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1.
Benzothiazol-2-yl glyoxylic acid and α-amino-benzothiazol-2-yl acetic acid hydrochloride undergo decarboxylation at room temperature. This facile decarboxylation seems to depend on the following requirements: (a) the formation of a planar zwitterion; (b) a distance of about 2.2 Å between the charges of the zwitterion; (c) the stabilisation of the intermediate carbanion. In fact the following compounds which do not fulfil these three conditions do not decarboxylate at room temperature: α-hydroximino benzothiazol-2-yl acetic acid, α-amino benzothiazol-2-yl acetic acid as internal salt, benzothiazol-2-yl acetic acid, 3-(benzothiazol-2-yl)-propionic acid and benzothiazol-2-yl pyruvic acid. 相似文献
2.
2-(p-Acetylaminobenzenesulfonylamido)-substituted benzothiazoles were prepared from 2-amino-substituted benzothiazoles and
p-acetamidobenzenesulfonyl chloride using a mixture of pyridine and Ac2O, which formed an electrophilic N-acetyl- pyridinium complex facilitating condensation to give the desired products by removal
of HCl. 2-[4-(Substituted benzothiazol-2-yl)aminosulfonylanilino]pyridine-3-carboxylic acids (synthesized from 2-chloropyridine-3-carboxylic
acid and the corresponding substituted 2-(p-aminobenzenesulfonylamido)benzothiazole in 2-ethoxyethanol using Cu-powder and
K2CO3) were then converted to acid chlorides, which on further reaction with piperazine and 4-methoxyphenylpiperazine yielded the
corresponding 2-[4-(substituted benzothiazol-2-yl)amino-sulfonyl]anilino-3-(piperazinocarbonyl) pyridine and 2-[4-(substituted
benzothiazol-2-yl)amino-sulfonyl]anilino-3-[(4-methoxyphenyl)piperazin-1-yl-carbonyl]pyridine. The structures of the new compounds
have been established on the basis of their elemental analyses as well as IR, 1H NMR, and mass-spectral data. All the compounds have been screened for antimicrobial activity and found to possess considerable
antibacterial activity. 相似文献
3.
P. V. Savitskii R. I. Vas’kevich Yu. L. Zborovskii V. I. Staninets S. A. But A. N. Chernega 《Russian Journal of Organic Chemistry》2008,44(3):402-406
1-(Benzothiazol-2-yl)-4-phenylthiosemicarbazide reacted with methyl iodide in the presence of sodium acetate in boiling ethanol to give 2,2′-dithiobis[N-(5-methylsulfanyl-4-phenyl-4H-1,2,4-triazol-3-yl)-benzenamine]. The reaction of the title compound with dimethyl acetylenedicarboxylate in dioxane led to the formation of methyl 3-(benzothiazol-2-yl)-2-(2-methoxy-2-oxoethyl)-2,3-dihydro-1,3,4-thiadiazole-2-carboxylate. 相似文献
4.
N. S. Boltacheva L. N. Dianova P. A. Slepukhin V. I. Filyakova V. A. Bakulev V. N. Charushin 《Russian Journal of Organic Chemistry》2014,50(6):767-777
Fluoroalkyl-substituted lithium 1,3-diketonates reacted with 4-hydrazinyl-6-methylpyrimidin-2-amine, 2,6-dimethylpyrimidin-4-ylhydrazine, 7-fluoroquinoxalin-6-ylhydrazine, and benzothiazol-2-ylhydrazine to give the corresponding hetaryl-substituted pyrazoles. The molecular and crystal structures of 4-methyl-6-(3-methyl-5-trifluoromethyl-1H-pyrazol-1-yl)pyrimidin-2-amine and 4-(5-difluoromethyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)-6-methylpyrimidin-2-amine were determined by X-ray analysis. 相似文献
5.
Vyacheslav Ya. Sosnovskikh Dmitri V. Sevenard Viktor O. Iaroshenko 《Tetrahedron》2010,66(36):7322-7328
The reactions of 3-formylthiochromone with o-phenylenediamines, o-aminobenzenethiol, and indoles proceeded at the aldehyde group to give 3-(benzimidazol-2-yl)thiochromone, 3-(benzothiazol-2-yl)thiochromone, and 3-di(indol-3-yl)methylthiochromones, respectively. 3-Formyl- and 3-cyanothiochromones react with primary aromatic amines and phenylhydrazine to give the corresponding anils and phenylhydrazones of 3-formyl- and 2-amino-3-formylthiochromones. The reaction of 3-cyanochromones with o-phenylenediamines gave 2-amino-3-[(2-aminophenyl)iminomethyl]-4H-chromen-4-ones. 相似文献
6.
