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1.
N‐tert‐Butyl‐N‐benzoylhydrazine was prepared in a new and convenient procedure with good yield. Triphosgene underwent reaction with three equivalents of N‐t‐butyl‐N‐benzoylhydrazine using six equivalents of triethylamine as a base to yield the cyclic tetramer of N‐t‐butyl‐N‐isocyanatobenzoylamide. Treatment of triphosgene with three equivalents of N‐t‐butyl‐N‐benzoylhydrazine either in the presence of three equivalents of triethylamine or in the absence of triethylamine afforded the cyclic pentamer of iso‐cyanate, from which tert‐butyl is eliminated. 相似文献
2.
Synthesis of 1‐Arylethyl‐2‐arylethylamino‐5‐trifluoroacetyl‐1,2,3,4‐tetrahydropyridines and Related Compounds with Potential Cell Efflux Pump Inhibition
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Nilo Zanatta Marcio M. Lobo Josiane M. dos Santos Laura de A. Souza Valquiria P. de Andrade Helio G. Bonacorso Marcos A. P. Martins 《Journal of heterocyclic chemistry》2015,52(6):1776-1781
This study reports a simple, fast, and efficient method for the synthesis of a new series of 1‐arylethyl‐2‐arylethylamino‐5‐trifluoroacetyl‐1,2,3,4‐tetrahydropyridines and related compounds from the reaction of 2‐alkoxy‐5‐trifluoroacetyl‐3,4‐dihydro‐2H‐pyrans with 2‐arylethanamines and related 2‐ethanamines. The desired tetrahydropyridines were obtained in excellent yields (90–98%), through a reaction that can be described as an AAB′ three‐component reaction protocol following an ANRORC‐type mechanism. 相似文献
3.
Masilamani Jeganmohan Dr. Sivakolundu Bhuvaneswari Dr. Chien‐Hong Cheng Prof. Dr. 《化学:亚洲杂志》2010,5(1):153-159
The reaction of benzynes with N‐heteroaromatics including quinolines, isoquinolines, and pyridines and various terminal alkynes or ketones with an α‐hydrogen in the presence of KF and 18‐crown‐6 in THF at room temperature for 8 h gave various N‐arylated 1,2‐dihydroheteroaromatics in good to moderate yields. Some of these product structures are found in various naturally occurring and biologically active heterocyclic compounds. The reaction involves an unusual multiple construction of new C? C, C? N, and C? H bonds and the cleavage of a C? H bond in one pot. It is likely that the three‐component coupling proceeds through the nucleophilic addition of quinoline to benzyne, which generates a zwitterionic species. The latter then attracts a proton from terminal alkyne (or ketone) to generate an N‐arylated quinolinium cation and an acetylide anion. Further reaction of these two ions provides the final substituted 1,2‐dihydroquinolines. In the reaction, the terminal alkyne acts first as a proton donor and then as a nucleophile. The application of a three‐component coupling reaction product, 1,2‐dihydro‐2‐pyridinyl alkyne in a stereospecific [4+2] Diels–Alder cycloaddition reaction with N‐phenyl maleimide to give an isoquinuclidine derivative, an important core present in various natural products, is demonstrated. 相似文献
4.
Kavitha Kotthireddy Srikrishna Devulapally Pramod Kumar Dubey Aparna Pasula 《Journal of heterocyclic chemistry》2019,56(3):938-946
A facile, convenient, and adequate method has been developed for the synthesis of novel 5‐amino‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐7‐aryl‐7H‐thiazolo[3,2‐a]pyridine‐6,8‐dicarbonitriles ( 6 ) by employing 2‐(4‐(2‐oxo‐2H‐chromen‐3‐yl)thiazol‐2‐yl)acetonitrile ( 3 ) as an important precursor. Initially, we have synthesized the target compounds in a stepwise manner and then approached a tandem method to examine the feasibility of one‐pot method. Subsequently, one‐pot three‐component protocol has been established for the synthesis of title compounds by the reaction of 3 with benzaldehyde and malononitrile in refluxing ethanol engender a new six‐membered thiazolo[3,2‐a] pyridine as a hybrid scaffold. Reaction conditions were optimized for this reaction and a broad substrate scope with various aryl and heteroaryl aldehydes make this protocol very practical, attractive, and worthy. Mechanistic aspects for the formation of these compounds were outlined comprehensively. Characterization of these newly synthesized compounds was achieved by means of IR, 1H NMR, 13C NMR, and HRMS. 相似文献
5.
