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1.
Tommy J. Mccord Sherrel C. Smith David L. Tabb Alvie L. Davis 《Journal of heterocyclic chemistry》1981,18(5):1035-1039
The cis- and trans-3-amino-3,4-dihydro-1-hydroxy-4-methylcarbostyrils (Ia and Ib) were synthesized by catalytic hydrogenation of erythro- and threo-α-amino-β-(o-nitrophenyl)butyric acid hydrochlorides, IIIa and IIIb, respectively, under acidic conditions. The free bases of IIIa and IIIb were catalytically hydrogenated under neutral conditions to yield the erythro- and threo-α-amino-β-(o-aminophenyl)butyric acids (VIa and VIb), which were converted by acidification to their corresponding lactams, cis- and trans-3-amino-3,4-dihydro-4-methylcarbostyrils, IIa and IIb. The erythro and threo isomers of α-amino-β-(o-nitrophenyl)-butyric acid were prepared and separated by liquid chromatography via a diastereomeric mixture of (V) of methyl α-acetamido-β-(o-nitrophenyl)butyrates. The configurations and conformational assignments of the cyclic hydroxamic acids Ia and Ib were first established by analysis of the proton nmr spectra. In turn, the configurations of the o-nitroaromatic amino acids IIIa and IIIb were assigned as well as the other structurally related compounds (VIa, VIb, IIa and IIb) derived therefrom. 相似文献
2.
Tze-Ming Chan R. Friary H. Jones J. H. Schwerdt V. Seidl A. S. Watnick S. M. Williams 《Journal of heterocyclic chemistry》1990,27(4):1135-1142
1-Phenylmethyl- and 1-(4-methoxyphenylmethyl)-5-chloro-1,2,3-triazole-4-carbonyl chlorides acylated the pyrrolidine enamines of cyclopentanone and cyclohexanone, and the resulting enaminones underwent transaminations with aryl amines under acidic conditions. The products then cyclized under basic conditions to linearly fused, tricyclic 3-phenylmethyl- and 3-(4-methoxyphenylmethyl)-4-aryl-8-oxo-4,5,6,7-tetrahydrocyclopenta[6]-1,2,3-triazolo[4,5-e]pyridines, and to 5,6,7,8-tetrahydro-4-aryl-3H-1,2,3-triazolo[4,5-b]quinolin-9(4H)-ones. Similar transaminations afforded the related 8-phenyl- and 8-(3-chlorophenyl)-1,5,7,8-tetrahydro-1-(phenylmethyl)-4H-thieno[3,4-e]-1,2,3-triazolo[4,5-b]pyridin-4-ones. Phase-transfer and catalytic hydrogenolyses of some of these intermediates furnished 4-aryl-8-oxo-4,5,6,7-tetrahydrocyclopenta[b]-1,2,3-triazolo[4,5-e]pyridines and 4-aryl-5,6,7,8-tetrahydro-3H,2,3-triazolo[4,5-b]quinoline-9-(4H)-ones. The 3-(4-methoxyphenylmethyl)-4-aryl intermediates were sterically crowded. Two protons from the methoxyphenylmethylphenylmethylgroups were dramatically shielded because of anisotropic effects exerted by the 4-aryl substituents. 相似文献
3.
Silvia Kováčová Lucia Kováčiková Margita Lácová Andrej Boháč Marta Sališová 《Chemical Papers》2010,64(6):806-811
Perkin condensation with subsequent intramolecular lactonisation as one pot syntheses of 2-(2-oxo-2H-chromen-3-yl)acetic acids VIIa-Xa has been studied. The required acids VIIa-Xa were prepared as precursors of recently discovered compounds possessing antineoplastic activities. Syntheses of VIIa-Xa were carried out using para substituted 2-hydroxybenzaldehydes II-VI, succinic acid anhydride, sodium succinate under thermal or microwave conditions. Significant shortening of the reaction
time under microwave irradiation was observed (18–50 min instead of 1.5–5 h of heating). Microwave assisted reactions proceeded
more smoothly to give higher yield of the required products VIIa-Xa (31–61 %) compared to those under classical thermal conditions e.g. 21.8 % for IXa (Hurenkamp et al., 2007). Seven reaction by-products were isolated and determined as 2H,2′H-3,3′-bichromene-2,2′-diones VIIb-Xb and (E)-3-(2-hydroxystyryl)-2H-chromen-2-ones VIIc-IXc. 相似文献
4.
