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1.
Mohamed A. Saleh Yehia A. Hafez Foad E. Abdel‐Hay Wagdy I. Gad 《Journal of heterocyclic chemistry》2003,40(6):973-978
The reaction of 3‐N‐(2‐mercapto‐4‐oxo‐4H‐quinazolin‐3‐yl)acetamide ( 1 ) with hydrazine hydrate yielded 3‐amino‐2‐methyl‐3H‐[1,2,4]triazolo[5,1‐b]quinazolin‐9‐one ( 2 ). The reaction of 2 with o‐chlorobenzaldehyde and 2‐hydroxy‐naphthaldehyde gave the corresponding 3‐arylidene amino derivatives 3 and 4 , respectively. Condensation of 2 with 1‐nitroso‐2‐naphthol afforded the corresponding 3‐(2‐hydroxy‐naphthalen‐1‐yl‐diazenyl)‐2‐methyl‐3H‐[1,2,4]triazolo[5,1‐b]quinazolin‐9‐one ( 5 ), which on subsequent reduction by SnCl2 and HCl gave the hydrazino derivative 6. Reaction of 2 with phenyl isothiocyanate in refluxing ethanol yielded thiourea derivative 7. Ring closure of 7 subsequently cyclized on refluxing with phencyl bromide, oxalyl dichloride and chloroacetic acid afforded the corresponding thiazolidine derivatives 8, 9 and 10 , respectively. Reaction of 2‐mercapto‐3‐phenylamino‐3H‐quinazolin‐4‐one ( 11 ) with hydrazine hydrate afforded 2‐hydrazino‐3‐phenylamino‐3H‐quinazolin‐4‐one ( 12 ). The reactivity 12 towards carbon disulphide, acetyl acetone and ethyl acetoacetate gave 13, 14 and 15 , respectively. Condensation of 12 with isatin afforded 2‐[N‐(2‐oxo‐1,2‐dihydroindol‐3‐ylidene)hydrazino]‐3‐phenylamino‐3H‐quinazolin‐4‐one ( 16 ). 2‐(4‐Oxo‐3‐phenylamino‐3,4‐dihydroquinazolin‐2‐ylamino)isoindole‐1,3‐dione ( 17 ) was synthesized by the reaction of 12 with phthalic anhydride. All isolated products were confirmed by their ir, 1H nmr, 13C nmr and mass spectra. 相似文献
2.
An efficient one‐pot synthesis of 3‐[(4,5‐dihydro‐1H‐pyrrol‐3‐yl)carbonyl]‐2H‐chromen‐2‐one (=3‐[(4,5‐dihydro‐1H‐pyrrol‐3yl)carbonyl]‐2H‐1‐benzopyran‐2‐one) derivatives 4 by a four‐component reaction of a salicylaldehyde 1 , 4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one, a benzylamine 2 , and a diaroylacetylene (=1,4‐diarylbut‐2‐yne‐1,4‐dione) 3 in EtOH is reported. This new protocol has the advantages of high yields (Table), and convenient operation. The structures of these coumarin (=2H‐1‐benzopyran‐2‐one) derivatives, which are important compounds in organic chemistry, 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
3.