Two new iridium(III) complexes containing benzothiazol-2-yl carbazole derivative as a cyclometalated ligand (L) and picolinate (pic) or acetylacetonate (acac) as the ancillary ligand, Ir(III) bis(3-(benzothiazol-2-yl)-9-butyl-carbazole)(picolinate) [Ir(L)2(pic)] and Ir(III) bis(3-(benzothiazol-2-yl)-9-butyl-carbazole)(acetylacetonate) [Ir(L)2(acac)], were synthesized and characterized by elemental analysis, 1H NMR, FT-IR, and UV–Vis absorption spectra. Both the iridium(III) complexes emit intense green–yellow emissions, indicating that they are useful for the fabrication of organic light-emitting diodes. 相似文献
7.
G. N. Dorofeenko A. V. Koblik T. I. Polyakova 《Chemistry of Heterocyclic Compounds》1973,9(7):809-811
The synthesis of dimethyl benzothiazol-2-yl, 2-thienyl, and 1-methylbenzimidazol-2-yl carbinols and their acylation with acetic anhydride in the presence of perchloric acid have been performed. A method for the synthesis of 4-(benzothiazoI-2-yl)-2,6-dimethylpyrylium and 4-(2-thienyl)-2,6-dimethylpyrylium perchlorates has been developed; these substances are converted by treatment with aqueous ammonia, into the corresponding 4-(2-hetaryl)-2,6-di-methylpyridines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 878–880, July, 1973. 相似文献
8.
Krayushkin M. M. Stoyanovich F. M. Zolotarskaya O. Yu. Murav"ev I. V. Martynkin A. Yu. Uzhinov B. M. 《Russian Chemical Bulletin》2001,50(12):2420-2423
Dithienylethenes containing the thiophene rings with benzothiazolyl substituents in position 2 were synthesized. 1,2-Bis[2-(benzothiazol-2-yl)benzothiophen-3-yl]hexafluorocyclopentene and 1,2-bis[2,5-di(benzothiazol-2-yl)-3-thienyl]hexafluorocyclopentene possess photochromic properties. The open forms of 1,2-bis(2-benzothiazolylhetaryl)ethenes fluoresce, but introduction of the benzothiazole rings into dihetarylethenes significantly lowers the fatigue resistance of photochromes and favors thermal reversibility. 相似文献
9.
S. L. Nikitenko M. G. Kaplunov I. K. Yakushchenko S. B. Echmaev 《Russian Chemical Bulletin》2017,66(6):980-985
A dual function (electroluminescence and photosensitivity) of devices based on bis{N-[2-(benzothiazol-2-yl)phenyl]-N-(4-methylphenylsulfonyl)amido}zinc was studied. It was shown that both luminescent and photovoltaic properties are strongly dependent on exсiplex formation. 相似文献
10.
A series of gem-difluoroolefin derivatives were synthesized in moderate to good yields by the reaction of α,α-difluoro-β-carbonyl benzothiazol-2-yl sulfones (DFBTs) with various carbon nucleophiles. Using dl-proline as organocatalyst, the reaction of DFBT with acetone gave a tertiary alcohol, which could be further converted to the corresponding difluoroolefin by LDA. 相似文献
11.
V. M. Zubarovskii 《Chemistry of Heterocyclic Compounds》1973,9(11):1397-1399
In an aqueous medium, the reaction of N-sodio-2-methylbenzimidazole with monohalogen-substituted nitrogenous aromatic heterocycles containing the halogen in the position to the nitrogen atom may be considered as amethod for obtaining N-betaryl-2-methylbenzimidazoles. 1-(Benzoxazol-2-yl)- and 1-(benzothiazol-2-yl)-2-methylbenzimidazoles have been synthesized; imidacyanine dyes have been obtained with benzothiazol-2-yl groups on the nitrogen atoms of the benzimidazole nuclei from the methiodide of the latter.For Communication V, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1542–1544, November, 1973. 相似文献
12.
