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Abdelmejid Bahloul Abdelfatah Sebban Zainaba Dardari Mohammed Boudouma Said Kitane Touria Belghiti Jean‐Pierre Joly 《Journal of heterocyclic chemistry》2003,40(2):243-248
Diarylnitrilimine and arylnitriloxide dipoles react with two 8‐hydroxyquinoline substrates to give respectively pyrazolinic and isoxazolinic derivatives. The structure of these new heterocycles was established on the basis of their spectroscopic data and by chemical methods. The inhibition activity of one of these heterocycles was evaluated in vitro against 8 pathogenic μ‐organisms. 相似文献
3.
Metallacyclopentadienes and related heterocycles via 1,1‐organoboration of alkyn‐1‐ylmetal compounds
Bernd Wrackmeyer 《Heteroatom Chemistry》2006,17(3):188-208
Metallacyclopentadienes (metalloles) containing M = Si, Ge, Sn, Pb, Ti, Pt can be prepared by 1,1‐organoboration of alkyn‐1‐ylmetal compounds LnM CC R1(R1 = H, alkyl, aryl, silyl, etc; L depends on M, and can be hydrogen, alkyl, aryl, Cl, Br, amino groups, a chelating diphosphane, and one or more L can be again alkynyl groups). These reactions proceed via activation of the M C bond(s) by an electron‐deficient triorganoborane BR3 (R = alkyl, aryl; non‐cyclic, monocyclic, bicyclic, and tricyclic boranes), at first intermolecular and then intramolecular. In the course of these reactions, the M C bonds are cleaved, zwitterionic alkynylborate‐like intermediates are formed, in which the metal‐containing fragments are coordinated side‐on to the CC bonds. In most cases, the 1,1‐organoboration reactions tolerate various functional groups at the alkyne as well as at the metal. The characterization of intermediates and final products by X‐ray structural analysis and by multinuclear magnetic resonance spectroscopy (NMR) is documented and described. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:188–208, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20222 相似文献
4.
Synthesis of Some New Pyrazole,Pyrimidine, Pyridazine,and Their Fused Derivatives from 3‐Oxo‐3,N‐diphenylpropionamide 下载免费PDF全文
Fathy M. Abdelrazek Yehia M. Elkholy Ali M. Salah Nagwa M. Abdelazeem Peter Metz 《Journal of heterocyclic chemistry》2014,51(3):824-829
The title compounds were obtained from the reactions of 3‐oxo‐3,N‐diphenylpropionamide 3 with dimethylformamide dimethylacetal followed by hydrazine to afford the pyrazole 7 , condensation with benzaldehyde followed by cyclocondensation with guanidine to afford the pyrimidine derivative 13 , condensation with active methylenes followed by azo coupling of the products followed by cyclization to afford the pyridazines 17a , 17b . The pyridazinone 17b was explored for the synthesis of some novel pyridazine‐fused heterocyclic compounds 19 , 21 , 24a , 24b , 24c , and 26 . All structures were proved via their elemental analyses and spectral data. 相似文献
5.
《Journal of heterocyclic chemistry》2017,54(1):670-676
Using 3‐(4‐cyano phenoxy)‐6‐methyl‐4‐(3‐trifluoromethylphenyl) pyridazine (compound A ) as a leading compound, a total of 24 novel 3‐(substituted phenoxy)‐6‐methyl‐4‐(3‐trifluoromethylphenyl) pyridazine derivatives containing two electron‐withdrawing groups on the benzene ring (acylamine and oxime ether) were synthesized. Their herbicidal, insecticidal activities were bioassayed, and the herbicidal activity of compound CD-2 against Brassica campestris was 97.6% at 300 g/ha, which was better than the commercial herbicide diflufenican at the this concentration and is equal to the activity of the leading compound A . Compound CD-4 , CD-5 , CJ-3 , and CJ-5 displayed excellent insecticidal activity against Aphis laburni Kaltenbach (>95%). The results show that the oxime ether substitutions exhibit better bleaching and herbicidal activity than the acylamine ones. The bleaching and herbicidal activity of para‐position substitutions is better than the meta‐position ones. It seems that the para‐position on the benzene ring of oxime ether pyridazine derivatives is one of the key active sites that affect their herbicidal activities. 相似文献
6.