Alvie L. Davis David L. Tabb Janet K. Swan Tommy J. Mccord 《Journal of heterocyclic chemistry》1980,17(7):1405-1408
The 3-methyl and 4-methyl derivatives of 3-amino-3,4-dihydro-1-hydroxycarbostyril were synthesized by the reductive cyclization of α-methyl-β-(o-nitrophenyl)alanine and α-amino-β-(o-nitrophenyl)butyric acid hydrohalides, respectively, under conditions of catalytic hydrogenation in acidic solution. The free bases of the latter two o-nitroaromatic amino acids were also catalytically hydrogenated under neutral conditions to yield the respective α-methyl-β-(o-aminophenyl)alanine and α-amino-β-(o-aminophenyl)butyric acid which were converted to the corresponding lactams, 3-methyl- and 4-methyl-3-amino-3,4-dihydrocarbostyrils. α-Methyl-β-(o-nitrophenyl)alanine was obtained by acid hydrolysis of 5-methy)-5-(o-nitrobenzyl)hydantoin which was prepared by treatment of o-nitrophenylacetone with potassium cyanide and ammonium carbonate. α-Amino-β-(o-nitrophenyl)butyric acid was synthesized by condensation of α-bromo-o-nitroethylbenzene with diethyl acetamidomalonate, followed by acid hydrolysis of the condensation product. The 4-methylated compounds were obtained as synthetic mixtures of two diasteromeric racemates in nearly the same amounts as shown by nmr spectral analysis. Unlike the demethylated parent compound, 3-amino-3,4-dihydro-1-hydroxycarbostyril, neither the 3-methyl nor 4-methyl analog was found to possess any antibacterial activity. 相似文献
5.
Zbigniew Malinowski Aleksandra K. Szcześniak Wanda Pakulska Dariusz Sroczyński Elżbieta Czarnecka Jan Epsztajn 《合成通讯》2014,44(24):3572-3581
A series of new alkyl, tosyl, acetyl, and tert-butoxycarbonyl derivatives of 2-(2-aminoethyl)-phthalazinones were efficiently synthesized by reaction of lactams with N-Boc-, N-acetyl-, or N,O-ditosyl derivatives of N-methylethanolamine in the presence of MeONa or under Mitsunobu reaction conditions. Selected compounds were converted into corresponding 2-[2-(methylamino)ethyl]phthalazinones in good yields. 相似文献
6.
Richard A. Newmark Ramendra N. Majumdar 《Journal of polymer science. Part A, Polymer chemistry》1988,26(1):71-77
Homopolymers of myrcene and farnesene were prepared anionically in pure cyclohexane. The microstructure, determined from an analysis of the 13C-NMR spectrum and spin-lattice relaxation times, indicates the polymers are at least 85% cis-1,4, 10% cis-3,4, and under 3% trans-1,4. 相似文献
7.
微波促进下3-(2-苯并呋喃基)-4-氨基-5-巯基-1,2,4-三唑 总被引:1,自引:0,他引:1
微波辐射条件下, 首先由2-苯并呋喃甲酰肼依次与二硫化碳和水合肼反应合成3-(2-苯并呋喃基)-4-氨基-5-巯基- 1,2,4-三唑, 进一步在微波辐射条件下由4-氨基-5-巯基-1,2,4-三唑分别与芳甲酸/芳氧基乙酸、α-溴代苯乙酮及芳醛反应以较高产率制得了相应的1,2,4-三唑并[3,4-b]-1,3,4-噻二唑、1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪及4-芳亚甲基亚胺基-5-巯基-1,2,4-三唑. 产物结构经IR, 1H NMR, MS及元素分析进行了表征. 相似文献
8.
Glycosylation of 3β,6α,12β-trihydroxy-20R,25-epoxydammarane (panaxatriol) and its 3-, 6-, and 3,6-di-O-acetyl derivatives was studied under Koenigs—Knorr conditions. Panaxatriol 3-, 6-, and 12-O-β-Dglucopyranosides were synthesized for the first time. 相似文献
9.
AbstractThe building block synthon, 1-(4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethan-1-one was efficiently synthesized by Biginelli reaction of 1,3-diphenyl-1H-pyrazole-4-carbaldehdye, acetylacetone, and thiourea and submitted to react with ethyl chloroacetate and chloroacetyl chloride under different conditions to afford some N-heterocycles integrated with pyrazole scaffold. Hydrazinolysis of the pyrimidinethione was studied under different conditions. The insecticidal activity for these compounds, DFT calculations, and docking were run and discussed. Some of them exhibited 100% mortality against Nilaparvata lugens and Mythimna separata. 相似文献
10.
