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1.
Nonsteroidal Anti‐inflammatory Drug‐based N‐Allylidene Benzohydrazides and 1‐Acyl‐2‐pyrazolines: Their Synthesis as Potential Cytotoxic Agents In Vitro 下载免费PDF全文
Kavitha Kankanala V. Ranga Reddy Yumnam Priyadarshini Devi Lakshmi Narasu Mangamoori D. Rambabu K. Mukkanti Sarbani Pal 《Journal of heterocyclic chemistry》2015,52(1):105-113
A series of 1‐acyl‐2‐pyrazoline derivatives derived from nonsteroidal anti‐inflammatory drugs was designed as potential anticancer agents. Synthesis of these compounds was carried out via the condensation reaction of chalcones and acid hydrazides under heating. The methodology did not require the use of any costly reagents or catalysts, and the acid hydrazide reactants were readily prepared from mefenamic acid or ibuprofen. A variety of 1‐acyl‐2‐pyrazolines was prepared in good to excellent yields. An N‐allylidene benzohydrazide intermediate was isolated during the reaction optimization study, the structure of which was confirmed unambiguously by X‐ray single crystal data. A range of N‐allylidene benzohydrazides were also prepared in good yields. Some of the compounds synthesized showed promising cytotoxic activities when tested against HCT‐15 human colon cancer cell line in vitro. 相似文献
2.
Palladium‐Catalyzed Carbonylative α‐Arylation of 2‐Oxindoles with (Hetero)aryl Bromides: Efficient and Complementary Approach to 3‐Acyl‐2‐oxindoles 下载免费PDF全文
Zhong Lian Stig D. Friis Prof. Dr. Troels Skrydstrup 《Angewandte Chemie (International ed. in English)》2014,53(36):9582-9586
An efficient Pd‐catalyzed carbonylative α‐arylation of 2‐oxindoles with aryl and heteroaryl bromides for the one‐step synthesis of 3‐acyl‐2‐oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the more common oxindole forming reactions. The transformation only requires a mild base and provides good to excellent yields even with heteroaromatic substrates. Employing a near stoichiometric amount of 13COgen, the methodology was easily extended to [13C] acyl labeling. The general applicability of the reaction conditions was demonstrated in the synthesis of a structure related to the pharmaceutically active 3‐acyl‐2‐oxindoles, tenidap. 相似文献
3.
Alpana K. Gupta Mausumi Bharadwaj Ravi Mehrotra 《Journal of heterocyclic chemistry》2019,56(2):703-709
Isatin chalcones and their 3‐hydroxy precursors are shown to possess potential anticancer activity and are also versatile substrates and key intermediates for the synthesis of a large variety of bioactive spiro‐oxindoles. An environmental friendly tandem synthesis, using PEG 400 as green solvent cum phase transfer catalyst, for a series of 3‐hydroxy‐2‐oxindoles and 3‐methylene‐2‐oxindoles has been developed. Reported one‐pot sustainable synthetic strategy was compared with the conventional method and was found to be superior to existing two‐step syntheses in terms of simplicity, product yield, and reaction time and have a large substrate scope. 相似文献
4.
1‐Acetyl‐ and 1‐propionyl‐2‐pyrazolines 11‐27 have been synthesized by the reaction of (3‐coumarinyl)chalcones 1‐10 with hydrazine in hot acetic acid or propionic acid. While 5‐aryl‐3‐(3‐coumarinyl)‐1‐phenyl‐2‐pyrazolines 28‐35 have been prepared by the reaction of (3‐coumarinyl)chalcones 1,3,5‐10 with phenylhydrazine in hot pyridine. Structures of all new compounds have been elucidated by microanalyses, 1H and 13C nmr spectroscopies. 相似文献
5.
