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1.
2-Mercapto-3-amino-5-chloropyridine reacts with phenacyl halides to yield 2-phenacylmercapto-3-amino-5-chloropyridines and 2-aryl-7-chloro-3H-pyrido[2, 3-b][1, 4]thiazines.For part V, See [11]. 相似文献
2.
Kristjan S. Gudmundsson Jack M. Hinkley Michael S. Brieger John C. Drach Leroy B. Townsend 《合成通讯》2013,43(5):861-870
An efficient large scale synthesis of 2-amino-4-chloropyridine (3) has been achieved through a modification of existing literature procedures. Compound 3 was used to prepare the previously unreported 2-amino-4,5-dichloropyridine (4). The known 2-amino-3,4-dichloropyridine (5) and 2-amino-3,4,5-trichloropyridine (6) were prepared from 3 by new routes and in higher yields than previously reported. 相似文献
3.
1-and 3-Substituted imidazo[4,5-b]pyridin-2-ones were synthesized by heating equimolar amounts of 3-amino-2-chloropyridine or 2-chloro-3-methylaminopyridine, urea, and the corresponding arylamine at 150–210°C. The reaction of 3-amino-2-chloropyridine with urea and p-phenylenediamine or p,p′-diaminobiphenyl at a ratio of 2:2:1 under analogous conditions gave 1,4-bis-(2-oxoimidazo[4,5-b]pyridin-3-yl)benzene or 1,4-bis(2-oxoimidazo[4,5-b]pyridin-3-yl)biphenyl, respectively. 相似文献
4.
A. M. Demchenko K. G. Nazarenko A. P. Andrushko D. V. Fediyuk A. N. Krasovsky L. M. Yagupolsky 《Chemistry of Heterocyclic Compounds》2003,39(7):965-969
A synthesis is reported for -bromo-4-difluoromethylthioacetophenone and the conditions for the condensation of this compound with 2-aminothiazole, 2-amino-5-chloropyridine, 2-amino-4,5-dihydro-3H-pyrrole, benzimidazoline-2-thione, oxadiazoline-2-thione, and thiourea were studied. S- and N-substituted azaheterocycles containing the 4-(difluoromethylthio)phenyl fragment were synthesized and characterized. 相似文献
5.
T. V. Ghochikyan V. S. Harutyunyan M. A. Samvelyan E. V. Harutyunyan 《Russian Journal of Organic Chemistry》2014,50(10):1456-1464
Alkylation of 3-acetyl-5-(alkoxymethyl)tetrahydrofuran-2-ones gave 3-acetyl-5-(alkoxymethyl)-tetrahydrofuran-2-ones containing various substituents in position 3 of the heterocycle. Bromination of the latter afforded 3-(bromoacetyl) derivatives which reacted with various nucleophiles to produce derivatives containing benzimidazole, 2-amino-1,3-thiazole, 3-chloropyridine, and 3,5-dibromopyridine fragments together with the butanolide ring. 相似文献
6.
A high-yielding and practical synthesis of 6-chloro-2-(chloromethyl)-thiazolo[5,4-b]pyridine starting from 2-amino-5-chloropyridine has been accomplished in a sequence of five steps. 相似文献
7.
The 2′-deoxyisoguanosine ( 1 ) was synthesized by a two-step procedure from 2′-deoxyguanosine ( 5 ). Amination of silylated 2′-deoxyguanosine yielded 2-amino-2′-deoxyadenosine ( 6 ) which was subjected to selective deamination of the 2-NH2 group resulting in compound 1 . Also 2′,3′-dideoxyisoguanosine ( 2 ) was prepared employing the photo-substitution of the 2-substituent of 2-chloro-2′,3′-dideoxyadenosine ( 4 ). The latter was synthesized by Barton deoxygenation from 2-chloro-2′-deoxyadenosine ( 3 ) or via glycosylation of 2,6-dichloropurine ( 12 ) with the lactol 13 . Compound 1 was less stable at the N-glycosylic bond than 2′-deoxyguanosine ( 5 ). The dideoxynucleoside 2 was deaminated by adenosine deaminase affording 2′,3′-dideoxyxanthosine ( 17 ). 相似文献
8.
A facile way has been developed to provide a series of novel chiral N-(4-(piperidin-1-yl)pyridin-2-yl)amide derivatives as potential stereoselective catalysts. The key intermediate, 2-amino-4-piperidinyl pyridine, was obtained by nucleophilic substitution of 2-amino-4-chloropyridine with piperidine in good yields (up to 96%). The total control of enantioselectivity was obtained for the synthesis of L-proline and (R)-1,1′-bi(2-naphthol) derivatives. 相似文献
9.
