Showing papers on "Pyrazole published in 1977"
TL;DR: A number of metal salts of pyrazole are reported in this article, where the pyrazolato ion acts as a bidentate, and tetrahedral or square planar surrounded metal ions are found.
34 citations
TL;DR: In this paper, the mixed bis(arylhydrazones) of l - threo -2,3-hexodiulosono-1,4-lactone rearrange into pyrazolediones.
32 citations
TL;DR: The structure of azole organotin compounds depends on the position of the nitrogen atoms in the aromatic ring as mentioned in this paper, with at least two nitrogens in the 1-3 position in the ring giving the corresponding organotin derivatives which have a polymeric structure.
27 citations
TL;DR: The reactivity of organosilylamines of imidazole, pyrazole, 1,2,4-triazole and benzotriazole towards alkyl halides, acidic chlorides and halogenated ketones has been studied as discussed by the authors.
27 citations
26 citations
Journal Article•
TL;DR: Several isotopic variants of pyrazole, both stable and radioactive, were used in a study of its metabolic fate by gas chromatography-mass spectrometry, and the use of d3-pyrazole greatly enhanced structural assignment of the metabolites by revealing the metabolism at or next to a labeled carbon atom.
Abstract: Pyrazole has been widely used as an inhibitor of alcohol dehydrogenase both in vivo and in vitro. Very little attention has been paid to the metabolism of this agent and possible biological activity of any metabolites. Several isotopic variants of pyrazole, both stable and radioactive, were used in a study of its metabolic fate by gas chromatography-mass spectrometry. Seven metabolites were structurally identified and included hydroxylated and conjugated derivatives of pyrazole. Two metabolites were conjugated with a pentose, perhaps indicating that pyrazole serves as a substrate in the salvage pathway of purines and pyrimidines forming pyrazole ribosides. The use of d3-pyrazole greatly enhanced structural assignment of the metabolites by revealing the metabolism at or next to a labeled carbon atom.
23 citations
TL;DR: A number of compounds derived from 7, 8-dihydro-5(6H)-quinolinone were synthesized and characterized and screened for their in vitro inhibitory activity against Bacillus subtilis and Pseudomonas fluorescens.
Abstract: Pyrazole-, pyrazolone- and isoxazole-containing systems were prepared from 3,4-dihydro-6-(hexyloxy)-1(2H)-naphthalenone, 3,4-dihydro-6-(hexadecyloxy)-1(2H)-naphthalenone,3,4-dihydro-6(2-dimethylaminoethyloxy)-1-(2H)-naphthalenone, 3,4-dihydro-7-hexyloxy-1(2H)-phenanthrone, and 3,4-dihydro-7-(2-dimethylaminoethyloxy)-1(2H)-phenanthrone. A number of compounds derived from 7, 8-dihydro-5(6H)-quinolinone were also synthesized and characterized. Both hydrophilic and lipophilic groups were incorporated into certain systems as well as cidal groups. The compounds were screened for their in vitro inhibitory activity against Bacillus subtilis and Pseudomonas fluorescens. Structure-acitivity relationships among the molecular systems are discussed.
22 citations
TL;DR: The tetrazole 5 reacts at 165-170° or on irradiation at room temperature to yield 2-phenyl-3,3a-dihydrochromano[4,3-c]pyrazole as mentioned in this paper, which probably arises by intramolecular [3+2]-cycloaddition of the intermediate nitrilimine.
Abstract: Thermal and Photochemically Induced Interamolecular 1,3-Dipolar Cycloaddition Reactions of 5-(2-Allyloxyphenyl)-2-phenyltetrazole
The title compound 5 is easily obtained by a recently described procedure (Scheme 2). The tetrazole 5 reacts at 165–170° or on irradiation at room temperature to yield 2-phenyl-3,3a-dihydrochromano[4,3-c]pyrazole (7, Scheme 3), which probably arises by intramolecular [3+2]-cycloaddition of the intermediate nitrilimine. Dehydrogenation of 7 with chloranil leads to 2-phenylchromano[4,3-c]pyrazole (8, Scheme 3).
21 citations
Patent•
12 Aug 1977
TL;DR: A pyrazole derivative of formula I (X and Y are H, halogen, or methylsulfonyl, provided that at least one of X and Y is methyl sulfonyl; Z is lower alkyl; R is 2,4-dinitrophenyl, benzyl, phenacyl, or pivaloylmethyl).