Ahmad Poursattar Marjani Jabbar Khalafy Ayda Farajollahi 《Journal of heterocyclic chemistry》2019,56(1):268-274
In this research, in order to synthesize a series of ethyl 2‐amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline‐3‐carboxylates, a green and an efficient method is proposed through one‐pot three‐component reaction of substituted arylglyoxals, ethyl cyanoacetate, and 4‐hydroxyquinolin‐2(1H)‐one in the presence of terapropylammonium bromide as a catalyst in good yields. All synthesized new substances were characterized by FTIR, 1H‐NMR, and 13C‐NMR spectral data and elemental analysis. 相似文献
6.
Anka Pejović Dragana Stevanović Ivan Damljanović Mirjana Vukićević Sladjana B. Novaković Goran A. Bogdanović Tatjana Mihajilov‐Krstev Niko Radulović Rastko D. Vukićević 《Helvetica chimica acta》2012,95(8):1425-1441
A successful aza‐Michael addition of arylamines to a conjugated enone, acryloylferrocene, has been achieved by ultrasonic irradiation of the mixture of these reactants and the catalyst, i.e., montmorillonite K‐10. This solvent‐free reaction, yielding ferrocene containing Mannich bases, 3‐(arylamino)‐1‐ferrocenylpropan‐1‐ones, considered as valuable precursors in organic synthesis, has been performed by using a simple ultrasonic cleaner. Among 17 synthesized β‐amino ketones, three were new ones, and these were fully characterized by spectroscopic means. X‐Ray crystallographic analysis of three of these crystalline products enabled the insight into the conformational details of these compounds. All compounds were evaluated for their antibacterial activities against six Gram‐positive and five Gram‐negative strains in a microdilution assay. The observed promising antibacterial activity (with a MIC value of 25 μg/ml (ca. 0.07 μmol/ml) as the best result for almost all tested compounds against Micrococcus flavus) seems not only to be compound but also bacterial species‐specific. 相似文献
7.
Facile Assembly of Benzo[b]naphtho[2,3‐d]azocin‐6(5 H)‐ones by a Palladium‐Catalyzed Double Carbometalation
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The palladium‐catalyzed reaction of 2‐alkynylanilines with 2‐(2‐bromobenzylidene)cyclobutanone as an efficient route to 7,8‐dihydrobenzo[b]naphtho[2,3‐d]azocin‐6(5 H)‐ones was developed. The fused eight‐membered ring was constructed conveniently. During the reaction process, double carbometalation was involved, which resulted in excellent selectivity with the formation of three new bonds. This transformation is highly efficient and leads to fused polycycles in good to excellent yields with good functional group tolerance. 相似文献
8.
Visible‐Light‐Induced Trifluoromethylation of Isonitrile‐Substituted Methylenecyclopropanes: Facile Access to 6‐(Trifluoromethyl)‐7,8‐Dihydrobenzo[k]phenanthridine Derivatives
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Yu‐Chao Yuan Hou‐Lu Liu Xu‐Bo Hu Prof. Dr. Yin Wei Prof. Dr. Min Shi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(37):13059-13063
A new visible‐light‐induced trifluoromethylation of isonitrile‐substituted methylenecyclopropanes is developed. A range of substituted 6‐(trifluoromethyl)‐7,8‐dihydrobenzo[k]phenanthridine derivatives are readily furnished by this newly developed tandem reaction with moderate to good yields. This reaction allows the direct formation of two six‐membered rings and three new C?C bonds, including the C?CF3 bond, under visible light irradiation. 相似文献
9.
M. P. Stoyanova I. D. Kozekov M. D. Palamareva 《Journal of heterocyclic chemistry》2003,40(5):795-803
Stereochemical course of the reaction of homophthalic anhydride and N‐(1‐methyl‐1H‐pyrrol‐2‐yl‐methylidene)‐phenethylamine was studied. Mixtures of the expected trans‐ and cis‐1,2,3,4‐tetrahydroiso‐quinoline‐4‐carboxylic acids trans‐ 4 and cis‐ 4 were obtained along with by‐products 5 and 6 . The ratios of all products and the diastereomers, obtained under different reaction conditions, were established by pmr. THF as a solvent and ultrasonic treatment are applied for the first time in the reaction of this type. The reaction was made diastereoselective towards any isomer. The carboxylic group of trans‐ 4 was transformed in four steps into various cyclic amino‐methyl groups yielding numerous new tetrahydroisoquinolinones trans‐ 10a‐i incorporating a given fragment of pharmacological interest. Reduction of 10a‐i was studied. 相似文献
10.