The photocatalysed reaction of four selected organic systems, namely dichlone (1), 2-amino-5-chloropyridine (2), benzoyl peroxide (3) and 3-chloro perbenzoic acid (4), has been investigated in an acetonitrile/water mixture in the presence of titanium dioxide and oxygen. An attempt has been
made to identify the products formed during the photo-oxidation process using the GC/MS analysis technique. The photolysis
of dichlone (1) leads to the formation of phthalic anhydride (11) and 1H-indene-1,2,3-trione (10), whereas 2-amino-5-chloropyridine (2) gave rise to 2,2′-diamino bipyridyl (14), 2-pyridinamine (16), 2-hydroxy-5-chloropyridine (18), bipyridyl (19) and 2-amino bipyridyl (21). The photolysis of benzoyl peroxide (3) yielded a mixture of products such as benzoic acid (24), biphenyl (27), biphenyl-4-carboxylic acid (29) and benzoic acid phenyl ester (30). Two intermediate products, as 3-chlorobenzaldehyde (35) and hydroxyl added 3-chlorobenzaldehyde (33), have been identified in the case of 3-chloro perbenzoic acid (4). The products have been identified by comparing the molecular ion and mass fragmentation peaks of the products with those
reported in the GC-MS library. A probable mechanism for the formation of the products has been proposed. 相似文献
10.
《Journal of Coordination Chemistry》2012,65(6):863-875
The reaction of CuX2 (X = Cl or Br) with 3-amino-2-chloropyridine in aqueous acids (HX; X = Cl or Br) yields bis(3-amino-2-chloropyridinium)tetrachlorocuprate(II) and bis(3-amino-2-chloropyridinium)tetrabromocuprate(II). Both compounds have been characterized by IR, powder X-ray diffraction, single-crystal X-ray diffraction and temperature dependent magnetic susceptibility. The compounds are isomorphous and exhibit weak antiferromagnetic interactions. 相似文献
11.
A synthesis of 6-aminonicotinic acid by electrochemical hydrogenation of 5-chloro-2-nitropyridine and electrochemical carboxylation of 2-amino-5-chloropyridine at a cathode surface in the presence of sulphuric acid and carbon dioxide in a dimethylformamide (DMF) solution at an apparent current density of 10 mA/cm2 using an undivided cell with good yields is reported. 相似文献
12.
The hydrochlorides of the title compounds are obtained in moderate yields by refluxing 2-chloro-3-aminopyridine or 3-amino-4-chloropyridine, respectively, with an alkyl. Aralkyl-, or aryl isothiocyanate in absolute ethanol solution. A proof is presented that the 2-aminothiazolopyridine hydrochloride and not the isomeric o-chloropyridylthiourea is the product of this reaction. The free-bases may be obtained from the hydrochlorides with aqueous sodium bicarbonate. A mechanism for the formation of the thiazole ring is briefly considered. The interactions of 2-chloro-3-aminopyridine with l-substituted-5-mereapto-1H-tetrazoles are also described. 相似文献
13.
Karen Wright Marco CrismaClaudio Toniolo Roland TörökAntal Péter Michel WakselmanJean-Paul Mazaleyrat 《Tetrahedron letters》2003,44(16):3381-3384
Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)-α-methylbenzylamine, NaBH3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3S,4S) and (3R,4R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates. 相似文献
14.
N. S. Prostakov N. N. Mikheeva Dkharvar Pkhal'gumani 《Chemistry of Heterocyclic Compounds》1967,3(2):539-540
1,2,5-Trimethylpiperid-4-one is used to prepare 1, 2, 5-trimethyl-4-aminopiperidine, which is then converted to 1, 2, 5-trimethyl-4-(diethylaminoacetylamino)piperidine. Amination of 2, 5-dimethyl-4-phenylpyridine is effected, and 3, 6-dimethyl-4-phenyl-2-aminopyridine is thereby obtained. 相似文献
15.