2,2-Dimethyl-3-(2-methyl-3-indolyl)cyclopropylacetic acid, its amide and esters, and the corresponding alcohol, viz., the product of ester reduction by LiAlH4, were synthesized. The chemoselectivity of N- and O-alkylation of these compounds was studied. Selective monoalkylation at the nitrogen atom of the heterocycle, O-alkylation to the side chain, or dialkylation at both nucleophilic sites can be carried out under conditions of phase-transfer catalysis. The N-acylation at the indole fragment of nitrile of this acid occurs only under the Vilsmeier—Haak formylation conditions. 相似文献
11.
Summary Direct resolution of four stereoisomers of the related compound of diltiazem hydrochloride, namely desacetyl diltiazem hydrochloride, was studied by both normal and reversed-phase chiral HPLC. The four stereoisomers were completely resolved on a Chiralcel OF column. The technique developed was applied to a chiral inversion study of desacetyl diltiazem hydrochloride. This inversion was observed neither in the solid state, in aqueous solution at 100°C for 3 h nor under visible light for 10h, but was observed in aqueous solution under UV irradiation.The (+)-(2S, 3S)-cis-desacetyl diltiazem hydrochloride degraded with a half-life of 1.9 h in aqueous solution under UV and epimerized to (+)-(2R, 3S)-trans-desacetyl diltiazem hydrochloride. Similarly, (+)-(2S, 3S)-cis-desacetyl diltiazem hydrochloride degraded about three times faster than diltiazem hydrochloride. Reverse epimerization of (+)-(2R, 3S)-trans-desacetyl diltiazem hydrochloride to (+)-(2S, 3S)-cis-desacetyl diltiazem hydrochloride was not observed.The overall degradation was the result of two competitive processes, the epimerization and the decomposition of the benzothiazepin ring. The degradation and epimerization rate of (+)-(2S, 3S)-cis-desacetyl diltiazem hydrochloride in solution under UV depended upon the solvent, the aqueous pH, and concentration. 相似文献
12.
Heterocyclization reactions of azinoisocyanates. Synthesis of 2H-1,2,4-triazol-3(4H)-one derivatives
Kee-Jung Lee Jin Lyang Kim Mun Ki Hong Jung Yong Lee 《Journal of heterocyclic chemistry》1999,36(5):1235-1240
The reaction of 1-aminoethylidenehydrazones 9 with di-tert-butyl dicarbonate and 4 -dimethylaminopyridine led to the corresponding azinoisocyanates 10 , which underwent thermal rearrangement under the reaction conditions to give 4-(tert-butoxycarbonyl)-5-methyl-2H-1,2,4-triazol-3(4H)-ones 14 . However, amidrazone 17 gave 2-(2-tert-butoxycarbonyloxy-2-phenyl)ethyl-4-(tert-butoxycarbonyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one 22 and N-aziridinyliminocarbamate 18 under the similar conditions. 相似文献
13.
Contrary to other N-(pyridyl)nitramines, the title compound cannot be rearranged to 3-amino-2-nitropyridine or other isomers. Hypothetical products
of its transformation under influence of concentrated sulphuric acid, viz. 3-hydroxypyridine, 3,3′-azoxypyridine and 3,3′-azopyridine,
were obtained from 3-nitro- and 3-aminopyridine in oxidation and reduction reactions. N-(3-Pyridyl)nitramine was prepared and rearranged in concentrated sulphuric acid. 3-Hydroxypyridine and 3,3′-azoxypyridine
were isolated from the reaction mixture, other products were identified by the HPLC and GCMS methods. The results indicate
that N-(3-pyridyl)hydroxylamine is an intermediate formed from N-(3-pyridyl)nitramine under the influence of concentrated sulphuric acid. The reaction path, leading to the final products,
is discussed in context of the mechanism of nitramine rearrangement. 相似文献
14.
Ian F. Cottrell David Hands Peter G. Houghton Guy R. Humphrey Stanley H. B. Wright 《Journal of heterocyclic chemistry》1991,28(2):301-304
A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described. The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used. Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35–40° to give 1H-1,2,3-triazoles usually in good yield. Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively. Benzyl methyl ketone reacted to give a 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react. Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate. 相似文献
15.