Depeng Zhao Dr. Yuan Wang Lijuan Mao Rui Wang Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(41):10983-10987
The first highly enantioselective phosphonylation of α,β‐unsaturated N‐acylpyrroles has been developed. Excellent yields (91–99 %) and enantioselectivities (up to >99 % enantiomeric excess (ee)) were observed for a broad spectrum of both phosphites and N‐acylpyrroles under mild conditions. In particular, when diethyl phosphite was employed to test the scope of the N‐acylpyrroles, almost optically pure products (98 to >99 % ee) were obtained for 20 examples of N‐acylpyrroles. Moreover, optically pure α‐substituted β‐ or γ‐amino phosphonates can be obtained by several simple transformations of the pyrrolyl phosphonates. The versatility of the N‐acylpyrrole moiety makes the phosphorus adducts powerful chiral building blocks that enable the synthesis of various phosphonate‐containing compounds. Finally, the present strategy can also be applied to the asymmetric hydrophosphonylation of N‐acylimines with high enantioselectivities (93 to >99 % ee). 相似文献
6.
《中国化学会会志》2018,65(9):1098-1103
A green and efficient one‐pot two‐step synthesis of ethyl 2‐(alkylimino)‐4‐methyl‐3‐(alkanoyl)‐2,3‐dihydrothiazole‐5‐carboxylates from the reaction between acyl chlorides, ammonium thiocyanate, primary alkylamines, and ethyl 2‐chloroacetoacetae under mild, solvent‐ and catalyst‐free conditions at room temperature is presented. This efficient and straightforward technique gave the expected products in good to high yields in 2–4 hr without the creation of any by‐product in all reactions. 相似文献
7.
Roberta Settambolo 《Journal of heterocyclic chemistry》2015,52(3):896-901
A pathway for the formation of 3‐butadienyl‐1‐tosylpyrroles from 3‐acyl derivatives via secondary and tertiary 3‐hydroxyalkyl‐1‐tosylpyrroles has been developed. The dehydration of the alcohols intermediates is the crucial step: conditions for high chemo‐ and diastereocontrol are described. 相似文献
8.
Kenji Yamagata Fumi Okabe Hiroshi Maruoka Yoshinobu Tagawa 《Journal of heterocyclic chemistry》2005,42(4):543-549
The reaction of 2‐acylamino‐4,5‐dihydro‐3‐furancarbonitriles 1 with sodium iodide in N,N‐dimethyl‐formamide gave the corresponding 1‐acyl‐2‐oxo‐3‐pyrrolidinecarbonitriles 2 in good yields. Successive treatment of 1 with titanium(IV) chloride and potassium carbonate resulted in the formation of N‐acyl‐1‐cyanocyclopropanecarboxamides 4 . The same compounds 2 were also obtained by treatment of 4 with sodium iodide. The starting compounds 1 were synthesized by the reaction of 2‐amino‐4,5‐dihydro‐3‐furan‐carbonitrile with acyl chlorides in pyridine. 相似文献
9.
Synthesis of 1‐Acyl‐3,4‐dihydroquinazoline‐2(1H)‐thiones by Cyclization of N‐[2‐(Isothiocyanatomethyl)phenyl] Amides Generated in situ from N‐[2‐(Azidomethyl)phenyl] Amides 下载免费PDF全文
An efficient method for the preparation of 1‐acyl‐3,4‐dihydroquinazoline‐2(1H)‐thiones 5 has been developed. The reaction of N‐[2‐(azidomethyl)phenyl] amides 3 , easily prepared by a three‐step sequence starting with (2‐aminophenyl)methanols, with Ph3P, followed by CS2, allowed generation of N‐[2‐(isothiocyanatomethyl)phenyl]‐amide intermediates 4 , which underwent cyclization on treatment with NaH to furnish the corresponding desired products in generally good yields. 相似文献
10.