A N el-Shorbagi S Sakai M A el-Gendy N Omar H H Farag 《Chemical & pharmaceutical bulletin》1989,37(11):2971-2975
3-[2-[p-(Un)substituted phenyl]imidazo [2,1-b]benzothiazol-3- yl]propionic acid derivatives (2a--e) were prepared via the interaction of the corresponding 2-[p-(un)substituted phenyl]imidazo[2,1-b]benzothiazoles (1a--e) with acrylic acid in the presence of acetic anhydride and acetic acid. Esterification of 2a--e produced methyl esters (3a--e). Upon the interaction of 3a with m-chloroperbenzoic acid, the S-dioxide (4a) was obtained. Compound 5a was prepared from 4a by alkaline hydrolysis. Vilsmeier formylation for 1a--e produced novel [2-[p-(un)substituted phenyl]imidazo[2,1-b]benzothiazol-3- yl]formaldehyde derivatives (6a--e). Derivatives 6a--e reacted with ethyl bromoacetate to give ethyl 3-hydroxy-3-[2-[p-(un)substituted phenyl]imidazo[2,1-b]benzothiazol- 3-yl]propionate esters (7a--e). Compound dl-7a was resolved with l-(+)-tartaric acid. Compounds 2a--e showed weak or no activity in the carrageein-induced paw edema assay. Compound 4a significantly inhibited the leakage of pontamine-sky blue dye into the peritoneal cavity of mice, in the capillary permeability inhibition assay. Compound 5a inhibited the writhing by 62% in the acetic acid-induced writhing assay. 相似文献
13.
A series of benzothiazol-2-yl-dithiocarbamates 3a-d along with their copper complexes 4a-c were synthesized via the reaction of suitable alkyl, aralkyl or heteroaryl halides with the sodium salt of benzothiazol-2-yl-dithiocarbamic acid, followed by complexation with copper sulphate. N-(4-Acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl)-N-benzothiazol-2-yl-acetamides 7a-c were synthesized by cyclization of the appropriate thiosemicarbazones 6a-c in acetic anhydride. Selected compounds were screened for in vitro schistosomicidal activity against Schistosoma mansoni at three different dosage levels (10, 50 and 100 microg/mL). Three of these products, 4a-c, showed schistosomicidal activity similar to praziquantel, with 100% worm mortality at 10 microg/mL. These compounds would constitute a new class of potent schistosomicidal agents. 相似文献
14.
V. V. Nosyreva L. V. Andriyankova A. G. Mal''kina A. V. Afonin B. A. Trofimov 《Russian Journal of Organic Chemistry》2001,37(6):859-865
Nucleophilic addition of 2-mercaptobenzothiazole to 4-alkyl-4-hydroxy-2-alkynonitriles at 1:1 ratio in the presence of 4-6 wt% of Et3N occurs regio- and stereospecifically to afford (Z)-4-alkyl-3-(benzothiazolyl-2-thio)-4-hydroxy-2-alkenonitriles (yield 40-51%). In the presence of 1.3 wt% of Dabco the thiazole and 4-hydroxy-4-methyl-2-pentynonitrile (1:1) give rise to a mixture of 2-alkenonitrile and 2-(3,3,6,6-tetramethyl-2-cyanomethyl-5-cyanomethylene-1,4-oxathian-2-yl)thiobenzothiazole. At the use of 4-6 wt% of LiOH arises an intractable mixture containing 1,4-oxathiane, benzothiazol-2-one, 2-[1-(5,5-dimethyl-2-cyanomethyl)-4-cyanomethylene-1,3-oxathiolan-2-yl)-1-methylethyl]thiobenzothiazole, bis(2,2,5,5-tetramethyl-6-cyanomethyl-3-cyanomethylene-1,4-oxathian-6-yl) disulfide, bis[1-(5,5-dimethyl-2-cyanomethyl-4-cyanomethylene-1,3-oxathiolan-2-yl)-1-methylethyl] disulfide, and 3-[1-(5,5-dimethyl-2-cyanomethyl-4-cyanomethylene-1,3-oxathiolan-2-yl)-1-methylethyl]benzothiazol-2-one (according to 1H and 13C NMR data). 2-mercaptobenzothiazole adds to 3-phenyl-2-propynonitrile in the presence of 7 wt% of KOH with regio- and stereospecific formation of (Z)-3-(benzothiazolyl-2-thio)-3-phenyl-2-propenonitrile (88%). 相似文献
15.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2008,44(7):876-881
The reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyridin-2-ones with the nitrogen-containing 1,4-dinucleophiles
o-phenylenediamine, o-aminothiophenol, and ethylenediamine, proceeds as a recyclization, the products of which are derivatives
of 5-(1H-benzimidazol-2-yl)-2H-2-pyranone, 5-(benzothiazol-2-yl)-2H-2-pyranone, and 5-(4,5-dihydro-1H-imidazol-2-yl)-2H-2-pyra-none
respectively.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1089–1095, July, 2008. 相似文献
16.