A capillary electrophoretic enantioselective method with UV detection was developed and validated for the simultaneous quantification of zopiclone enantiomers and its impurities, zopiclone-N-oxide enantiomers, and 2-amino-5-chloropyridine, in tablets. The analytes were extracted from the tablets using ACN and were separated in an uncoated fused-silica capillary (50 μm, 42 cm effective length, 50 cm total length) using 80 mM sodium phosphate buffer pH 2.5 and 5 mM carboxymethyl-β-cyclodextrin as running buffer. The analytes and the internal standard (trimethoprim) were detected at 305 and 200 nm, respectively. A voltage of 27 kV was applied and the capillary temperature was maintained at 25°C. All enantiomers were analyzed within 8 min and linear calibration curves over the concentration range of 0.4-0.8 mg mL?1 for each zopiclone enantiomer, 0.8-1.6 μg mL?1 for 2-amino-5-chloropyridine and 0.4-0.8 μg mL?1 for each zopiclone-N-oxide enantiomer were obtained. The coefficients of correlation obtained for the linear curves were greater than 0.99. The intra-day and inter-day accuracy and precision were lower than 2% for all analytes. This validated method was employed to study the degradation and racemization of zopiclone under stress conditions. This application demonstrated the importance of a stability-indicating assay method for this drug. 相似文献
16.
Max M. Boudakian 《Journal of fluorine chemistry》1981,18(4):497-506
The isolation and stabilization of elusive 4-fluoropyridine as the hydrochloride salt (54% yield) from fluorodediazoniation of 4-aminopyridine in anhydrous hydrogen fluoride (AHF) is described. Unlike the low yields (0–13%) recently reported from the chlorodediazoniation of 2,6-diaminopyridine and 3-halo-2,6-diaminopyridine, fluorodediazoniation gave high yields (49–62%) of the corresponding 2,6-difluoropyridines. In contrast, benzene analogs, i.e. -phenylenediamine and 4-chloro--phenylenediamine, form only tars under similar fluorination conditions. Vicinal aminohalopyridines, e.g. 3-amino-2-chloropyridine and 2-amino-3,5-dichloropyridine give the corresponding fluorohalopyridine in 49–89% yield. Again, the benzene analogs, i.e. -chloroaniline and 2,4-dichloroaniline, resist fluorination. 相似文献
17.
Pentosidine, a biologically important advanced glycation endproduct, has been accessed in a rapid, high-yielding manner. The synthesis was accomplished via a six-step sequence starting with 3-amino-2-chloropyridine and features a palladium-catalyzed tandem cross-coupling/cyclization to construct the imidazo[4,5-b]pyridine core. 相似文献
18.
The reaction of (3-amino-6-chloro-2-pyridylmercapto)oxalacetic ester with ammonia, benzylamine, morpholine, and piperidine yielded amides, while the reaction of the ester with hydrazine hydrate gave [2-(ethoxycarbonylmethylthio)-3-pyridyl]oxamic acid hydrazide. The benzylamide and morpholide of this acid were obtained by treatment of 2-chloro-6-hydroxy-6,7-di(ethoxycarbonyl)dihydropyridothiazine with the appropriate amines. The reaction of 2-mercapto-3-amino-6-chloropyridine with chlorooxalacetic ester in the presence of alkali yielded potassium [2-(ethoxycarbonylmethylthio)-3-pyridyl]oxamate.See [1] for communication XXI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1502–1505, November, 1971. 相似文献
19.
20.
The reaction of 2-mercapto-3-ureido-6-chloropyridine with chlorodibenzoylmethane in the presence of alkali leads to 2-(benzoylmethylthio)-3-benzamido-6-chloropyridine,
whereas the reaction in the absence of alkali leads to 2-chloro-6-phenyl-7-benzoylpyrido[2,3-b] [1,4]thiazine. Under similar
conditions 2-(diacetylmethylthio)-3-ureido-6-chloropyridine, 2-(acetylmethylthio)-3-ureido-6-chloropyridine, and 2-chloro-6-methyl-7-acetylpyrido[2,3-b][1,4]thiazine
were obtained from 2-mercapto-3-ureido-6-chloropyridine and chloroacetylacetone. Treatment of 2-(diacetylmethylthio)-3-ureido-6-chloropyridine
with alcoholic alkali leads to 2-(acetylmethylthio)-3-ureido-6-chloropyridine. 2-Chloro-6-phenyl-7-acetylpyrido-[2,3-b] [1,4]thiazine
and 2-(benzoylmethylthio)-3-ureido-6-chloropyridine are formed in the reaction of 2-mercapto-3-ureido-6-chloropyridine with
chlorobenzoylacetone in the presence of an equimolar amount of alkali, while 2-(benzoylmethylthio)-3-acetamido-6-chloropyridine
is formed when excess alkali is used.
See [1] for communication 37.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 787–790, June, 1980. 相似文献