Cherng‐Chyi Tzeng I.‐Li Chen Yeh‐Long Chen Tai‐Chi Wang Ya‐Ling Chang Che‐Ming Teng 《Helvetica chimica acta》2000,83(2):349-358
In continuation of our search for potent antiplatelet agents, we have synthesized and evaluated several α‐methylidene‐γ‐butyrolactones bearing 3,4‐dihydroquinolin‐2(1H)‐one moieties. O‐Alkylation of 3,4‐dihydro‐8‐hydroxyquinolin‐2(1H)‐one ( 1 ) with chloroacetone under basic conditions afforded 3,4‐dihydro‐8‐(2‐oxopropoxy)quinolin‐2(1H)‐one ( 2a ) and tricyclic 2,3,6,7‐tetrahydro‐3‐hydroxy‐3‐methyl‐5H‐pyrido[1,2,3‐de][1,4]benzoxazin‐5‐one ( 3a ) in a ratio of 1 : 2.84. Their Reformatsky‐type condensation with ethyl 2‐(bromomethyl)prop‐2‐enoate furnished 3,4‐dihydro‐8‐[(2,3,4,5‐tetrahydro‐2‐methyl‐4‐methylidene‐5‐oxofuran‐2‐yl)methoxy]quinolin‐2(1H)‐one ( 4a ), which shows antiplatelet activity, in 70% yield. Its 2′‐Ph derivatives, and 6‐ and 7‐substituted analogs were also obtained from the corresponding 3,4‐dihydroquinolin‐2(1H)‐ones via alkylation and the Reformatsky‐type condensation. Of these compounds, 3,4‐dihydro‐7‐[(2,3,4,5‐tetrahydro‐4‐methylidene‐5‐oxo‐2‐phenylfuran‐2‐yl)methoxy]quinolin‐2(1H)‐one ( 10b ) was the most active against arachidonic acid (AA) induced platelet aggregation with an IC50 of 0.23 μM . For the inhibition of platelet‐activating factor (PAF) induced aggregation, 6‐{[2‐(4‐fluorophenyl)‐2,3,4,5‐tetrahydro‐4‐methylidene‐5‐oxofuran‐2‐yl]methoxy}‐3,4‐dihydroquinolin‐2(1H)‐one ( 9c ) was the most potent with an IC50 value of 1.83 μM . 相似文献
4.
Diana Becerra Braulio Insuasty Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2010,66(2):o79-o86
The molecules of racemic 3‐benzoylmethyl‐3‐hydroxyindolin‐2‐one, C16H13NO3, (I), are linked by a combination of N—H...O and O—H...O hydrogen bonds into a chain of centrosymmetric edge‐fused R22(10) and R44(12) rings. Five monosubstituted analogues of (I), namely racemic 3‐hydroxy‐3‐[(4‐methylbenzoyl)methyl]indolin‐2‐one, C17H15NO3, (II), racemic 3‐[(4‐fluorobenzoyl)methyl]‐3‐hydroxyindolin‐2‐one, C16H12FNO3, (III), racemic 3‐[(4‐chlorobenzoyl)methyl]‐3‐hydroxyindolin‐2‐one, C16H12ClNO3, (IV), racemic 3‐[(4‐bromobenzoyl)methyl]‐3‐hydroxyindolin‐2‐one, C16H12BrNO3, (V), and racemic 3‐hydroxy‐3‐[(4‐nitrobenzoyl)methyl]indolin‐2‐one, C16H12N2O5, (VI), are isomorphous in space group P. In each of compounds (II)–(VI), a combination of N—H...O and O—H...O hydrogen bonds generates a chain of centrosymmetric edge‐fused R22(8) and R22(10) rings, and these chains are linked into sheets by an aromatic π–π stacking interaction. No two of the structures of (II)–(VI) exhibit the same combination of weak hydrogen bonds of C—H...O and C—H...π(arene) types. The molecules of racemic 3‐hydroxy‐3‐(2‐thienylcarbonylmethyl)indolin‐2‐one, C14H11NO3S, (VII), form hydrogen‐bonded chains very similar to those in (II)–(VI), but here the sheet formation depends upon a weak π–π stacking interaction between thienyl rings. Comparisons are drawn between the crystal structures of compounds (I)–(VII) and those of some recently reported analogues having no aromatic group in the side chain. 相似文献
5.
Divvela V. N. Srinivasa Rao Ganala Naga Trinadhachari Koilpillai Joseph Prabahar Ramesh Dandala Meenakshisundaram Sivakumaran Andra Naidu 《Journal of heterocyclic chemistry》2007,44(3):663-667
6.
A one‐step ‘ring switching’ transformation of (S)‐3‐[(dimethylamino)methylidene]‐5‐(methoxycarbonyl)tetrahydrofuran‐2‐one ( 4 ) with 2‐pyridineacetic acid derivatives ( 5–7 ) and 2‐aminopyridines ( 8, 9 ) afforded the corresponding 3‐(4‐oxo‐4H‐quinolizinyl‐3)‐ (15–17) and 3‐(4‐oxo‐4H‐pyridino[1,2‐a]pyrimidinyl‐3)‐2‐hydroxypropanoates ( 18, 19 ), respectively. 相似文献
7.