Zhengfeng Xie Fangming Liu Yonghai Hui Caihong Liu Yadong Sun 《Journal of heterocyclic chemistry》2005,42(4):695-697
A series of new 3‐(4‐oxo‐4H‐chromen‐3‐yl)‐3a,6a‐dihydropyrrolo[3,4‐d]isoxazole‐4,6‐dione have been synthesized by the reaction of N‐arylmaleimides with nitrile oxide, prepared from α‐chloro‐4‐oxo‐4H‐chromen‐carbaldehyde oximes in situ through 1,3‐dipolar cycloaddition reaction. The structures of all new compounds were confirmed by elemental analysis, ir,1H nmr and mass spectral data. 相似文献
11.
Amrah Nouri Ahmad Poursattar Marjani Jabbar Khalafy 《Journal of heterocyclic chemistry》2019,56(10):2912-2921
A new series of benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium hydroxide derivatives have been synthesized by the one‐pot, three‐component reaction of aryl glyoxal monohydrates, 2‐hydroxy‐1,4‐naphthoquinone, and 2‐aminothiazole or 2‐aminobenzothiazole in the presence of triethylamine and p‐toluenesulfonic acid as organocatalysts in H2O/acetone (2:1) at room temperature. This method offers mild reaction conditions, excellent yields, easy workup, and readily accessible starting materials and catalysts. 相似文献
12.
Mohammad Bakherad Ali Keivanloo Zohreh Bakherad Zahra Toozandejani Mohamad Mahdavi 《中国化学会会志》2019,66(6):674-682
Magnetized water (MW) is used as a green and new solvent‐promoting medium for the one‐pot, three‐component synthesis of novel 1,2,3‐triazole‐linked indoles catalyzed by copper iodide. A broad range of 2‐aryl‐1‐(prop‐2‐ynyl)‐1H‐indole‐3‐carbaldehydes were reacted with alkyl halides and sodium azide via copper‐catalyzed azide–alkyne cycloaddition reactions in MW in the absence of any ligand. This method offers the advantages of short reaction times, green procedure, low cost, simple work‐up, quantitative reaction yields, and no need for any organic solvent. 相似文献
13.
Amine‐Promoted One‐Pot,Multicomponent Route to Spiro‐Fused‐Pyran Derivatives in Aqueous Media
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The primary amine‐promoted synthesis of spiro‐fused‐pyran derivatives via the three‐component reaction of ninhydrin, malononitrile, and cyclic 1,3‐diketo compounds is described. This new methodology affords the title compounds in high yields and short time, and with easy workup without chromatographic purification steps or extraction. All structures were confirmed by IR, 1H‐ and 13C‐NMR spectroscopy, and mass spectroscopy. A plausible mechanism for this type of reaction is proposed (Scheme 2). 相似文献
14.
Biswanath Das D. Nandan Kumar Keetha Laxminarayana B. Ravikanth 《Helvetica chimica acta》2007,90(7):1330-1334
The synthesis of 14‐aryl‐ or 14‐alkyl‐14H‐dibenzo[a,j]xanthenes 3 involving the treatment of naphthalen‐2‐ol ( 1 ) with arenecarboxaldehydes or alkanals 2 in the presence of HClO4?SiO2 as a heterogeneous catalyst was achieved (Table 1), and this reaction was extended to the preparation of N‐[(2‐hydroxynaphthalen‐1‐yl)methyl]amides 5 by a three‐component reaction with urea ( 4a ) or an amide 4b – d as a third reactant (Table 2). 相似文献
15.
Nabila Aït‐Baziz Yahia Rachedi Maamer Hamdi Artur M. S. Silva F. Balegroune Roisnel Thierry N. Sellier 《Journal of heterocyclic chemistry》2004,41(4):587-591
The synthesis and reactivity studies of 4‐hydroxy‐6‐methyl‐3‐(5‐phenyl‐2E,4E‐pentadien‐1‐oyl)‐2H‐pyran‐2‐one 2 with nucleophiles are reported. Reactions of 2 with hydrazine derivatives gave new pyrazole‐type com pounds while the reaction with ortho‐phenylenediamines yielded 1,5‐benzodiazepines. The reaction of 2 with ethylamine implies the 2H‐pyran‐2‐one ring opening and the formation of a strong conjugated compound 3. 相似文献
16.