Kenney BD Breslav M Chang R Glaser R Harris BD Maryanoff CA Mills J Roessler A Segmuller B Villani FJ 《The Journal of organic chemistry》2007,72(25):9798-9801
An efficient process to produce kilogram quantities of a key argininylbenzo[d]thiazole intermediate was developed for the preparation of the tryptase inhibitor RWJ-56423. A variety of activated arginine esters and benzo[d]thiazole nucleophiles were evaluated as coupling partners. Our work led to the selection and optimization of an argininyl imidazolide ester and benzothiazol-2-yl MgCl nucleophile. This paper focuses on the preparation, use, and stability of the benzothiazol-2-yl Grignard reagents. 相似文献
17.
Masakatsu Matsumoto Taichi Akimoto Yuki Matsumoto Nobuko Watanabe 《Tetrahedron letters》2005,46(36):6075-6078
Four bicyclic dioxetanes bearing a 4-(benzothiazol-2-yl)-3-hydroxyphenyl or 4-(benzoxazol-2-yl)-3-hydroxyphenyl group were synthesized. These dioxetanes underwent base-induced decomposition with accompanying emission of light with high efficiency in NaOH/H2O as well as in tetrabutyl ammonium fluoride (TBAF)/acetonitrile. Among them, benzothiazol-analogs decomposed faster in the aqueous solution than in acetonitrile. 相似文献
18.
Stey T Pfeiffer M Henn J Pandey SK Stalke D 《Chemistry (Weinheim an der Bergstrasse, Germany)》2007,13(13):3636-3642
Starting from tris(benzothiazol-2-yl)phosphane (1) an advanced Janus-head ligand, di(benzothiazol-2-yl)phosphane (2), was synthesised and structurally characterised. The heteroaryl substituents of this ligand provide both hard and soft donor sites. Surprisingly, the phosphorus atom in 2 is divalent and the hydrogen atom is directly bonded to one ring nitrogen atom and hydrogen bonded to the second. Compound 2 decomposes in any common solvent other than diethyl ether and a new preparation to improve the yields of 2 is presented. A coordination polymer, [{Cs(bth)(2)P}8] (3) (bth=benzothiazol-2-yl), was obtained when the sec-phosphane 2 was allowed to react with elemental caesium in a 1:1 ratio in diethyl ether at -78 degrees C. In 3 each anion is coordinated to four caesium cations and vice versa. The central phosphorus atom is coordinated to two metal atoms above and below the mean plane of the anion in positions in which the two lone pairs of a four-electron donor are anticipated. Two additional cations micro-bridge both ring nitrogen atoms. Hence both faces of the Janus-head ligand are coordinated to the same number of metal cations but in a different way. 相似文献
19.
S. N. Kovalenko M. V. Vasil'ev I. V. Sorokina V. P. Chernykh A. V. Turov S. A. Rudnev 《Chemistry of Heterocyclic Compounds》1998,34(12):1412-1415
Using o-phenylenediamines, o-aminophenol or o-aminothiophenol, 2-iminocoumarin-3-carboxamide can be recyclized to the corresponding
3-(1H-benzimidazol-2-yl), 3-(benzoxazol-2-yl), or 3-(benzothiazol-2-yl) coumarins. An alternative synthesis has been carried
out and an analytical comparison of the synthetic routes made.
For Communication 2 see [2].
Ukraine Pharmaceutical Academy, Khar'kov 310002. E-mail: kosn@ukrfa.kharkov.ua. Translated from Khimiya Geterotsiklicheskikh
Soedinenii, No. 12, pp. 1664–1667, December, 1998. 相似文献
20.
Synthesis of 4H-1,4-benzothiazines containing thiazole ring system is reported by condensation of substituted 2-amino-benzenethiols
with N-(substituted benzothiazol-2-yl)-3-oxo-butyr-amides in the presence of DMSO. 相似文献