Deepak Chopra T. P. Mohan B. Vishalakshi T. N. Guru Row 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(12):o704-o710
In the molecular structures of a series of substituted chalcones, namely (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐phenylprop‐2‐en‐1‐one, C21H15FO2, (I), (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐(4‐fluorophenyl)prop‐2‐en‐1‐one, C21H14F2O2, (II), (2E)‐1‐(4‐chlorophenyl)‐3‐(2‐fluoro‐4‐phenoxyphenyl)prop‐2‐en‐1‐one, C21H14ClFO2, (III), (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐(4‐methylphenyl)prop‐2‐en‐1‐one, C22H17FO2, (IV), and (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐(4‐methoxyphenyl)prop‐2‐en‐1‐one, C22H17FO3, (V), the configuration of the keto group with respect to the olefinic double bond is s‐cis. The molecules pack utilizing weak C—H...O and C—H...π intermolecular contacts. Identical packing motifs involving C—H...O interactions, forming both chains and dimers, along with C—H...π dimers and π–π aromatic interactions are observed in the fluoro, chloro and methyl derivatives. 相似文献
8.
Ch. Sanjeeva Reddy M. Vani Devi G. Rajesh Kumar L. Sanjeeva Rao A. Nagaraj 《Journal of heterocyclic chemistry》2011,48(1):176-182
A series of novel 2‐(aryl)‐3‐[5‐(2‐oxo‐2H‐3‐chromenyl)‐1,3‐oxazol‐2‐yl]‐1,3‐thiazolan‐4‐ones 4a , 4b , 4c , 4e , 4f , 4g , 4h , 4i , 4j have been synthesized and assayed for their antibacterial activity against Gram‐positive bacteria viz. Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), Micrococcus luteus (IFC 12708), and Gram‐negative bacteria viz. Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), Escherichia coli (ATCC 25922), and also antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). Among the screened compounds, 4d , 4e , 4f , 4g , and 4j exhibited potent inhibitory activity compared with the standard drug at the tested concentrations. The results reveal that, the presence of difluorophenyl in 4f and pipernyl ring in 4j at 2‐position of thiazolidine‐4‐one ring show significant inhibitory activity. The other compounds also showed appreciable activity against the test bacteria and fungi and emerged as potential molecules for further development. J. Heterocyclic Chem., 2011. 相似文献
9.
Shan Gao Zhen‐Zhong Lu Li‐Hua Huo Hui Zhao 《Acta Crystallographica. Section C, Structural Chemistry》2004,60(12):m651-m653
The title complex, [Ag(C5H4NO)(C5H5NO)]n, consists of a polymeric neutral chain involving both a neutral pyridin‐4‐ol ligand and a deprotonated pyridin‐4‐olate monoanion. The AgI atom shows a T‐shaped coordination geometry, defined by one N atom of the pyridin‐4‐ol and one O and one N atom of two independent pyridin‐4‐olate bridges; the N—Ag—N moiety is approximately linear. The polymeric chains are connected via strong O—H⋯O hydrogen bonds and offset π–π interactions into a three‐dimensional network. 相似文献
10.
Jzsef Deli Erzsbet
sz Júlia Visy Ferenc Zsila Mikls Simonyi Gyula Tth 《Helvetica chimica acta》2001,84(1):263-270
The (3R,5′R,6′R)‐ and (3R,5′R,6′S)‐capsanthol‐3′‐one (=3,6′‐dihydroxy‐β,κ‐caroten‐3′‐one; 4 and 5 , resp.) were reduced by different complex metal hydrides containing organic ligands. The ratio of the thus obtained diastereoisomeric (3′S)‐capsanthols 2 and 3 or (3′R)‐capsanthols 6 and 7 , respectively, was investigated. Four complex hydrides showed remarkable stereoselectivity and produced the (3′R,6′S)‐capsanthol ( 6 ) in 80 – 100% (see Table 1). The starting materials and the products were characterized by UV/VIS, CD, 1H‐ and 13C‐NMR, and mass spectra. 相似文献
11.