Abstract: NEW MATERIAL:A pyrazole derivative of formula I (X and Y are H, halogen, or methylsulfonyl, provided that at least one of X and Y is methylsulfonyl; Z is lower alkyl; R is 2,4-dinitrophenyl, benzyl, phenacyl, or pivaloylmethyl). EXAMPLE: 1,3-Dimethyl-4-( 2-chloro-4-methylsulfonylbenzoyl )-5-(pivaloylmethoxy) pyrazole. USE: Herbicide effective to harmful weeds such as barnyard grass and umbrella sedge, and essentially harmless to the crop such as rice plant. PROCESS: The rearrangement reaction of a compound of formula II affords a compound of formula III, which is reacted with a compound of formula Hal-R in a solvent such as methyl ethyl ketone in the presence of an alkaline substance such as potassium carbonate to obtain the objective compound of formula I. COPYRIGHT: (C)1981,JPO&Japio
16 citations
15 citations
TL;DR: In sulphuric acid, 1,4,5-trimethylimidazole 3-oxide and 1-methylpyrazole 2-oxide are nitrated as the free bases at C-2 and C-5, respectively as mentioned in this paper.
Abstract: In sulphuric acid, 1,4,5-trimethylimidazole 3-oxide and 1-methylpyrazole 2-oxide are nitrated as the free bases at C-2 and C-5, respectively. At high acidities the pyrazole gives 1-methyl-3,5-dinitropyrazole 1-oxide. With phosphorus trichloride the pyrazole oxides were deoxygenated, and with phosphoryl chloride, 1-methylpyrazole 2-oxide gave 5-chloro-1-methylpyrazole. 1-Methyl-5-nitropyrazole 2-oxide with acetyl chloride gave 5-chloro-1-methyl-4-nitropyrazole.
TL;DR: A number of the products of dipolar addition have been converted into new D-ribofuranosyl-pyrazoles and -triazoles by hydrogenolysis.
TL;DR: In this article, the ESR spectra at X and Q-band frequencies of Cu(II) doped Cd(pyrazole)2Cl2 are discussed in terms of a compressed tetragonal symmetry built up by a chromophore CuCl4N2.
TL;DR: The reaction of α-diazoacetophenone (1) with methanolic sodium methoxide in dilute solution gives 3-benzoyl-5-hydroxy-4-phenylpyrazole (4), 3-bensoyl, 4-hydroxal 2-monohydrazone (37), and tetrazole as mentioned in this paper.
Abstract: The reaction of α-diazoacetophenone (1) with methanolic sodium methoxide in dilute solution gives 3-benzoyl-5-hydroxy-4-phenylpyrazole (4), 3-benzoyl-4-hydroxy-5-phenyl-pyrazole (5), 3-benzoyl-5-methoxy-4-phenylpyrazole (9), 3-benzoyl-4-phenylpyrazole (6), 5-benzoyltetrazole (7), 3,6-dibenzoyldihydro-s-tetrazine (10), cis- and trans- β-benzoyl- α-phenyl-acrylic acid, acetophenone, methyl benzoate, and benzoic acid. The pyrazoles 4, 5, and 9 are considered to arise via reaction of 1 to give α-methoxyacetophenone followed by further reaction of the anion of the latter with 1. Evidence in accord with this view was obtained by a study of the products formed when 1 was treated with methanolic sodium methoxide in the presence of 2-methoxy-4′-methylacetophenone. Acetophenone is considered to arise by reduction of 1 via phenylglyoxal 2-monohydrazone (37); condensation of 1 with the enolate ion derived from acetophenone then can give the pyrazole 6, while condensation of 1 with 37 could give the tetrazole 7.
Patent•
18 Feb 1977
TL;DR: In this article, the authors describe a dye of the formula where X is hydrogen, chlorine, bromine, cyano, nitro, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyls, methoxy or ethoxy.
Abstract: Uniformly dyed water-swellable cellulosic fibers obtained by dyeing cellulosic fibers, in the swollen state, with a dye of the formula ##STR1## where X is hydrogen, chlorine, bromine, cyano, nitro, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, methoxy or ethoxy, Y is hydrogen, chlorine, bromine, cyano or nitro, Z is a radical of the formula ##STR2## Q is oxygen or sulfur, R 1 is alkyl of 1 to 4 carbon atoms, methoxymethyl, phenoxymethyl or phenyl which is unsubstituted or substituted by chlorine, bromine, nitro, methyl, methoxy or ethoxy, R 2 is hydrogen, methyl, ethyl, phenyl or phenyl substituted by chlorine, bromine or methyl, R 3 is hydrogen, methyl or, if R 2 is methyl, is C 1 to C 4 alkoxycarbonyl, R 2 and R 3 together with the linking carbon atoms are phenylene or phenylene substituted by chlorine, methyl, methoxy or ethoxy and K is a radical of a coupling component selected from the pyrazolone, pyrazole, indole, quinolone or homophthalimide series
TL;DR: The reactivities of organotin derivatives of pyrazole, imidazole, 1,2,4-triazole and benzotriazole with acetyl or benzoyl chloride and α- or β-halogenated ketones have been studied.
