共查询到20条相似文献,搜索用时 46 毫秒
1.
Copper(I)‐Catalyzed Three‐Component Reaction of Terminal Propargyl Alcohols,Aldehydes, and Amines: Synthesis of 3‐Amino‐2‐pyrones and 2,5‐Dihydrofurans
下载免费PDF全文
![点击此处可从《Angewandte Chemie (International ed. in English)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Wu Fan Prof. Dr. Shengming Ma 《Angewandte Chemie (International ed. in English)》2014,53(52):14542-14545
A novel copper(I)‐catalyzed three‐component reaction for the efficient synthesis of 3‐amino‐2‐pyrones and 2,5‐dihydrofurans from propargyl alcohols, aldehydes, and amines has been developed. The starting materials are easily available and the scope of this method is broad. Through mechanistic studies, it is believed that the three‐component reaction consists of an A3‐coupling to propargylic amine, alkyne–allene isomerization, and intramolecular cyclization of the allenol to form a furan. In case of using ethyl glyoxalate as the aldehyde, a ring‐opening, lactonization, and isomerization process affords the 3‐amino‐2‐pyrones. 相似文献
2.
Dervis Gok 《Journal of heterocyclic chemistry》2019,56(12):3343-3353
A simple and easy synthesis of 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carboxylic acid ( 3 ) has been successfully developed through a one‐pot three‐component condensation reaction of (2‐amino‐phenyl)‐oxo‐acetic acid sodium salt ( 1 ) obtained from the hydrolysis of isatin with ammonium acetate and 3‐nitrobenzaldehyde. Some novel quinazoline‐ester derivatives 4‐7 were then obtained by the reaction between the new compound 3 and various alcohols. Then, quinazoline‐amide derivatives 10‐14 were synthesized from the reaction of various amines and 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carbonyl chloride ( 8 ), obtained by the reaction of compound 3 with SOCl2. Finally, some novel quinazoline‐azo derivatives 17‐19 were synthesized by the coupling reaction between β‐dicarbonyl compounds and the novel amino‐quinazoline derivative compound 15 , obtained by reduction of nitro‐quinazoline derivative compound 11 . Thus, a new series of quinazoline‐4‐carboxylic acid, ester, amide, and azo derivatives was synthesized and fully characterized by 1H NMR, 13C NMR, IR, and mass spectrometry analysis. 相似文献
3.
An Approach to the Synthesis of 7‐Amino‐6‐imino‐9‐phenyl‐6H‐benzo[c]chromene‐8‐carbonitrile Derivatives via a Three‐Component Reaction under Ultrasonic Irradiation
下载免费PDF全文
![点击此处可从《Helvetica chimica acta》网站下载免费的PDF全文](/ch/ext_images/free.gif)
An efficient synthesis of 7‐amino‐6‐imino‐9‐phenyl‐6H‐benzo[c]chromene‐8‐carbonitrile derivatives 3 by a three‐component reaction of salicylaldehydes (=2‐hydroxybenzaldehydes) 1 , malononitrile (=propanedinitrile), and 2‐(1‐arylethylidene)malononitrile 2 under ultrasonic irradiation in EtOH is reported. Good yields, short reaction times, and easy purification are the main advantages of the present method. The structures were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2). 相似文献
4.
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
5.
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
6.
Abdolali Alizadeh Hamid Reza Esmaili zand Vahid Saberi Javad Mokhtari 《Helvetica chimica acta》2013,96(12):2240-2244
An efficient approach for the preparation of functionalized 5‐aryl‐3‐(methylsulfanyl)‐1H‐pyrazoles 2 is described. This three‐component reaction between benzaldehydes 1 , NH2NH2?H2O, and 1,1‐bis(methylsulfanyl)‐2‐nitroethene proceeds in EtOH under reflux conditions in good‐to‐excellent yields. The structures of 2 were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS). A plausible mechanism for this type of reaction is proposed (Scheme 2). 相似文献
7.
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
8.
A facile synthesis of trans isomers of 4‐aryl‐3‐methyl‐6‐oxo‐4,5,6,7‐tetrahydro ‐ 2H ‐ pyrazolo[3,4‐b]pyridine‐5‐carbonitriles via three‐component condensation reaction of an aldehyde, 3‐amino‐5‐methylpyrazole and ethyl cyanoacetate in acetonitrile has been developed under microwave irradiation. This one‐pot reaction proceeds without any catalyst in short times and gives the product in high selectivities and high yields. 相似文献
9.
《Journal of heterocyclic chemistry》2017,54(5):2830-2837
A series of novel isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1H‐3‐indolyl)pyrrole‐3‐carboxylates ( 17a – i) were synthesized by a three‐component reaction of 4‐amino‐3‐methyl‐5‐styrylisoxazole 14 , β‐keto ester 15 , and 3‐phenacylideneoxindole 16 , in the presence of CAN catalyst in ethanol. The structures of the synthesized compounds have been established on the basis of spectral and analytical data. The title compounds 17a – i were evaluated for their anti‐inflammatory activity. Compounds 17b and 17c exhibited potent anti‐inflammatory activity as that of standard drug. 相似文献
10.