Zdenko Hamerak Dajana Gao Spomenka Kova
Antonija Hergold‐Brundi Ivan Vickovi Vitomir unji 《Helvetica chimica acta》2003,86(6):2247-2257
Aldol reaction of 7‐chloro‐1,3‐dihydro‐1‐methyl‐5‐phenyl‐2H‐1,4‐benzodiazepin‐2‐one ( 1 ) with 4‐substituted α‐methylcinnamaldehydes 2 – 5 afforded a mixture of threo‐ and erythro‐3‐(3‐aryl‐1‐hydroxy‐2‐methylprop‐2‐enyl)‐7‐chloro‐1,3‐dihydro‐1‐methyl‐5‐phenyl‐2H‐1,4‐benzodiazepin‐2‐ones 6 – 13 . The chromatographically separated threo diastereoisomers 6, 8, 10 , and 12 and erythro diastereoisomers 7, 9, 11 , and 13 were submitted to ‘directed' homogeneous hydrogenation catalyzed by [RhI(cod)(diphos‐4)]ClO4 (cod=cycloocta‐1,5‐diene, diphos‐4=butane‐1,4‐diylbis[diphenylphosphine]. From the erythro‐racemates 9, 11 , and 13 , the erythro,erythro/erythro,threo‐diastereoisomer mixtures 16 / 17, 20 / 21 , and 24 / 25 were obtained in ratios of 20 : 80 to 28 : 72 (HPLC), which were separated by chromatography. From the threo racemates 8, 10 , and 12 , the threo,threo/threo,erythro‐diastereoisomer mixtures were obtained in a ratio of ca. 25 : 75 (1H‐NMR). The relative configurations were assigned by means of 1H‐NMR data and X‐ray crystal‐structure determination of 21 . Hydrolysis of 21 afforded the diastereoisomerically pure N‐(benzyloxy)carbonyl derivative 27 of α‐amino‐β‐hydroxy‐γ‐methylpentanoic acid 26 , representative of the novel group of polysubstituted α‐amino‐β‐hydroxycarboxylic acids. 相似文献
12.
《Journal of heterocyclic chemistry》2017,54(4):2258-2265
The present study emphasizes on the dealklylation of 3‐aryl‐5‐alkyl‐2‐oxo‐Δ4‐1,3,4‐oxadiazoles when reacted with formamide resulting in the formation of 2‐aryl‐2H‐1,2,4‐triazol‐3(4H )‐ones as major product. Subsequent reactions of 2‐aryl‐2H‐1,2,4‐triazol‐3(4H )‐one gave triazolo[3,4‐b ][1,3,4]thiadiazoles and triazolo[3,4‐b ][1,3,4]thiadiazines derivatives incorporated with 1,2,4‐triazol‐3‐one. 相似文献
13.
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
14.
Kate J. Akerman Orde Q. Munro 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(3):258-262
The Schiff base enaminones (3Z)‐4‐(5‐ethylsulfonyl‐2‐hydroxyanilino)pent‐3‐en‐2‐one, C13H17NO4S, (I), and (3Z)‐4‐(5‐tert‐butyl‐2‐hydroxyanilino)pent‐3‐en‐2‐one, C15H21NO2, (II), were studied by X‐ray crystallography and density functional theory (DFT). Although the keto tautomer of these compounds is dominant, the O=C—C=C—N bond lengths are consistent with some electron delocalization and partial enol character. Both (I) and (II) are nonplanar, with the amino–phenol group canted relative to the rest of the molecule; the twist about the N(enamine)—C(aryl) bond leads to dihedral angles of 40.5 (2) and −116.7 (1)° for (I) and (II), respectively. Compound (I) has a bifurcated intramolecular hydrogen bond between the N—H group and the flanking carbonyl and hydroxy O atoms, as well as an intermolecular hydrogen bond, leading to an infinite one‐dimensional hydrogen‐bonded chain. Compound (II) has one intramolecular hydrogen bond and one intermolecular C=O...H—O hydrogen bond, and consequently also forms a one‐dimensional hydrogen‐bonded chain. The DFT‐calculated structures [in vacuo, B3LYP/6‐311G(d,p) level] for the keto tautomers compare favourably with the X‐ray crystal structures of (I) and (II), confirming the dominance of the keto tautomer. The simulations indicate that the keto tautomers are 20.55 and 18.86 kJ mol−1 lower in energy than the enol tautomers for (I) and (II), respectively. 相似文献
15.