Old Selenium Heterocycles Revisited: Synthesis,Spectroscopic, and Structural Characterization of N‐Acyl‐1,3‐selenazol‐2(3H)‐imines and 5‐Acyl‐1,3‐selenazol‐2‐amines from Acylselenourea Derivatives 下载免费PDF全文
Fabian Mohr 《Journal of heterocyclic chemistry》2014,51(5):1435-1441
A series of five‐membered selenium heterocycles was prepared from the reaction of various selenoureas and phenacyl bromides. In the case of 1‐acyl‐3‐arylselenoureas N‐acyl‐1,3‐selenazol‐2(3H)‐imines are formed, whereas the analogous reaction with 3,3‐disubstituted 1‐acylselenoureas affords 5‐acyl‐1,3‐selenazol‐2‐amines. The compounds were characterized by NMR spectroscopy and mass spectrometry. In addition, the proposed structures were unambiguously confirmed by X‐ray diffraction studies. 相似文献
11.
A Facile Synthesis of Some New 1‐Benzothiazolyl‐3‐aryl/Hetaryl‐5‐(3‐aryl‐1‐phenyl‐4‐pyrazolyl) Pyrazoles and Their Antimicrobial Activity 下载免费PDF全文
Sushma Singh Vijaykiran Punia Chetan Sharma K. R. Aneja Om Prakash Rashmi Pundeer 《Journal of heterocyclic chemistry》2015,52(6):1817-1822
Some new derivatives of 1‐benzothiazolyl‐3‐aryl/hetaryl‐5‐(3‐aryl‐1‐phenyl‐4‐pyrazolyl) pyrazoles were synthesized by the cyclocondensation of 1‐aryl/hetaryl‐3‐(3‐aryl‐1‐phenyl‐1H‐pyrazole‐4‐yl)prop‐2‐en‐1‐ones (pyrazolyl chalcones) and 6‐substituted‐2‐hydrazinobenzothiazoles. 相似文献
12.
《中国化学》2018,36(1):20-24
A highly regio‐, diastereo‐ and enantioselective addition of 2‐acyl imidazoles or 2‐acyl pyridines with allenes promoted by Rh/Lewis acid synergistically catalytic system is described. This atom economic approach leads to the formation of the branched allylic alkylated products including acyclic quaternary all‐carbon stereogenic centres in good yields with good to excellent diastereo‐ and enantioselectivities. Kinetic studies reveal that the rate‐determining step in this process is the oxidative addition of Rh(I) with C—H bond. 相似文献
13.
Alexey Kirilin Serap Sahin Päivi Mäki‐Arvela Johan Wärnå Tapio Salmi Dmitry Yu. Murzin 《国际化学动力学杂志》2010,42(10):629-639
The kinetics of the acylation of (R,S)‐1‐phenylethanol was investigated using lipase as a catalyst. The main parameters were temperature, reaction atmosphere, different acyl donors, and different amounts of acyl donor as well as the presence of some additives in the reaction mixture. The initial reaction rate increased with increasing temperature and with a decreasing amount of an acyl donor. The activated esters, such as isopropenyl‐ and vinyl acetate, exhibited very high acylation rates for R‐1‐phenylethanol, whereas low rates were obtained with ethyl acetate and 2‐methoxyethyl acetate. The addition of water and acetophenone decreased the acylation rate. A kinetic model was developed based on a sequential step mechanism, in which enzyme was reacting in the first step with an acyl donor followed by the reaction of a modified enzyme complex with the reactant, R‐1‐phenylethanol. Comparison with experimental data obtained at different temperatures allowed simplification of this model, leading to a kinetic equation with just one apparent parameter. The influence of the amount of acyl donor, ethyl acetate, could be quantitatively described by taking into account the competitive inhibition of the ethanol produced. The rate constants and apparent activation energy for experiments performed under different temperatures and the amounts of acylation agent were determined. The apparent activation energy was 24.5 kJ/mol. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 629–639, 2010 相似文献
14.
In the present investigation, the first incorporation of both ferrocene scaffold and 1,2‐dihydro‐2‐oxopyridine‐3‐carbonitrile pharmacophore leading to a series of structurally novel ferrocene‐based hybrids has been achieved, involving the condensation reaction of ferrocenyl substituted chalcones with 2‐cyanoacetamide in a freshly prepared EtONa solution at 70°. The molecular structures of these newly synthesized products were confirmed by IR, and 1H‐ and 13C‐NMR analyses. 相似文献
15.