Yoshiko Miyamoto 《Journal of heterocyclic chemistry》2002,39(1):157-162
The direct annelation reaction of 4‐substituted 2‐amino‐l‐benzylideneamino‐1H‐imidazoles ( 1 ) or 2‐amino‐1‐isopropylideneamino‐1H‐imidazole ( 8 ) with ethoxymethylenemalononitrile ( I ) gave successfully bicyclic imidazo[1,2‐a]pyrimidine compounds 2 and 9 in high yields. The reactions of other ethoxymethylene compounds of lower reactivity, i.e., ethyl ethoxymethylenecyanoacetate ( II ) and diethyl ethoxymethylenemalonate ( III ), with 2‐amino‐1H‐imidazoles under similar conditions afforded the corresponding enamines 3, 4 and 10 , which, upon heating in the presence of an acid or a base, could readily be cyclized to form imidazopyrimidines except for 1‐isopropylideneamino compound 10 . In general, the 3‐phenyl compounds ( 3b and 4b ) did not cyclize to the type 2 compound resulting in a full recovery of the starting enamines. 相似文献
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Rates and products of reaction and Arrhenius activation parameters were determined for the gas‐phase thermolysis of 14 substrates of the title compounds using sealed pyrex reactor tubes and HPLC/UV‐VIS to monitor substrate pyrolysis. The 14 compounds under study are N‐phenyl‐3‐oxo‐ ( 1 ), N‐(p‐chlorophenyl)‐3‐oxo‐ ( 2 ), N‐(p‐methylphenyl)‐3‐oxo‐ ( 3 ), and N‐(p‐methoxyphenyl)‐3‐oxobutanamide ( 4 ), in addition to (i) four substrates ( 5–8 ) obtained by the replacement of the pairs of methylene hydrogens at the 2‐position of compounds ( 1–4 ), each pair by a phenylhydrazono group; (ii) three arylhydrazono derivatives ( 9–11 ) in which Cl, CH3, or OCH3 groups are substituted at the para position of the phenylhydrazono moiety of compound 5 ; (iii) 3‐oxobutanamide (acetoacetamide, 12 ), N‐phenyl‐3‐oxo‐3‐phenylpropanamide ( 13 ), and N,N′‐diphenylpropanediamide ( 14 ). The reactions were conducted over 374–546 K temperature range, and the values of the Arrhenius log A(s?1) and Ea(kJ mol?1) of these reactions were, respectively, 12.0 ± 2.0 and 119.2 ± 17.0 for the ketoanilides ( 1–4, 12–14 ), and 13.0 ± 0.7 and 157.5 ± 8.6 for the arylhyrazono compounds ( 5–11 ). Kinetically, the arylhydrazono derivatives were found to be ca. 1.4 × 103 to 5.7 × 103 times less reactive than the parent ketoanilides. A mechanism is proposed to account for reaction products and to rationalize molecular reactivities. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 39: 82–91, 2007 相似文献
8.
Abdellatif M. Salah Eldin 《Heteroatom Chemistry》2003,14(7):612-616
2‐Amino‐1,1,3‐tricyano‐3‐bromopropene was obtained from bromination of 2‐amino‐1,1,3‐tricyanopropene (malononitrile dimer) with N‐bromosuccinimide. This bromo derivative reacts with hydrazine hydrate, phenyl hydrazine, and hydroxylamine hydrochloride to afford pyridazine and oxazine derivatives, respectively. In base‐catalyzed reactions with primary aromatic amines and anthranilic acid derivatives, it produces N‐aryl pyrrol‐3,5‐dicarbonitrile and pyrrolo[1,2‐a]quinazolin‐5‐imine, or pyrrolo[1,2‐a]quinazolin‐5‐one derivatives, respectively. The structures of the newly synthesized heterocycles were established on the basis of elemental analyses and spectral data. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:612–616, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10199 相似文献
9.
