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1.
D. A. Skladchikov A. A. Fatykhov R. R. Gataullin 《Russian Journal of Organic Chemistry》2012,48(3):383-386
Heating of the bromination product of 4-methyl-3,6-dihydro-2H-pyran with 4-toluidine or 2-bromo-4-methylamiline in triethylamine gave 4-methyl-N-(4-methylphenyl)- and N-(2-bromo-4-methylphenyl)-4-methyl-3,6-dihydro-2H-pyran-3-amines which were converted into the corresponding amides by reaction with bromo- or chloroacetyl chloride. 1-{4a,6-Dimethyl-4a,9a-dihydropyrano[3,4-b]indol-9(1H)-yl} ethanone was synthesized in good yield by heating N-(2-bromo-4-methylphenyl)-N-(4-methyl-3,6-dihydro-2Hpyran-3-yl)acetamide in boiling toluene in the presence of palladium(II) acetate, triphenylphosphine, copper(II) acetate,
triethylamine, and potassium carbonate. 相似文献
2.
D. A. Skladchikov K. Yu. Suponitskii R. R. Gataullin 《Russian Journal of Organic Chemistry》2013,49(10):1486-1490
The reaction of 2-iodo-2,4-dimethylaniline with 3,4-dibromo-4-methyltetrahydro-2H-pyran, followed by treatment with acetyl bromide or 4-nitrobenzoyl chloride, gave syn- and anti-atropisomers of N-(2-iodo-4,6-dimethylphenyl)-N-(4-methyl-3,6-dihydro-2H-pyran-3-yl)acetamide and N-(2-iodo-4,6-dimethylphenyl)-N-(4-methyl-3,6-dihydro-2H-pyran-3-yl)-4-nitrobenzamide. Heating of the acetamide derivative with palladium(II) acetate in the presence of copper(II) acetate and N,N,N′,N′-tetramethylethane-1,2-diamine resulted in heterocyclization to N-acetyl-4a,6,8-trimethyl-1,4a,9,9a-tetrahydropyrano[3,4-b]indole. 相似文献
3.
V. V. Tkachev Yu. A. Sayapin I. V. Dorogan V. S. Gorkovets A. A. Kolodina V. N. Komissarov G. V. Shilov S. M. Aldoshin V. I. Minkin 《Russian Journal of Organic Chemistry》2013,49(3):439-445
Acid-catalyzed reaction of 6,10a-dihydroxy-3,4a,7,9-tetra(tert-butyl)-1,2,4a,10a-tetrahydrodibenzo-[b,e][1,4]dioxine-1,2-dione with 4-chloro-2,7,8-trimethylquinoline gave previously unknown 3,6,8-tri-tert-butyl-3-[2-tert-butyl-5-(4-chloro-7,8-dimethylquinolin-2-yl)-4-hydroxy-3-oxopenta-1,4-dien-1-yl]-5-hydroxy-1,4-benzodioxin-2-one whose structure was determined by X-ray analysis. The energy and structure parameters of possible isomers of the product in the gas phase and in solution were estimated by PBE0/6-31G** quantum-chemical calculations. 相似文献
4.
Giuseppe Daidone Salvatore Plescia Jole Fabra 《Journal of heterocyclic chemistry》1980,17(7):1409-1411
Thermal decomposition of the diazonium sulfate derived from N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-aminobenzamide afforded products formulated as 1-phenyl-3-methyl[2]benzopyrano[4,3-c]pyrazol-5-one (yield 10%), 1,4-dimethyl-3-phenylpyrazolo[3,4-c]isoquinolin-5-one (yield 10%), N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-hydroxybenzamide (yield 8%) and 4′-hydroxy-2,3′-dimethyl-1′-phenylspiro[isoindoline-1,5′-[2]-pyrazolin]-3-one (yield 20%). Decomposition of the diazonium sulfate derived from N-methyl-(1,3-diphenylpyrazol-5-yl)-2-aminobenzamide gave products formulated as 7,9-dimethyldibenzo[e,g]pyrazolo[1,5-a][1,3]-diazocin-10-(9H)one (yield 8%), 4-methyl-1,3-diphenylpyrazolo[3,4-c]isoquinolin-5-one (yield 7%) and 4′-hydroxy-2-methyl-1′,3′-diphenylspiro[isoindoline-1,5′-[2]pyrazolin]3-one (yield 10%). The spiro compounds 6a,b underwent thermal and acid-catalysed conversion into the hitherto unknown 2-benzopyrano[4,3-c]pyrazole ring system 7a,b in good yield. Analytical and spectral data are presented which supported the structures proposed. 相似文献
5.