Silvia E. Asías Ana M. Bruno Diego A. Dominici Mariela Bollini Carlos H. Gaozza 《Journal of heterocyclic chemistry》2003,40(1):107-112
In order to find new antimalarial drugs, an exploration about the chemical properties of the starting compounds 3‐amino‐6‐chloro‐4‐phenyl‐1H‐quinolin‐2‐one ( 1 ) and 3‐amino‐4‐methyl‐1H‐quinolin‐2‐one ( 2 ) was developed. Acylation with acyl chloride, sulfonyl chloride and acetic anhydride were carried out. Despite a previous report [2], when acetyl chloride or acetic anhydride were assayed on 1 , only the diacetyl derivative 7 was obtained. When this compound was heated at reflux temperature in a mixture of acetic acid and acetic anhydride, it was transformed in the oxazoloquinoline 8 . Further reactions of the acyl derivatives with diazomethane afforded 1‐methylated compounds. Compound 2 gave the imine 16 by condensation with 4‐nitrobenzaldehyde. 相似文献
16.
Visible‐Light‐Promoted Iminyl‐Radical Formation from Acyl Oximes: A Unified Approach to Pyridines,Quinolines, and Phenanthridines 下载免费PDF全文
Heng Jiang Xiaode An Kun Tong Tianyi Zheng Prof. Dr. Yan Zhang Prof. Dr. Shouyun Yu 《Angewandte Chemie (International ed. in English)》2015,54(13):4055-4059
A unified strategy involving visible‐light‐induced iminyl‐radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac‐[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e? reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N‐containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible‐light‐induced iminyl‐radical formation was successfully applied to a five‐step concise synthesis of benzo[c]phenanthridine alkaloids. 相似文献
17.
Tetsuo Ohta Hironori Fujisawa Mitsuru Kawazome Yasuto Nakai Isao Furukawa 《Journal of heterocyclic chemistry》2001,38(1):159-164
Novel method for the synthesis of 3‐acyl‐1,6‐dialkyl‐7‐methyl‐1,6‐naphthyridine‐2,5(1H,6H)‐diones (2) was developed. The reaction of 2‐acyl‐1‐alkylamino‐1‐ethoxyethylenes (1) with acetyl chloride or β‐keto amide 3 with acetyl chloride in the presence of p‐toluenesulfonic acid gave 2 in moderate yield (14‐59% yield). 相似文献
18.
Heng Jiang Xiaode An Kun Tong Tianyi Zheng Yan Zhang Shouyun Yu 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2015,127(13):4127-4131
A unified strategy involving visible‐light‐induced iminyl‐radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac‐[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e− reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N‐containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible‐light‐induced iminyl‐radical formation was successfully applied to a five‐step concise synthesis of benzo[c]phenanthridine alkaloids. 相似文献
19.
A novel oridonin derivative substituted with 3‐((2,3‐dihydroxypropyl)dithio)‐propionyl group at 14‐O position was synthesized through a two‐step procedure: Esterification of oridonin with 3‐(2‐pyridyldithio)propanoic acid and the subsequent thiol‐disul?de exchange reaction with 3‐mercapto‐1,2‐propanediol. The bioreduction‐responsive disulfide bond in the compound leads to high leaving ability of the 14‐O acyl moiety when treated with glutathione as monitored by reverse phase high‐performance liquid chromatography. 相似文献
20.
We hereby report the first preparation of the 5,6‐dihydro‐4H‐furo[2,3‐c]pyrrol‐4‐one ( 3 ) and its derivatives starting from methyl 3‐(methoxycarbonyl)furan‐2‐acetate ( 8 ). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9 . Conversion of 9 into the acyl azide 10 followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Scheme 3). Intramolecular cyclization reactions provided the target compounds (Scheme 5). Removal of the amine‐protecting group formed the title compound 3 . 相似文献