TL;DR: In this paper, 2-thiocyanatomethylen-cycloalkanone (2-THIOCYCLO) was derived from the corresponding 2-chlormethylene-cycloen-cycloealkanones.
Abstract: 2-Thiocyanatomethylen-cycloalkanone-(1) 2 wurden aus den entsprechenden 2-Chlormethylen-cycloalkanonen-(1) 1 dargestellt. Bei der Umsetzung mit substituierten Phenylhydrazonen isolierten wir 2,4-Dinitrophenylhydrazone (4b, 4c und 4e) bzw. 1,2,3-Thiadiaziniumperchlorate (5a, 5a′) sowie substituierte Pyrazole (7e, 7f). Die Reaktion von 2 mit flussigem Ammoniak fuhrte sowohl zu Isothiazolen (8a, 8b) als auch Bis-(2-acyl-vinyl)-sulfiden (9c, 9f).
β-Thiocyanato-Vinylcarbonyl Compounds. IV. Preparation and Reactions of 2-Thiocyanatomethylene-cycloalkanones-(1)
2-Thiocyanatomethylene-cycloalkanones-(1) 2 were obtained from the corresponding 2-chlormethylene-cycloalkanones-(1) 1. On reaction with substituted phenylhydrazines, the 2,4-dinitrophenylhydrazones 4b, 4c and 4e, 1,2,3-thiadiaziniumperchlorates 5a and 5a′, and the substituted pyrazoles 7e and 7f, were isolated, respectively. From reaction of 2 with liquid ammonia, the isothiazoles 8a and 8b as well as the bis-(2-acyl-vinyl)-sulfides 9c and 9f were obtained.
TL;DR: The reaction of I with ethyl and phenyl hydrazinecarboxylates (IIe,f) led to the formation of the hydrazones (VIe) and (VIf), respectively, with methyl-and phenylhydrazines it produced the pyrazoles (X) and XI, respectively.
Patent•
21 Oct 1977
TL;DR: In this article, the authors proposed a set of novel compounds falling under the general formula: where R 1, R 2 and R 3 are substituents, e.g. alkyl and Me is hydrogen or a metal cation.
Abstract: The present invention concerns certain novel compounds falling under the general formula: ##STR1## WHEREIN R 1 , R 2 and R 3 are substituents, e.g. alkyl and Me is hydrogen or a metal cation. The compounds are useful stabilizers of organic material against the degradative effect of heat, oxidation and U.V. light.
TL;DR: In this article, the reaction of 3c (R=2-pyridyl, R1=CN, R2=CO2C2H5) gave a dimer, the 2,3,7,9,10-pentaazadodeca-1,4,8,11-tetraene derivative (9), instead of 4.
Abstract: Amidrazones RC(NH2)=NNH2 (1a, b) (R=2-pyridyl, phenyl) reacted with EtOCH=CR1R2 (2a–d) (R1R2=CN, CO2C2H5, COCO2C2H5) to give RC(NH2)=NNHCH=CR1R2 (3a–g). 3,4-Disubstituted pyrazoles (4a, b) were obtained on the heating of 3a, b, e, and f (R=2-pyridyl, phenyl, R1=CN, R2=CN, CO2C2H5) in toluene. However, the heating of 3c (R=2-pyridyl, R1=R2=CO2C2H5) gave a dimer, the 2,3,7,9,10-pentaazadodeca-1,4,8,11-tetraene derivative (9), instead of 4. 5-Amino-6-ethoxycarbonyl-3-(2-pyridyl)-1H-1,2,4-triazepine (10) was obtained by the reaction of 3a (R=2-pyridyl, R1=CN, R2=CO2C2H5) with ethanolic hydrogen chloride. The treatment of 10 with alkaline gave 2,9-di-2-pyridyl-6,7,13,14-tetrahydro-4H,11H-[1,5]diazocino-[2,3-e:6,7-e′]di[1H-1,2,4]triazepine-6,13-dione (11). Triazepine (10) reacted with hydrazines to give 5-hydrazino-1H-1,2,4-triazepine derivatives (13a, b).
Patent•
26 Jan 1977TL;DR: Unsymmetrical chromium mixed complex dyestuffs of the formula ##STR1## are suitable for the dyeing and printing of nitrogen-containing fibrous materials in yellow shades as mentioned in this paper.