Kinga Wzgarda-Raj Justyna Dominikowska Sławomir Wojtulewski Agnieszka J. Rybarczyk-Pirek 《Acta Crystallographica. Section C, Structural Chemistry》2023,79(2):52-60
The results of the X-ray structure analysis of three novel 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine cocrystals are presented. These are 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine–2,4,6-tribromophenol (1/2), C12H8N6·2C6H3Br3O, 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine–isonicotinic acid N-oxide (1/2), C12H8N6·2C6H5NO3, and 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine–4-nitrobenzenesulfonamide (1/1), C12H8N6·C6H6N2O4S. Special attention is paid to a conformational analysis of the title tetrazine molecule in known crystal structures. Quantum chemistry methods are used to compare the energetic parameters of the investigated conformations. A structural analysis of the hydrogen and halogen bonds with acceptor aromatic tetrazine and pyrazine rings is conducted in order to elucidate factors responsible for conformational stability. 相似文献
6.
Competition of Endoperoxide and Hydroperoxide Formation in the Reaction of Singlet Oxygen with Cyclic, Conjugated Dienes Rose-bengal-sensitized photooxygenation of (?)-(R)-α-phellandrene ( 1 ) in MeOH at room temperature yielded a complex mixture of products, contrary to previous reports describing cis-(3S, 6R)-epidioxy-p-menthene ( 2 ) and trans-(3R, 6S)-epidioxy-p-menthene ( 3 ) as the only products. The mixture was separated by prep. HPLC (silica gel, pentane/Et2O 9:1). Besides the known endoperoxides 2 (yield 39%) and 3 (26%), all those hydroper-oxides, which can be deduced from an ene reaction of 1O2 with 1 , were isolated, i.e. 4β-p-mentha-2,5-dien-1β-yl hydroperoxide ( 4 ) (14%), 4β-p-mentha-2,5-dien-1α-yl hydroperoxide ( 5 ) (9%), (2R, 4R)-p-mentha-1(7), 5-dien-2-yl hydroperoxide ( 6 ) (2,1%), (2S, 4R)-p-mentha-1(7),5-dien-2-yl hydroperoxide ( 7 ) (1,5%) and (1R)-p-mentha-3,6-dien-yl hydroperoxide ( 8 ; 1,5%; Scheme 1). Furthermore, the constant cis/trans ratio for all diastereoisomeric pairs ( 2 / 2 , 4 / 2 , 6 / 2 ) was striking. With the help of the two possible conformers 1a and 1b of the starting material a model of a common first step for endoperoxide as well as for hydroperoxide formation is developed. A photooxygenation at ?50° supports this model. The absolute value of the cis/trans ratio changes in the same way for the endoperoxides and the hydroperoxides. 相似文献
7.
Choudhary MI Sultan S Khan MT Yasin A Shaheen F Atta-ur-Rahman 《Natural product research》2004,18(6):529-535
Fermentation of (+)-androst-4-ene-3,17-dione (1) with Curvularia lunata for 10 days yielded five oxidative and reductive metabolites, androsta-1,4-diene-3,17-dione (2), 17beta-hydroxyandrosta-1,4-dien-3-one (3), 11alpha-hydroxyandrost-4-ene-3,17-dione (4), 11alpha,17beta-dihydroxyandrost-4-en-3-one (5) and 15alpha-hydroxyandrosta-1,4-dien-17-one (6). The structures of these metabolites were elucidated on the basis of spectroscopic techniques. These microbially transformed products were assayed against the clinically important enzymes, tyrosinase and prolyl endopeptidase. 相似文献
8.
