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1.
Oxidation of 2-aryl-2,3-dihydro-4(1H)-quinolones (1) with 1.5 equivalents of (dichloroiodo)benzene in dichloromethane at room temperature leads to regioselective chlorination, thereby offering an efficient method for the synthesis of new 2-aryl-6-chloro-2,3-dihydro-4(1H)-quinolones (3). 相似文献
2.
《Journal of Coordination Chemistry》2012,65(10):1785-1794
Ligands derived from quinoxaline-2,3-(1,4H)-dithione are treated with Co(II), Ni(II), Cu(II), and Zn(II) chlorides to yield stable complexes. The prepared compounds are characterized by spectro-analytical techniques and magnetic susceptibility measurements, and the coordination behavior of ligands is discussed. All the complexes are octahedral and mononuclear with general formula [MLCl2(H2O)]. The electrochemical behavior of the synthesized compounds was investigated by cyclic voltammetry studies and the redox activity is explained. 相似文献
3.
A new and convenient method for the preparation of 2‐aryl‐2,3‐dihydro‐1,8‐naphthyridin‐4(1H)‐ones 4 has been developed. Thus, N‐{3‐[(2E)‐3‐arylprop‐2‐enoyl]pyridin‐2‐yl}‐2,2‐dimethylpropanamides 3 are synthesized from commercially available pyridin‐2‐amine using an easily performed three‐step sequence and are subjected to cyclization with deprotection under acidic conditions in H2O to give the desired products. Similarly, 2‐aryl‐2,3‐dihydro‐1,7‐naphthyridin‐4(1H)‐ones 8 and 2‐aryl‐2,3‐dihydro‐1,6‐naphthyridin‐4(1H)‐ones 12 can be prepared from pyridin‐3‐amine and pyridin‐4‐amine, respectively. 相似文献
4.
Dr. Jun Ying Jian-Shu Wang Lingyun Yao Dr. Wangyang Lu Prof. Dr. Xiao-Feng Wu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(64):14565-14569
A new procedure on palladium-catalyzed carbonylative cyclization of N-(2-pyridyl)sulfonyl (N-SO2Py)-2-iodoanilines with terminal alkenes has been developed for the rapid construction of dihydroquinolin-4(1H)-one scaffolds. Enabled by the chelating group and using benzene-1,3,5-triyl triformate (TFBen) as the CO source, both aromatic and aliphatic alkenes were smoothly transformed into the corresponding 2,3-dihydroquinolin-4(1H)-ones in good yields with excellent regioselectivities. Notably, the reaction of aromatic alkenes produces 2-aryl-2,3-dihydroquinolin-4(1H)-ones, while 3-alkyl-2,3-dihydroquinolin-4(1H)-ones were obtained when aliphatic alkenes were used. This protocol has been applied in the synthesis of antitumor agent A as well. 相似文献
5.
Gustav Zigeuner Klaus Schweiger Dietmar Habernig 《Monatshefte für Chemie / Chemical Monthly》1982,113(5):573-581
4-Alkylamino-2(1H)-pyridinethiones (1) react with bis-trichlorphenylethylmalonate (3) to give four isomeric products: 5-thioxo-1,6-naphthyridine-2(1H)-ones (4), 7,7-dimethyl-4H-thiopyrano[2,3-b]pyridine-4-ones (6), 2,2-dimethyl-2H-thiopyrano[2,3-b]pyridine-5,7-dioles (7) and 2,2-dimethyl-2H-thiopyrano[2,3-b]pyridine-5(3H)-ones (8). On treatment with alkali the thioxogroup of4 is hydrolyzed and 1,6-naphthyridinediones (5) are formed. Compound5 can also be synthesized by heating the alkylaminopyridones (2) together with3.6 can be hydrolyzed to 2-thioxo-3-pyridylpropylketones (12). On treatment with diluted alkali or conc. acid the aminogroup of7 and8 is hydrolyzed and10 is formed. By heating in 20% NaOH10 is transformed to the dihydroxymercapto-3-pyridylmethylketone (11).
Herrn Prof. Dr.Erich Ziegler mit den besten Wünschen zum 70. Geburtstag gewidmet. 相似文献
6.
N. E.H. Mustaphi S. Ferfra E. M. Essassi B. Garrigues M. Pierrot 《Phosphorus, sulfur, and silicon and the related elements》2013,188(11):2265-2271
La condensation de la quinoxaline-2,3-dithione 1avec le benzoylhydrazide 2dans le DMF conduit à la 1-phényl-4-diméthylamino-1,2,4-triazolo [4,3-a] quinoxaline 5, à coté de la 3-diméthylaminoquinoxaline-2-thione 3et de la diméthylaminoquinoxalin-2-one 4. 相似文献
7.