Zdenka Stiploek Marija indler‐Kulyk KreImir Jakop
i Aleksandar Vinjevac Biserka Koji‐Prodi 《Journal of heterocyclic chemistry》2002,39(1):37-44
Irradiation of styryl‐4‐pyrones 1a‐1d or 2a‐2e (6‐9 × 10?3 M, methanol solution) with filtered (RAYONET photochemical reactor, 300 nm) or unfiltered uv‐light (high‐pressure mercury arc lamp) under aerobic conditions led mainly to dimeric products. Parent 5‐hydroxy‐substituted compounds 1a‐1d yielded exclusively “half‐cage” dimers 3a‐d characteristic for 4‐pyrone dimerization. 5‐Methoxy‐analogues 2a‐2e behave like typical stilbene structures and the mixture of tetrasubstituted cyclobutanes 4 and 5 accompanied with minor amount of phenanthrene‐like compound 6 were the only isolable products of the irradiation. The structure elucidation of products is based on spectral data obtained from MS, IR, 1H NMR and 13C NMR spectra applying COSY, APT, HETCOR, HMBC and NOESY techniques. 相似文献
11.
A series of indeno[2′,1′:5,6]pyrido[2,3‐d]pyrazoles was synthesized by the three‐component reaction of aldehyde, 5‐amino‐3‐methyl‐1‐phenylpyrazole and 1,3‐indenedione in the presence of SDS in aqueous media. The structures were characterized by IR, 1H NMR, high resolution mass spectra and were further confirmed by X‐ray diffraction analysis. 相似文献
12.
A series of novel 2‐aryl‐3‐(9‐alkylcarbazol‐3‐yl)thiazolidin‐4‐ones were synthesized by one‐pot three‐component reactions of 3‐amino‐9‐alkylcarbazoles, aromatic aldehydes, and 2‐mercaptoacetic acid by using dicyclohexylcarbodiimide (DCC) as a cyclizing agent in dry diethyl ether at room temperature. This protocol has advantages of mild condition, short reaction time, high yield, and simple work‐up procedure. 相似文献
13.
Efficient and Expeditious Synthesis of Pyrano‐pyrimidines,Multi‐substituted γ‐Pyrans,and Their Antioxidant Activity
下载免费PDF全文
![点击此处可从《Journal of heterocyclic chemistry》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Khairy A. M. El‐Bayouki Wahid M. Basyouni Tamer K. Khatab Fakhry A. El‐Basyoni Ahmed R. Hamed Eslam A. Mostafa 《Journal of heterocyclic chemistry》2014,51(1):106-115
An efficient, expeditious catalytic route for the synthesis of ethyl 6‐amino‐5‐cyano‐2‐methyl‐4‐aryl‐4H‐pyran‐3‐carboxylates 2 was achieved via a three‐component, one‐pot reaction of malononitrile, ethyl acetoacetate, and various aromatic aldehydes in water as a solvent at room temperature. The key advantages are excellent yield, reaction time, and inexpensive catalyst. Also, cyclization of 4H‐pyrans 2 to the corresponding 4H‐pyrano[2,3‐d]pyrimidines 3 using silica sulfuric acid in the presence of acetic anhydride was described. Some synthesized compounds exhibited promising antioxidant activities. 相似文献
14.
A Convenient One‐Pot Three‐Component Approach for Regioselective Synthesis of Novel Substituted Pyrazolo[1,5‐a]pyrimidines Using Fe+3‐Montmorillonite as Efficient Catalyst
下载免费PDF全文
![点击此处可从《Journal of heterocyclic chemistry》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Roghayeh Hossein nia Manouchehr Mamaghani Farhad Shirini Khalil Tabatabaeian 《Journal of heterocyclic chemistry》2014,51(2):363-367
Novel pyrazolopyrimidines derivatives were synthesized regioselectivly in one‐pot three‐component approach by Fe+3‐montmorillonite catalyzed condensation of 3‐amino‐5‐methyl pyrazole, arylaldehydes, and dimethylmalonate in THF under ultrasonic irradiations and conventional conditions. This rapid method produced the products in short reaction times and good yields. 相似文献
15.