T. Yu. Baranova O. N. Zefirova A. M. Banaru V. N. Khrustalev A. A. Ivanova A. A. Ivanov N. S. Zefirov 《Russian Journal of Organic Chemistry》2012,48(4):552-555
Crystallization of N-[(8R)-2-methoxy-5,6,7,8,9,10-hexahydro-6,9-methanocyclohepta[b]indol-8-yl]acetamide was accompanied by oxidation at the C5a–C10a bond with formation of N-[(5S)-10-methoxy-2,8-dioxo-1,2,3,4,5,6,7,8-octahydro-3,6-methano-1-benzazecin-5-yl]acetamide whose structure was determined by
X-ray analysis. Docking of this compound into melatonin-binding pocket of MT1A receptor was simulated by computer-assisted molecular modeling. 相似文献
9.
An efficient and convenient transformation of α-haloketones to α-hydroxyketones using cesium formate
Fung Fuh Wong Po-Wei Chang Hui-Chang Lin Bang-Jau You Jiann-Jyh Huang Shao-Kai Lin 《Journal of organometallic chemistry》2009,694(21):3452-3455
A new safe and convenient transformation has been developed. In the presence of cesium formate in dry MeOH solution, α-haloketones underwent direct conversion reaction to afford α-hydroxyketone in excellent yields. Furthermore, this methodology can be extended and applied in 2-chloro-N-(1,3-diphenyl-1H-pyrazol-5-yl)acetamide, 2-chloro-N-(2,6-dimethylphen-yl)acetamide, 1-(bromomethylsulfonyl)benzene, and N-(bromomethyl)phthalimide to give the corresponding products in moderate to excellent yields. 相似文献
10.
Rita Vaickelionienė Vytautas Mickevičius Gema Mikulskienė Maryna Stasevych Olena Komarovska-Porokhnyavets Volodymyr Novikov 《Research on Chemical Intermediates》2011,37(8):1009-1027
N′-(4-Oxo-1,4-dihydronaphthalen-1-ylidene)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides and N′-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides were synthesized by reactions
of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone or 2-methyl-1,4-naphthoquinone. The alkylated analogues
of the above products were obtained using ethyl iodide. The interaction of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with
2,3-dichloro-1,4-naphthoquinone was followed by formation of N′-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides. All these compounds were characterized
using 1H, 13C NMR, IR and mass spectra. Some of the new compounds were tested for the antimicrobial and antifungal activity. 相似文献
11.
KlÁra GÁll-IstÓk Lili Sterk GÁbor TÓth Gyula Deák 《Journal of heterocyclic chemistry》1984,21(4):1045-1048
1-(2′-Chloroacetylamino)-4,4-dimethyl-1,4-dihydro-3(2H)-isoquinolinone ( 3 ) was cyclised by treatment with sodium hydride in dimethyl sulphoxide containing 0.1 % of water to give 10,10-dimethyl-6,7,9,10-tetrahydro-5H,14bH-isoquino[2,1-d][1,4]benzodiazepine-6,9-dione ( 4 ) in a yield of 80%. In anhydrous dimethyl sulphoxide the main product of the reaction was 5-N-(4,4-dimethyl-1-phenyl-1,4-dihydro-3(2H)-isoquinolinon-1′-yl)isoquino[2,1-d][1,4]benzodiazepine-6,9-dione ( 5 ), which was also prepared by the reaction of 3 with 4 . 相似文献
12.
The cyclopalladation of two different types of aniline derivatives is described: the acetylated anilines N-(3-methylphenyl)acetamide ( 2a ), 3-(acetylamino)-4-chlorobenzoic acid ( 2c ), and N-(2-chlorophenyl)acetamide ( 2d ) are cyclometalated easily with palladium(II) acetate and trifluoroacetic acid to yield the corresponding complexes 4a, 4c , and 4d , respectively, whereas the acetylated meta-toluidine N-(2-chloro-5-methylphenyl)acetamide ( 2b ) cannot be metalated at the only accessible site between the acetylamino and the methyl group. This aromatic C? H bond can be activated, however, with the second type of meta-toluidine derivatives: the 2-chloro-5, N-dimethyl-N-nitrosoaniline ( 3b ) readily undergoes cyclopalladation to yield the corresponding PdII complex di-μ-trifluoro-acetato-bis[3-chloro-6-methyl-2-(N-methyl-N- nitrosoamino)phenyl-C,N? O]dipalladium(II) ( 5b ) containing a five-membered palladacycle with coordination of PdII at the nitroso N-atom, which is established by 15N-NMR spectroscopy. 相似文献
13.
