethyl orthoformate, acetic anhydride, formic acid, acetic acid, acetylacetone benzaldehyde and/or diethyl malonate were carried out and their products were identified, in most cases as [1,2,4]triazolopyridothienopyrimidines via Dimroth rearrangement.

Cyclisation of 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoins

1981 ◽  
Vol 36 (4) ◽  
pp. 501-504 ◽  
Author(s):  
A. F. A. Shalaby ◽  
M. A. Abdel Aziz ◽  
S. S. M. Boghdadi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Mannich Bases ◽  
Anhydrous Sodium Acetate ◽  
Primary Aromatic Amines ◽  
Hydantoin Derivatives

Abstract 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoin derivatives (3a-f) were cyclised with acetic anhydride to give the bicyclic products (4a-f). Compounds 4 a, b condensed with aromatic aldehydes in acetic acid and in presence of anhydrous sodium acetate yielding the corresponding arylidene derivatives (5a-c). Compounds 4a, b also couple with aryldiazonium salts to give the expected coloured arylazo compounds (6a-j). 4 a, b reacted with formaldehyde and primary aromatic amines in ethanol to give the corresponding Mannich bases (7a-f).

The Nitration of α- and β-Acylnaphthalenes

1995 ◽  
Vol 48 (12) ◽  
pp. 1969 ◽  
Author(s):  
SD Barker ◽  
K Wilson ◽  
RK Norris
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Nitro Compound ◽  
Nitro Compounds ◽  
The Other ◽  
Coupling Constant ◽  
Significant Extent ◽  
Nitro Derivatives ◽  
High Yields

The nitration of α- and β- acylnaphthalenes with copper(II) nitrate in acetic anhydride or nitric acid/acetic acid mixtures gives high yields of the corresponding mononitro compounds. The assignment of constitution to these products is made on the basis of extensive 1H n.m.r. chemicl shift and coupling constant data. In the case of α- acylnaphthalenes, with the notable exception of α- pivalonaphthone, nitration occurs in the α-positions of the unsubstituted ring to give mixtures of 5- and 8-nitro compounds. α- Pivalonaphthone gives appreciable amounts of the 4-nitro compound and also of the 8-nitro compound. This result indicates that the pivaloyl group does not shield the 8-position sterically to any significant extent and is effectively electronically neutral, unlike the other acyl substituents , in allowing attack at the α-position (position 4) of the acylated ring. This result is ascribable to the lack of coplanarity of the pivaloyl group with the naphthalene system. All of the β- acylnaphthalenes gave mixtures of 4-, 5- and 8-nitro derivatives in proportions that did not vary significantly with the nature of the acyl group.

scholarly journals Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-Ones and 1,2,4-Triazin-6(5H)-Ones Classes

2019 ◽  
Vol 70 (11) ◽  
pp. 3769-3774
Author(s):  
Elena Valentina Rosca ◽  
Theodora Venera Apostol ◽  
Constantin Draghici ◽  
Octavian Tudorel Olaru ◽  
Laura Ileana Socea ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Sodium Acetate ◽  
Artemia Salina ◽  
Ft Ir ◽  
New Compounds ◽  
Acetic Acids

This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays.

scholarly journals Synthesis of New Pyrazoline - Phenoxathiin Derivatives

2013 ◽  
Vol 10 (2) ◽  
pp. 405-419
Author(s):  
Baghdad Science Journal
Keyword(s):  
Acetic Acid ◽  
Hydrazine Hydrate ◽  
Aromatic Aldehyde ◽  
Aluminum Chloride ◽  
Heterocyclic Compounds ◽  
Diphenyl Ether ◽  
The Other ◽  
Anhydrous Aluminum Chloride ◽  
Phenyl Hydrazine ◽  
Pyrazoline Ring

Phenoxathiin was prepared by the reaction of diphenyl ether with sulfur in the presence of anhydrous aluminum chloride. This work comprised the synthesis of new phenoxathiin derivatives containing heterocyclic moieties. These heterocyclic compounds were synthesized in three groups. The first group was made up of 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) obtained from the reaction of 2-acetylphenoxathiin with different aromatic aldehyde in the presence of sodium hydroxide. The other two groups involved compounds produced from the reaction of (3a-3j) with hydrazine hydrate in acetic acid to get 2-(1-acetyl pyrazolin-3-yl) phenoxathiin derivatives (4a-4j), and phenyl hydrazine in the presence of piperidine to afford 2-(1-phenyl pyrazolin-3-yl) phenoxathiin derivatives (5a-5j). All these compounds of two groups above were substituted in position (5) in pyrazoline ring with different aryl groups according to aromatic aldehyde used in the preparation of the first group series compounds.

scholarly journals Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-Ones and 1,2,4-Triazin-6(5H)-Ones Classes

2019 ◽  
Vol 70 (11) ◽  
pp. 3769-3774
Author(s):  
Elena Valentina Rosca ◽  
Theodora Venera Apostol ◽  
Constantin Draghici ◽  
Octavian Tudorel Olaru ◽  
Laura Ileana Socea ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Sodium Acetate ◽  
Artemia Salina ◽  
Ft Ir ◽  
New Compounds ◽  
Acetic Acids

This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays.

scholarly journals Regioselective convergent synthesis of 2-arylidene thiazolo[3,2-a]pyrimidines as potential anti-chikungunya agents

RSC Advances ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 5191-5195 ◽  
Author(s):  
Mohamed Fares ◽  
Patrick M. McCosker ◽  
Muhammad A. Alsherbiny ◽  
Anthony C. Willis ◽  
Timothy Clark ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Sodium Acetate ◽  
Anhydrous Sodium Acetate ◽  
Regioselective Synthesis ◽  
One Pot ◽  
Bromoacetic Acid ◽  
Convergent Synthesis ◽  
The One

Convergent and convenient regioselective synthesis of novel thiazolo[2,3-a]pyrimidines was accomplished using the one-pot reaction of 6-ethylthiouracil, bromoacetic acid, anhydrous sodium acetate, acetic anhydride, acetic acid and suitable aldehyde.

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