Isothiocyanate 2, obtained from aza-Wittig reaction of iminophosphorane 1 with CS2, reacted with amine to give 2-thioxo-2,3,5,6,7,8-hexahydrobenzothieno[2,3-d]pyrimidin-4(1H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones 5 in good yields. 相似文献
8.
A mild, efficient, and high-yielding method for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones from their corresponding 2-amino chalcones using silica chloride (SiO2Cl) under solvent-free conditions is described. A series of 2-aryl-2,3-dihydroquinolin-4(1H)-ones containing both electron-donating and electron-withdrawing substituents were synthesized. 相似文献
9.
A series of 3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 6-iodo-3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones were synthesized in choline chloride/urea deep eutectic solvent. Substituted 2-mercapto-4(3H)-quinazolinones were synthesized from anthranilic acid or 5-iodoanthranilic acid and appropriate isothiocyanates in good to excellent yields. Isolation of final product was easy and required no further purification. Synthesis of these compounds was rapid, selective, and catalyst free, while preparation of deep eutectic solvent was easy, components are readily available, cheap, and environmentally friendly. 相似文献
10.
Krishna Sai Gajula Naresh Mameda Srujana Kodumuri Durgaiah Chevella Rammurthy Banothu Vasu Amrutham 《合成通讯》2013,43(22):2866-2876
The synthesis of 2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation of anthranilamide with ketones in aqueous media using Hβ zeolite is reported. The scope of the reaction was explored by various ketones such as aromatic, aliphatic and cyclic ketones. Based on the preliminary mechanistic results, a tentative mechanism for the formation of 2,3-dihydroquinazolin-4(1H)-ones using zeolite catalyst (Hβ) is predicted. The reusability study, large-scale experiment and water as solvent showed significant benefits of this catalytic protocol in comparing to earlier methods. 相似文献
11.
4‐Halo‐2(5H)‐furanones were prepared by the halolactonization of 2,3‐allenoic acids. The subsequent Suzuki coupling reaction of 4‐halo 2(5H)‐furanones with aryl boronic acids was carried out to produce 4‐aryl‐2(5H)‐furanones in excellent yields. 相似文献
12.
Zhansheng Wang Mengyao Wang Shuangshuang Xu Mengmeng Gu Zhiying Meng Chuan Li 《合成通讯》2016,46(23):1887-1892
An efficient and facile method for the synthesis of 5-arylindeno[2′,1′:5,6]pyrido[2,3-d] pyrimidine-2,4(3H)-dione and 7-arylbenzo[h]pyrimido[4,5-b]quinoline-8,10(5H,9H)-dione derivatives from the reactions of 2-arylidene-2,3-dihydroinden-1-one (or 2-arylidene-3,4- dihydronaphthalen-1(2H)-one) and 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione under mild conditions was described. This is a simple, efficient, and very rapid synthetic method, which is believed to provide a useful process for the synthesis of these fused heterocyclic compounds. The products were confirmed by infrared, 1H NMR, 13C NMR, and high-resolution mass spectrometry. 相似文献
13.
Chidrawar Ajay Devulapally Yogananda Chary Dr. Sridhar Balasubramanian Dr. Basi V. Subba Reddy 《European journal of organic chemistry》2023,26(13):e202201361
Rh(III)-catalyzed C−H bond annulation of 2-arylquinoxalines with cyclic 2-diazo-1,3-diketones has been accomplished for the first time to synthesize a novel series of 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-one frameworks by means of carbene insertion followed by condensation. The reaction proceeds through the C−H bond activation and functionalization of 2-arylquinoxalines using Rh(III)/AgSbF6 complex to produce highly substituted 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-one and benzo[5,6][1,2,4]thiadiazino[2,3-f]phenanthridin-5(6H)-one-10,10-dioxide derivatives in good to excellent yields. 相似文献
14.
An efficient and mild InBr3-catalyzed approach to synthesize 2,3-dihydroquinazolin-4(1H)-one derivatives (3a–3aa) has been developed. Notably, all the products were isolated by recrystallization and the reaction is accessible on a gram scale. Moreover, the reactions only require 10–60 min. All the synthesized compounds were evaluated for their in vitro anticancer activity against four human cancer cell lines. 相似文献
15.