Alexandre Bridoux Laurence Goossens Raymond Houssin Jean‐Pierre Hanichart 《Journal of heterocyclic chemistry》2006,43(3):571-578
The Fischer reaction is applied to the synthesis of 8‐substituted tetrahydro‐γ‐carbolines with electron‐donating or electron‐withdrawing groups, using catalytic or thermal methods. The reaction conditions must be varied according to the nature of the N 1 substituent of the piperidone. The best results are observed when a releasing group is present on the arylhydrazine and a benzyl substituent on the nitrogen of piperidone. Formation of carbolines with a withdrawing substituent is observed in soft acidic conditions; in others, reaction ended at the hydrazone level or did not evolve. 相似文献
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Swetha Yagnam Eda Rami Reddy Rajiv Trivedi Narra Vamshi Krishna Lingamallu Giribabu Balaji Rathod Reddy Shetty Prakasham Balasubramanian Sridhar 《应用有机金属化学》2019,33(4)
A series of bioactive, triazole‐linked benzyl, aryl, sugar and aliphatic conjugates of 3‐ferrocenylidene‐oxindole have been synthesized. A facile 1,3‐dipolar‐Huisgen coupling reaction of the respective azides with the 3‐ferrocenylidene‐oxindole N‐propargyl moiety ( 3 ) gave the corresponding conjugates ( 5a–n ). All the newly synthesized compounds ( 5a–n ) were characterized by 1H‐NMR, 13C‐NMR, HRMS, Fourier transform‐infrared spectroscopy and elemental analysis. The UV–Vis and electrochemical studies of these compounds were performed in dimethylsulfoxide solutions. The structure of compound ( 3 ) was determined by single crystal X‐ray diffraction study. These compounds exhibited moderate to good antimicrobial activity against Gram‐positive and Gram‐negative strains. 相似文献
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3‐Alkylcarbonyloxymethyl derivatives of 5‐fluorouracil have been synthesized starting with 1‐ethyloxy‐carbonyl‐5‐fluorouracil. Alkylation of the starting material with alkylcarbonyloxymethyl iodides, generated from the corresponding chlorides by the Finkelstein reaction, in the presence of 1,8‐bis(dimethyl‐amino)naphthalene followed by deprotection with 1,1‐dimethylethylamine gave good yields (50‐60%) of the target derivatives after column chromatography. A 90% yield of 3‐acetyloxymethyl‐5‐fluorouracil was obtained when the corresponding commercially available bromide was used, instead of the in situ generated iodide, and the product could be isolated from the crude reaction by crystallization. An alternate path of sequential alkylation of 5‐fluorouracil with alkylcarbonyloxymethyl chlorides in the presence of tertiary amines, exhibiting different reactivities towards the chlorides, gave an excellent yield of 1‐acetyloxymethyl‐3‐propionyloxymethyl‐5‐fluorouracil in the one instance it was attempted, but subsequent deprotection of the 1‐position with methylamine gave only a 24% yield of 3‐propionyloxymethyl‐5‐fluorouracil. 相似文献
12.
O. Mansour B. Szymonski J. M. Morand M. Cussac F. Thomasson 《Journal of heterocyclic chemistry》2001,38(3):641-643
A series of 3‐carboxylic derivatives of disubstituted 1,5‐benzodiazepines (5–9) was synthesized by hetero‐cyclisation from 1,2‐diaminobenzene (1) with dibenzoylmethane (2) followed by bromination on position 3 and by introduction of the carboxylic group or introduction of the malonic moiety. Reduction of the hetero‐cycle gave the perhydro derivative diethyl (2,4‐diphenyl‐1,2,4,5‐tetrahydro‐3H‐1,5‐benzodiazepin‐3‐yl)malonate (9) . 相似文献
13.