《Journal of heterocyclic chemistry》2017,54(5):2822-2829
For a wide spectrum of pharmacological effects of polyhydroquinolines, this study introduces a developed safe, simple, higher yields and fast method for the synthesis of some new hexahydroquinoline derivatives using one‐pot three‐component cyclocondensation reaction, via the reaction of 1,3‐cyclohexanedione with primary amine and arylidinemalononitrile or salicylaldehyde derivatives. The prepared compounds were reacted with different reagents as N ,N‐dimethylformamide dimethylacetal, acetic anhydride, sulphuric acid, and hydrazine hydrate forming several polycyclic hexahydroquinoline and acridine derivatives. All these new compounds have been characterized by spectral data and expected to be effective pharmaceutical drugs. 相似文献
17.
Piperazine‐functionalized nickel ferrite (NiFe2O4) nanoparticles were synthesized as recoverable heterogeneous base catalysts using a routine method. The synthesized materials were characterized using various spectroscopic techniques such as infrared, X‐ray diffraction, scanning electron microscopy, energy‐dispersive X‐ray, thermogravimetry analysis, and vibrating sample magnetometry. Catalytic efficiency was investigated in the synthesis of 2‐amino‐4H‐chromene derivatives via a one‐pot three component reaction of aldehyde and malononitrile with β or α‐naphthol/5‐methyle resorcinol under solvent‐free conditions with good to high yields. This method is operationally simple and has several advantages such as good to high yield, short reaction times, solvent‐free conditions, and easy synthesis. Moreover, the catalyst was recovered easily using an external magnet and reused three times without distinctive loss in catalytic activity. 相似文献
18.
Cristina Ferris M. Violante de Paz Juan A. Galbis 《Journal of polymer science. Part A, Polymer chemistry》2011,49(5):1147-1154
Three new polymerizable diols, based on mono‐, di‐, and tri‐O‐allyl‐L ‐arabinitol derivatives, were prepared from L ‐arabinitol as versatile materials for the preparation of tailor‐made polyurethanes with varied degrees of functionalization. Their allyl functional groups can take part in thiol‐ene reactions, to obtain greatly diverse materials. This “click” reaction with 2‐mercaptoethanol was firstly studied on the highly hindered sugar precursor 2,3,4‐tri‐O‐allyl‐1,5‐di‐O‐trityl‐L ‐arabinitol, to apply it later to macromolecules. A polyurethane with multiple pendant allyl groups was synthesized by polyaddition reaction of 2,3,4‐tri‐O‐allyl‐L ‐arabinitol with 1,6‐hexamethylene diisocyanate, and then functionalized by thiol‐ene reaction. The coupling reaction took place in every allyl group, as confirmed by standard techniques. The thermal stability of the novel polyurethanes was investigated by thermogravimetric analysis and differential scanning calorimetry (DSC). This strategy provides a simple and versatile platform for the design of new materials whose functionality can be easily modified. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献
19.
The hitherto unreported, highly functionalized 1H‐pyrazole‐3‐carboxylates 3 have been synthesized in good yields via a one‐pot three‐component domino reaction of phenylhydrazines, dialkyl acetylenedicarboxylates, and ninhydrin under mild conditions for the first time. No co‐catalyst or activator is required for this multicomponent reaction, and the reaction is, from an experimental point of view, simple to perform (Scheme 1). The structures of compounds 3 were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization/addition reaction is proposed (Scheme 2). 相似文献
20.
The reaction of homophthalic anhydride and N‐(1‐methyl‐1H‐pyrrol‐2‐yl‐methylidene)‐benzylamine in boiling benzene afforded as a main product the expected substituted trans‐1,2,3,4‐tetrahydroisoquinoline‐4‐carboxylic acid 5 . The carboxylic group of 5 was transformed in four steps into cyclic amino‐methyl groups yielding numerous new tetrahydroisoquinolinones 11a‐j incorporating a given fragment of pharmacological interest. Reduction of 11a‐j was studied. 相似文献