Several linearly fused tricyclic 6,7,6-systems were prepared. Reaction of 1,2-diamino-4-nitrobenzene with 5,5-dimethylcyclohexan-1,3-dione gave 3-(2-amino-5-nitroaniIino)-5,5-dimethylcyclohex-2-en-1-one (8) . Reaction of 8 and its analogue 6 with various aldehydes gave 2,3,4)5,10,11-hexahydro-3,3-dimethyl-11-substituted-1H-dibenzo[b,e][1,4]diazepin-1-ones 9 and 10 . Acetylation of 9 and 10 gave the corresponding N-acetyl derivatives. Spectral data of the products are discussed. 相似文献
14.
Plectranthons A, B, C, and D. Diterpenoid Phenanthrene-1,4-diones from Leaf-glands a Plectranthus sp. (Labiatae) The following structures of four new 1,4-phenanthraquionones, isolated in minute amounts from the coloured leaf-glands of a Plectranthus sp. obtained from the borders of Lake Kiwu2, Rwanda, are proposed: plectranthon A ( 1 ; 3-hydroxy-5, 7,8-trimethyl-2-(2-propenyl)phenanthrene-1, 4-dione), plectranthon B ( 2 ; 2-(2ξ-acetoxypropyl)-3-hydroxy-5,7,8-trimethylphenanthrene-1,4-dione), plextranthon C ( 3 ; 3-hydroxy- 7,8-diemethyl-2-(2-propenyl)phenanthrene-1,4-dione), and plectranthon D ( 4 ; 3-hydroxy-7,8,10-trimethyl-2-(2-propenyl)phenanthrene-1,4-dione). 2-(2ξ-Hydroxypropyl)-3,6-dihydroxy-5,7,8-trimethylphenanthrene-1,4-dione ( 11 ), a compound very similar to 1–4 , was prepared by a Wagner-Meerwein, rearrangement of coleon E (5). Biogenetically, the plectranthons are derived from abietanoic precursors. The compounds 1, 2 and 4 are the first natural C20-phenanthrenes of diterpenoid origin. 相似文献
15.
Leyla Yurttaş Aslıhan Kubilay Asaf Evrim Evren İpek Kısacık Hülya Karaca Gençer 《Phosphorus, sulfur, and silicon and the related elements》2020,195(9):767-773
AbstractSome new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reacted with hydrazine hydrate (2) then with phenyl isothiocyanate (3). Ring closure by KOH led to 3-mercapto-1,2,4-triazole derivative (4). Lastly, it reacted with 2-chloro-N-(substituted (benzo)/thiazole)acetamide derivatives to obtain the final compounds (5a–j). The structural elucidation of the compounds was performed by 1H NMR and 13C NMR spectroscopy and high resolution mass spectrometry techniques and elemental analysis. The synthesized compounds were investigated for their antimicrobial activities against seven bacteria and four fungi. As a result of the activity studies, it was observed that compounds N-(6-nitrobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5a) and N-(6-fluorobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5d) were the most active molecules. Also, the antifungal activity of the compounds was found to be higher than their antibacterial activity although lower than the standard drug’s potential. Additionally, the physicochemical properties of the compounds were calculated which were evaluated to be at a suitable range for oral administration. 相似文献
16.
Sabutskii Yu. E. Denisenko V. A. Dmitrenok P. S. Polonik S. G. 《Russian Chemical Bulletin》2016,65(3):774-778
A possibility of the synthesis of microbial metabolite Streptomyces catenulae fibrostatin F through the AcOH-catalyzed condensation of 5-hydroxy-3-hydroxymethyl-2,7-dimethoxy1,4-naphthoquinone and its related 3-chloromethyl, 3-acetoxymethyl, and 3-methoxymethyl derivatives with N-acetyl-L-cysteine and paraformaldehyde in 1,4-dioxane was studied. In these conditions, all naphthoquinones gave N-acetyl-S-[(8-hydroxy-3,6-dimethoxy-1,4-dioxonaphthalen-2-yl)methyl]-L-cysteine isomeric to the natural fibrostatin C.
相似文献17.