Wolfgang Stadlbauer Anna E. Tubl Hoai V. Dang Claudia Reidlinger Klaus Zangger 《Journal of heterocyclic chemistry》2006,43(1):117-125
4‐Chloro‐ or 4‐tosyloxyquinolines 1 and 10 react with CH‐acidic compounds such as malonates 2a,b , ethyl cyanoacetate ( 2c ), malononitrile ( 2d ), ethyl acetoacetate ( 2e ), acetylacetone ( 2f ) or dimedone ( 2g ) under mild conditions and good yields to quinolin‐4‐yl substituted derivatives 3‐8 and 11 . With 3‐phenylsulfonylquinolones 1i‐k a redox reaction to 2‐hydroxy‐2‐quinolin‐4‐yl‐malonates 9 was observed. Amination of 3‐nitroquinolinyl malonate 3f leads to malonester‐amides 13 and 14 . 相似文献
14.
The syntheses and characterisation of a series of chiral and achiral 2‐(aminophenyl)‐2‐oxazolines and some related compounds is reported. All of the derivatives have been produced by a one‐step procedure involving the treatment of isatoic anhydride (i.e. [2H]‐3, 1‐benzoxazine‐[1H‐2,4‐dione: 1 ) or its 5‐chloro analogue with a slight excess of appropriate amino‐alcohols. In most cases, anhydrous ZnCl2 is shown to be an effective Lewis acid catalyst for this reaction at reflux temperature in high boiling aromatic solvents (PhCl or PhMe). Oxazolines have been readily formed using rac‐2‐amino‐1‐butanol, (S)‐phenylglycinol, 2‐methyl‐2‐amino‐1‐propanol and (1S,2R) or (IR,2S)‐cis‐ 1 ‐amino‐2‐indanol; yields range from 85% to 22%. The use of aminoalcohols such as 2‐ethanolamine, (±)‐2‐amino‐1‐phenyl‐1‐propanol or 3‐amino‐1‐propanol (to give the corresponding 4,5‐dihydro‐1,3‐oxazine) results in poor yields. The use of other Lewis acid catalysts (silicic acid, Cd(acac)2·2H2O, CuCl2·2H2O, InCl3) or higher temperatures did not improve the yields with these latter two substrates. Benzoxazoles and N‐substituted benzoxazoles can also be obtained in reasonable yields from 1 using 2‐aminophenol (36%) or 2‐amino‐3‐hydroxypyridine (45%). 相似文献
15.
1‐Aroyl‐2‐styrylsulfonylethene is the precursor for 4,4‐dimethoxycarbonyl‐2′,5‐diaryl‐3‐(1′,3′‐dioxolano)‐1‐thia‐1,1‐dioxide ( 4 ), which is the key intermediate for the synthesis of 7‐aroyl‐11‐aryl‐2,4‐diazaspiro[5,5]undecane‐1,3,5‐trione‐9‐thia‐9,9‐dioxide( 10 )/3‐thioxo‐1,5‐dione‐9‐thia‐9,9‐dioxide ( 11 ), 6‐aroyl‐10‐aryl‐2,3‐diazaspiro[4,5]decane‐1,4‐dione‐8‐thia‐8,8‐dioxide ( 12 )/2‐oxo‐3‐azaspiro [4,5]decane‐1,4‐dione‐8‐thia‐8,8‐dioxide ( 13 ). The new compounds were characterized by IR and 1H NMR spectral data. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:131–135, 2001 相似文献
16.