Shubhangi C. Joshi Kunjbihari N. Trivedi 《Monatshefte für Chemie / Chemical Monthly》1992,123(6-7):557-564
Summary The Claisen rearrangement of 7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 a) gave 7-hydroxy-8-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (3 a) and 2,3-dihydro-2,6-diphenyl-3-methyl-(7H)furo[2,3-h]-1-benzopyran-7-one (7 a). 2-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 b) afforded4 b and7 b. 8-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (12) gave only the alkali soluble product 7-hydroxy-8-methyl-6-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (13).3 a,4 b, and13 were further cyclized in acidic medium to9 a,10 b, and14 followed by dehydrogenation.This paper is dedicated to Dr. F. M. Dean, Department of Organic Chemistry, Robert Robinson Laboratories, University of Liverpool, Liverpool, U. K., on his retirement 相似文献
16.
3,4-Dihydro-5(1H)-pyrromethenones are easier attacked at themeso-position by electrophiles than 5(1H)-pyrromethenones. This is demonstrated both by aMannich-type-substitution or deuterium-exchange-experiments and by the addition of O-, S-, and N-Nucleophiles to the exocyclic double bond of the model-dihydropyrromethenone (Z)-1 under very mild reaction conditions. Applying these results to the chemistry of 2,3-dihydro-bilatrienes-abc, their chemical characteristics—especially their tautomeric behavior and their dominant C-5-selectivity towards electrophiles—become better understandable. 相似文献
17.
2,3‐Dihydro‐4H‐thiopyrano[2,3‐b]pyridin‐4‐ones 4 were prepared by a three‐step sequence from commercially available 2‐chloropyridine ( 1 ). Thus, successive treatment of 1 with iPr2NLi (LDA) and α,β‐unsaturated aldehydes gave 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ols 2 , which were oxidized with MnO2 to 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ones 3 . The reactions of 3 with NaSH?n H2O proceeded smoothly at 0° in DMF to provide the desired thiopyranopyridinones. Similarly, 2,3‐dihydro‐4H‐thiopyrano[2,3‐c]pyridin‐4‐ones 8 and 2,3‐dihydro‐4H‐thiopyrano[3,2‐c]pyridin‐4‐ones 12 were obtained starting from 3‐chloropyridine ( 5 ) and 4‐chloropyridine ( 9 ), respectively. 相似文献
18.
The [3,3′(4H,4′H)‐bi‐2H‐1,3‐oxazine]‐4,4′‐diones 3a – 3i were obtained by [2+4] cycloaddition reactions of furan‐2,3‐diones 1a – 1c with aromatic aldazines 2a – 2d (Scheme 1). So, new derivatives of bi‐2H‐1,3‐oxazines and their hydrolysis products, 3,5‐diaryl‐1H‐pyrazoles 4a – 4c (Scheme 3), which are potential biologically active compounds, were synthesized for the first time. 相似文献
19.
R. Weis U. di Vora W. Seebacher K. Schweiger 《Monatshefte für Chemie / Chemical Monthly》1995,126(12):1367-1374
Summary 6-Phenylimino-3,6-dihydro-2H-thiopyran-4-amines (1) were converted to 1-phenyl-5,6-dihydropyridine-2(1H)-thiones (3). Those were akylated and hydrolyzed, thus yielding 6-methylthio-1-phenyl-2,3-dihydro-4(1H)-pyridinones (5). Finally, the methylthio group was removed withRaney nickel giving the title compounds6. The relative configurations of the formed diastereoisomeric dihydropyridinones have been investigated by NOE measurements.
Umwandlung von 6-Phenylimino-2H-thiopyran-4-aminen zu 1-Phenyl-2,3-dihydro-4(1H)-pyridinonen
Zusammenfassung 6-Phenylimino-3,6-dihydro-2H-thiopyran-4-amine (1) wurden in 1-Phenyl-5,6-dihydropyridin-2(1H)-thione (3) umgewandelt. Diese wurden alkyliert und zu 6-Methylthio-1-phenyl-2,3-dihydro-4(1H)-pyridinonen (5) hydrolysiert. Zuletzt gelangte man durch selektives Entfernen der Methylthiogruppe mitRaney-Nickel zu den Titelverbindungen6. Die relativen Konfigurationen der gebildeten diastereomeren Dihydropyridinone wurden durch NOE-Messungen aufgeklärt.相似文献
20.
Chikkanti Jaganmohan Vinay Kumar K. P. Sandeep Reddy G. Sandeep Mohanty Jaydeep Kumar Venkateswara Rao B. 《合成通讯》2018,48(2):168-174
A new versatile and efficient strategy for the synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazoline-4(1H)-one compounds has been developed by one-pot multicomponent reaction with isatoic anhydride, amines followed by in situ-generated Vilsmeier reagent. The reaction has also been studied with different amines and solvents. 相似文献