In the presence of ammonia, methyl N-(bromoacetyl)anthranilate ( 4 ) is cyclized into 3H-1,4-benzodiaze-pine-2,5(1H,4H)-dione ( 1 ). However, when 4 is replaced with methyl N-(chloroacetyl)anthranilate ( 6 ), the only heterocyclic product formed in the reaction is 2-(chloromethyl)quinazoline-4(3H)-one ( 7 ). Under analogous conditions, 3-haloacetamidocrotonates (9, 10) do not yield any heterocyclic products and no 1,4-diazepines can be obtained. 相似文献
18.
T. I. Mukhanova S. Yu. Kukushkin P. Yu. Ivanov L. M. Alekseeva V. G. Granik 《Russian Chemical Bulletin》2007,56(2):325-329
N,N-Dimethylacetamide dimethyl acetal reacted with 5(7)-substituted 2-(hydroxy-methyl)benzofurans to give N,N-dimethyl-2-(2-methylbenzofuran-3-yl)acetamides. Analogous reactions with 3-(hydroxymethyl)indole and 1-hydroxy-6-methyl-1,2,3,4-tetrahydro-carbazole
afforded N,N-dimethyl-3-(3-indolyl)propionamide and N, N-dimethyl-2-(6-methyl-1,2,3,4-tetrahydrocarbazol-1-yl)acetamide, respectively.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 314–318, February, 2007. 相似文献
19.
4,5,7,8-Tetrahydro-6H-imidazo[4,5-e][1,4]diazepine-5,8-dione underwent bromination at the 2-position with or without substituents at the 3-, 4- or 7-position, using bromine, N-bromosuccinimide, or acetyl hypobro-mite. The activation of position 6 with an ester functionality, as in 7 , did not alter the site of bromination. The base-catalyzed bromination of the ring-open precursor, diethyl 2-[N-(1-benzyl-5-nitroimidazolyl-4-carbon-yl)amino]malonate ( 5 ), resulted either in introduction of an alkoxy functionality in the above aminomalonate side-chain, yielding 17 when the reaction was quenched with an alcohol, or in degradation of the side-chain, yielding 1-benzyl-5-nitroimidazole-4-carboxamide ( 19 ) when the reaction was quenched with water. Both 17 and 19 are formed by oxidative bromination of 5 via the bromo intermediate 15 . An indirect evidence for the latter was obtained by base-catalyzed methylation of 5 which gave diethyl 2-methyl-2-[N-(1-benzyl-5-nitroimid-azolyl-4-carbonyl)amino]malonate ( 21 ). The base-catalyzed bromination of 5 with N-bromosuccinimide gave rise to two products, the dimer 24a and the monomer 24b that contained the substituted 2,2-diaminomalon-ate side-chain. The structure of 24b was confirmed by single-crystal X-ray diffraction analyses. Reduction of the 5-nitro group of 17 to the corresponding amino derivative 25 , followed by ring-closure with sodium meth-oxide/methanol, yielded three products, a 5:6-fused system 26 and two 5:7 fused systems 27 and 28 . The structures of 26 and 27 were confirmed by single-crystal X-ray diffraction analyses. A tentative reaction pathway for the formation of all three products has been proposed. Hydrolysis of 27 with aqueous hydrochloric acid resulted in ring-opening to form 5-amino-1-benzylimidazole-4-carboxamide ( 40 ). A mechanism for the hydrolysis reaction has been proposed. Catalytic hydrogenation of 5 in acetic acid yielded the aminoimidazo-lone derivative 11 which upon ring-closure with sodium methoxide in methanol produced imidazo[4,5-e][1,4]-diazepine-2,5,8-trione ( 12 ). 相似文献
20.
《合成通讯》2012,42(1):129-135
AbstractAn expeditious, one-pot multicomponent reaction has been developed for the synthesis of (E)-2-(benzylideneamino)-5-mercapto-4H-1,2,4-triazol-3-yl)-2,3-dihydrophthalazine-1,4-dione derivatives. Condensation of 4-amino-5-hydrazino-4H-1,2,4-triazole-3-thiol with phthalic anhydride and aromatic aldehyde afforded the (E)-2-(benzylideneamino)-5-mercapto-4H-1,2,4-triazol-3-yl)-2,3-dihydrophthalazine-1,4-diones in acetic acid medium with excellent yields. All the synthesized compounds were characterized by their analytical and spectral data. 相似文献