Kazuko Shirai Koushi Fukunishi Atsushi Yanagisawa Hiroshi Takahashi Masaru Matsuoka 《Journal of heterocyclic chemistry》2000,37(5):1151-1156
The reaction of 2,5‐diamino‐3,6‐dicyanopyrazine ( 1 ) as a new pyrazine raw material with alkyl isocyanate in the presence of sodium hydride gave novel heptahydroirnidazo[4,5‐g]pteridine‐2,6,8‐trione ( 2 ), but with tertiary butyl isocyanate gave trihydroimidazo[4,5‐b]pyrazine‐2‐ones ( 3 ). Similar reaction of 1 with alkyl thioisocyanate followed by alkyl iodide gave tetrahydropyrimido[4,5‐g]pteridines ( 4 ). The reac tion of 1 with alkylamine gave the amine‐adduct of the cyano groups which was further reacted with arylaldehyde to give the pyrimido[4,5‐g]pteridine ( 10 ). The products prepared are all of interest as potential pesticides and fluorescent chromophores. 相似文献
17.
Sohail Saeed Naghmana Rashid Peter G. Jones Arifa Tahir 《Journal of heterocyclic chemistry》2011,48(1):74-82
A series of new N‐Substituted‐N′‐(4,6‐dimethylpyrimidin‐2‐yl)‐thiourea derivatives ( 3a , 3b , 3c , 3d ) and related fused heterocyclic compounds ( 4a , 4b , 4c , 4d ) were synthesized using tetrabutylammonium bromide as phase transfer catalyst (PTC). N‐[(2E)‐5,7‐dimethyl‐2H‐[1,2,4] thiadiazolo [2,3‐a] pyrimidin‐2‐ylidene] derivatives ( 4a , 4b , 4c , 4d ) were prepared by oxidative cyclization of 3a , 3b , 3c , 3d . The structures of these novel compounds were characterized by IR, 1H NMR, 13C NMR, mass spectrometry, and the elemental analysis. The crystal structures were determined from single crystal X‐ray diffraction data. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bacteria. Compounds 3d and 3a exhibited the greatest antimicrobial activity. J. Heterocyclic Chem., 2011. 相似文献
18.
Leyte Winfield Chunming Zhang Christy A. Reid Edwin D. Stevens Mark L. Trudell Sari Izenwasser Dean Wade 《Journal of heterocyclic chemistry》2003,40(5):827-832
A series of 2,5‐disubstituted 1,3,5‐dithiazine derivatives were synthesized as potential analogues of the potent dopamine uptake inhibitor GBR 12909. The lipophilic character of the 1,3,5‐dithiazine derivatives were experimentally (log P) and computationally (clog P) determined. The in vitro binding affinities of the 2,5‐disubstituted 1,3,5‐dithiazine derivatives at the dopamine transporter were determined to be much less potent than the binding affinity of GBR 12909 due to steric and electronic effects inherent to the 1,3,5‐dithiazine ring system. The X‐ray crystal structure of 2‐(2‐[bis(4‐fluorophenyl)methoxy]ethyl)‐5‐(3‐phenylpropyl)‐1,3,5‐dithiazine (7) revealed that the 5‐(3‐phenylpropyl) group is in a pseudo‐axial orientation and syn to the 2‐ethoxybenzhydryl moiety. 相似文献
19.
《Journal of heterocyclic chemistry》2017,54(1):473-479
Arylhydrazones are prepared and reacted with pyrazolylmethylene malononitrile derivatives yielding 2,5‐dihydropyridazines substituted at C‐5 by pyrazole derivatives. Utilizing azaenamine containing a cyano group at the ortho position enabled the formation of the condensed pyridazino[1,6‐a ]quinazoline derivatives. A subsequent acetylation of the synthesized pyridazines led to the formation of pyrimido[4,5‐c ]pyridazine compounds which can be considered as 4‐deazatoxoflavin derivatives. All the new compounds were full‐characterized by the different spectral tools and the unambiguous structural elucidation of 2,5‐dihydropyridazines was done using 2D‐HMBC spectroscopy 相似文献
20.
Francesco Foti Giovanni Grassi Francesco Risitano Salvatore La Rosa 《Journal of heterocyclic chemistry》2001,38(2):539-540
The synthesis of a series of 3‐Imidazolylazole derivatives using cycloaddition reactions of a useful new nitrile oxide is described. 相似文献