Elmira Ghabraie Morteza Bararjanian Saeed Balalaie Frank Rominger Hamid Reza Bijanzadeh 《Helvetica chimica acta》2011,94(8):1440-1447
The Michael‐type addition of a 4‐hydroxycoumarin (=4‐hydroxy‐2H‐1‐benzopyran‐2‐one) 1 to a β‐nitrostyrene (=(2‐nitroethenyl)benzene) 2 in the presence of AcONH4 leads to substituted (3E)‐3‐[amino(aryl)methylidene]chroman‐2,4‐diones (=(3E)‐3‐[amino(aryl)methylene]‐2H‐1‐benzopyran‐2,4(3H)‐diones) 4 (Table 1). High yields, short reaction time, and easy workup are advantages of this novel one‐pot three‐component reaction. 相似文献
16.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(36):10890-10894
α‐Amino nitriles tethered to alkenes through a urea linkage undergo intramolecular C‐alkenylation on treatment with base by attack of the lithionitrile derivatives on the N′‐alkenyl group. A geometry‐retentive alkene shift affords stereospecifically the E or Z isomer of the 5‐alkenyl‐4‐iminohydantoin products from the corresponding starting E ‐ or Z ‐N ′‐alkenyl urea, each of which may be formed from the same N ‐allyl precursor by stereodivergent alkene isomerization. The reaction, formally a nucleophilic substitution at an sp2 carbon atom, allows the direct regioselective incorporation of mono‐, di‐, tri‐, and tetrasubstituted olefins at the α‐carbon of amino acid derivatives. The initially formed 5‐alkenyl iminohydantoins may be hydrolyzed and oxidatively deprotected to yield hydantoins and unsaturated α‐quaternary amino acids. 相似文献
17.
《Journal of heterocyclic chemistry》2017,54(4):2471-2482
An eco‐friendly method has been developed for the synthesis of 2‐amino‐4‐(9H‐carbazole‐3‐yl)thiophene‐3‐carbonitriles from preliminary carbazole ( 1 ) through an intermediate of 2‐(1‐(9H‐carbazole‐3‐yl)ethylidene)malononitriles using the Knoevenagel condensation followed by the Gewald reaction. On the other hand, the target compounds could also be prepared in a one‐pot three‐component manner by treating equimolar quantities of 1‐(9H‐carbazole‐3‐yl)ethanone ( 3 ), malononitrile, and elemental sulfur. The merits of this preparation are mild reaction conditions. The Gewald reaction is executed with inorganic base NaHCO3 (H2O) in tetrahydrofuran, easy work‐up procedure with good yields. 相似文献
18.
Unexpected One‐pot Synthesis of Novel 2‐Aminopyrimidine‐4‐ones under Microwave Irradiation
下载免费PDF全文
![点击此处可从《中国化学会会志》网站下载免费的PDF全文](/ch/ext_images/free.gif)
One‐pot, three‐component condensation of guanidine, ethylbenzoylacetate and various aromatic aldehydes in the presence of NaHCO3 have been investigated by microwave irradiation. The aromatic aldehydes bearing electron‐withdrawing groups undergo condensation with guanidine and ethylbenzoyl‐acetate to afford ethyl‐2‐amino‐4‐aryl‐1,4‐dihydro‐6‐phenylpyrimidine‐5‐carboxylate derivatives via Biginelli reaction. However, reaction of the aromatic aldehydes having electron‐releasing groups with guanidine and ethylbenzoylacetate did not give the corresponding dihydropyrimidines. Instead, novel 2‐amino‐5‐benzoyl‐5,6‐dihydro‐6‐arylpyrimidine‐4(3H)‐ones were obtained via an unexpected mechanism. 相似文献
19.
Abdolali Alizadeh Zohreh Noaparast Hamideh Sabahno Nasrin Zohreh 《Helvetica chimica acta》2010,93(7):1401-1406
Synthesis and characterization of bis[2‐(arylimino)‐1,3‐thiazolidin‐4‐ones] are described. The one‐pot, pseudo‐five‐component reaction of an aliphatic diamine, isothiocyanatobenzene, and dialkyl but‐2‐ynedioate at room temperature in anhydrous CH2Cl2 gives the title compound in relatively high yield. Under the same conditions, aromatic 1,2‐diamines yield 2‐(arylimino)‐N‐(enaminoaryl)‐1,3‐thiazolidin‐4‐ones in a pseudo‐four‐component reaction. Their structures were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 3). 相似文献
20.
2,4‐Dinitrophenol‐Catalyzed α‐C(sp3)−H and C(sp)−H Bond Functionalization of Cyclic Amines and Alkynes: Highly Regio‐/Diastereoselective Synthesis of α‐Alkynyl‐3‐Amino‐2‐Oxindoles
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Dr. Mukesh Kumar Banni P. Kaur Prof. Swapandeep S Chimni 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(29):9948-9952
A transition‐metal‐ and oxidant‐free DNP (2,4‐dinitrophenol)‐catalyzed atom‐economical regio‐ and diastereoselective synthesis of monofunctionalized α‐alkynyl‐3‐amino‐2‐oxindole derivatives by C?H bond functionalization of cyclic amines and alkynes with indoline‐2,3‐diones has been developed. This cascade event sequentially involves the reductive amination of indoline‐2,3‐dione by imine formation and cross coupling between C(sp3)?H and C(sp)?H of the cyclic amines and alkynes. This reaction offers an efficient and attractive pathway to different types of α‐alkynyl‐3‐amino‐2‐oxindole derivatives in good yields with a wide tolerance of functional groups. The salient feature of this methodology is that it completely suppresses the homocoupling of alkynes. To the best of our knowledge, this is the first example of a DNP‐catalyzed metal‐free direct C(sp3)?H and C(sp)?H bond functionalization providing biologically active α‐alkynyl‐3‐amino‐2‐oxindole scaffolds. 相似文献