Abstract: Unsymmetrical chromium mixed complex dyestuffs of the formula ##STR1## wherein R1 and R2 denote C1 -C4 -alkyl, nitrile, carbonamide or X-Z, X denotes a direct bond or a bridge member to a C atom of the rings A, B, C or D or to a 3-C atom of the pyrazoles and Z denotes SO3 H, COOH or OSO3 H and A, B, C and D can possess further substituents, are suitable for the dyeing and printing of nitrogen-containing fibrous materials in yellow shades.
Patent•
20 Dec 1977
TL;DR: In this paper, a method of preparation of biological compounds possessing biological properties, capable of decreasing the sugar level in blood, was described, and the method of their preparation was described.
Abstract: N-{4-[2-(Pyrazole-1-carbonamide)-ethyl]-benzenesulphonyl}-ureas of the formula 1 ##STR1## wherein R, R2 are a hydrogen atom or lower alkyl of up to 4 carbon atoms, R1 is a hydrogen, chlorine or lower alkyl atom containing up to 4 carbon atoms and R3 is an alkyl of 2 to 5 carbon atoms or cycloalkyl of 5 to 6 carbon atoms, and their method of preparation is described, said compounds possessing biological properties, capable of decreasing the sugar level in blood.
TL;DR: In this article, a large excess of paraformaldehyde and potassium hydroxide in ethanol gave 3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-2-yn-1-ol (5) in 70% yield.
Abstract: Treatment of 2,3,5-ri-O-benzyl-β-D-ribofuranosylethyne (2) with a large excess of paraformaldehyde and potassium hydroxide in ethanol gave 3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-2-yn-1-ol (5) in 70% yield. Oxidation of (5) with chromic oxide (Jones reagent) afforded the carboxylic acid (4)(75%), esterification of which with diazomethane gave the known ester (7). Similar reactions and correlations have been carried out in the α-series.Reaction of the Grignard reagent (14) of 3-(tetrahydropyran-2-yloxy)propyne with 2,3,5-tri-O-benzyl-D-ribofuranose (19) followed by ring closure and removal of the tetrahydropyranyl ether group gave the alcohol (5) in 52% overall yield.Careful oxidation of (5) gave the corresponding aldehyde (3) which yielded the known pyrazole (1)(72%) on treatment with hydrazine. When 1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-yn-3-ulofuranose (22) was treated with hydrazine, 3(5)-(1,2:4,5-di-O-isopropylidene-D-manno-pentahydroxypentyl)pyrazole (23) was isolated in 93% yield.
TL;DR: In this paper, it was shown that pyrazolines photosensitize the degradation of lysozyme, the tryptophan, histidine and methionine residues being the main sites of attack.
Abstract: Ultraviolet irradiation of the diaryl-2-pyrazoline (1) in water gives the corresponding pyrazole (3), the 4-hydroxypyrazole (4) and several unidentified products. Irradiation of the tetraaryl-2-pyrazoline (2) gives the pyrazole (6) as the major product. The rates of photodegradation are increased if lysozyme is present and the corresponding pyrazoles are formed preferentially. Pyrazoles are also the major products when wool containing (1) or (2) is irradiated. Both pyrazolines photosensitize the degradation of lysozyme, the tryptophan, histidine and methionine residues being the main sites of attack.
TL;DR: In this paper, the IR spectra of tin(IV) halides with pyrazole, 3(5)methyl pyrazoles and 3,5-dimethyl pyrazolines of the type SnX4·L2 were obtained.
TL;DR: In this paper, 3-Aminoacrylonitriles are postulated as intermediates in some rearrangements of pyrazoles to imidazoles.
Abstract: Irradiation of 1,4,5-triphenylpyrazole in the presence of iodine gives 1-phenyl-1H-phenanthro[9,10-c]pyrazole, identical with a specimen prepared by an independent route. 1,3,4-Triphenylpyrazole does not react under these conditions; this is thought to be because the intermediate non-aromatic polyene would be dipolar. Irradiation of 1,4,5-triphenylpyrazole in the presence of benzophenone gives 3-anilino-2,3-diphenylacrylonitrile, which is itself inert towards irradiation. 3-Aminoacrylonitriles are postulated as intermediates in some rearrangements of pyrazoles to imidazoles.
TL;DR: Binding experiments performed on partially alkylated liver alcohol dehydrogenase indicate that coenzyme binding is normal at a subunit adjacent to an alkylation protomer even though active ternary complexes cannot be formed.