C. J. Shishoo M. B. Devani G. V. Ullas S. Ananthan V. S. Bhadti 《Journal of heterocyclic chemistry》1985,22(3):825-830
Synthesis of 2-(2-arylvinyl)thienopyrimidines, by the acid catalyzed condensation of nitriles with thiophene o-aminocarbonyl compounds, the condensation of aldehydes with thiophene o-aminoamides, the base catalyzed condensation of aldehydes with 2-methylthienopyrimidines and by the Wittig condensation of 2-thieno-pyrimidinylmethylphosphonium salts with aldehydes is described. Isomeric 5-methyltriazolothienopyrimidines were found to react, under basic condition, with aldehydes yielding 5-(2-arylvinyl)triazolo[2,3-c]thieno-pyrimidines. While 5-styryltriazolo[4,3-c] isomers resisted acid catalysed isomerization, they were found to isomerize to triazolo[2,3-c]pyrimidines under base catalysis. 相似文献
16.
Matyushenkov E. A. Churikov D. G. Sokolov N. A. Kulinkovich O. G. 《Russian Journal of Organic Chemistry》2003,39(4):478-485
Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2-(trans-1-propenyl)tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxytitanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp). 相似文献
17.
Shuyin Liu Guihua Xiong Fengxi Li Shushu Wei Zhi Wang 《Green Chemistry Letters and Reviews》2016,9(4):190-195
(S)-3-hydroxy-3-(2-thienyl) propanenitrile, which is the key chiral building block for the synthesis of (S)-duloxetine, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically enhanced under ultrasound irradiation. Under optimum reaction conditions (solvent: n-hexane, ultrasound power: 150?W, aw: 0.33, temperature: 40°C), Pseudomonas sp. lipase exhibited an excellent catalytic performance (enzyme activity: 81.5?μmol?g?1?min?1, E-value: 65.4). The reaction achieved its equilibrium in approximately 7?h with a conversion of 53.9% and high enantiopurity (99% ee) of (S)-3-hydroxy-3-(2-thienyl) propanenitrile could be obtained. 相似文献
18.
Mario Bruzzone Antonio Carbonaro 《Journal of polymer science. Part A, Polymer chemistry》1985,23(1):139-157
Solutions of crystalline, high-melting trans-1,4 polybutadiene (trans-PB), trans-1,4 mix 1,2 butadiene-piperylene copolymer (BPC, low piperylene content), and isotactic trans-1,4 piperylene (trans-PP) were partly hydrochlorinated under mild conditions with gaseous HCl. Glass transition and melting temperatures were strongly affected by the addition of HCl. Several hydrochlorinated trans-PB and -BPC were semicrystalline or amorphous elastomers, susceptible to reversible crystallization when stretched. The straininduced crystallinity was similar to that shown by trans-polybutadiene sequences, particularly in the form that is unstable in bulk at room temperature (form II). The addition of HCl to the asymmetric double bond in trans-PP occurs in a stereoselective way, according to 13C-NMR. under the experimental conditions of the present study the occurrence of side reactions was observed; these reactions decrease the polymer unsaturation to a lower level than that calculated by the amount of HCl added to the polymer. 相似文献
19.
1,3,7,9,11,12,14-Heptazapentacene-2,4,8,10(14H,3H,9 H,12H)-tetraones (mixed flavins) were synthesized by the cyclization of 1,5-dihydro-8-[N-alkyl-N-(5-nitrouracil-6-yl)]-amino-5- deazaflavins with the Vilsmeier reagent. The mixed flavins oxidized alcohol under neutral conditions in sunlight. 相似文献
20.
Masatoshi Sakae Masanori Katsurada Mayumi Watanabe Fumio Yoneda Sadao Nishigaki Toshimasa Ishida 《Journal of heterocyclic chemistry》1997,34(1):157-160
The reaction of 2-bromoethylamine 1 with methylisothiocyanate 2 under mild condition gave 2-methyl-amino-2-thiazoline 3 as the major product together with two kinds of byproducts, 3-(N-methylthiocar-bamoyl)-2-methyliminothiazolidine 4 and N,N′-dimethyl-N-(2-thiazolin-2-yl)thiourea 5. Thermal isomer-ization of 5 to 4 was observed. The structures of the byproducts were confirmed by X-ray crystallography. 相似文献