《Journal of heterocyclic chemistry》2017,54(6):3321-3330
3‐(4‐hydroxy‐1‐methylquinoline‐3‐yl)‐3‐oxoproponal ( 5 ) was synthesized from 3‐[(E)‐3‐(dimethylamino)‐2‐propenoyl]‐4‐hydroxy‐1‐methyl‐2(1H )‐quinolinone ( 3 ) and was utilized as a starting precursor material. A convenient new route to functionalized 3‐heterocyclyl 4‐hydroxy‐2(1H )‐quinolinones such as pyrazolyl, isoxazolyl, pyrimidinyl, azepineyl , pyridonyl, and pyranyl heterocycles was described via cyclization of compound 5 with some N and C ‐nucleophiles. The newly synthesized aldehyde 5 showed only one ring closure possibility with maximum yield instead of using compound 3 that exhibited different regioselective ring closure routes with minimum yields. All newly synthesized products were structurally elucidated on the basis of their relevant spectroscopic data and elemental microanalyses. The antioxidant activity of the products was screened in a series of in vitro tests. 相似文献
16.
Shan Hou Qi‐Kui Liu Yan‐An Li Jian‐Ping Ma Yu‐Bin Dong 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(10):1108-1111
2,5‐Bis[4‐methyl‐3‐(pyridin‐3‐yl)phenyl]‐1,3,4‐oxadiazole (L), C26H20N4O, forms one‐dimensional chains via two types of intermolecular π–π interactions. In catena‐poly[[dichloridozinc(II)]‐μ‐2,5‐bis[4‐methyl‐3‐(pyridin‐3‐yl)phenyl]‐1,3,4‐oxadiazole], [ZnCl2(C26H20N4O)]n, synthesized by the combination of L with ZnCl2, the ZnII centres are coordinated by two Cl atoms and two N atoms from two L ligands. [ZnCl2L]n forms one‐dimensional P (plus) and M (minus) helical chains, where the L ligand has different directions of twist. The helical chains stack together via interchain π–π and C—H...π interactions. 相似文献
17.
Synthesis of 1‐Amino‐5,6‐diaryl‐3‐cyano‐1H‐pyridin‐2‐ones and 6,7‐Diaryl‐4‐cyano‐3‐hydroxy‐1H‐[1,2]diazepines from Isoflavones
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Mu‐Lin Zhu Zun‐Ting Zhang Dong Xue Hui‐Liang Hua Yong Liang Stanislaw F. Wnuk 《Helvetica chimica acta》2014,97(4):561-568
The one‐step cyclocondensation of substituted isoflavones (=3‐phenyl‐4H‐1‐benzopyran‐4‐ones) with cyanoacetohydrazide in the presence of KOH afforded a mixture of 1‐amino‐5,6‐diaryl‐3‐cyano‐1H‐2‐pyridin‐2‐ones and 6,7‐diaryl‐4‐cyano‐3‐hydroxy‐1H‐[1,2]diazepines. 相似文献
18.
Three title compounds 4a—4c have been synthesized by the cyclodehydration of 1’-benzylidine-4’-(3β-substituted-5α-cholestane-6-yl)thiosemicarbazones 2a—2c with thioglycolic acid followed by the treatment with cold conc. H2SO4 in dioxane. The compounds 2a—2c were prepared by condensation of 3β-substituted-5α-cholestan- 6-one-thiosemicarbazones 1a—1c with benzaldehyde. These thiosemicarbazones 1a—1c were obtained by the reaction of corresponding 3β-substituted-5α-cholestan-6-ones with thiosemicarbazide in the presence of few drops of conc. HCl in methanol. The structures of the products have been established on the basis of their elemental, analytical and spectral data. 相似文献
19.
Giuditta Bartalucci Charles Delroy Stuart Fisher Madeleine Helliwell Synnve Liaaen‐Jensen 《Acta Crystallographica. Section C, Structural Chemistry》2008,64(3):o128-o131
13‐cis‐β,β‐Carotene, C40H56, crystallizes with a complete molecule in the asymmetric unit, whereas 15‐cis‐β,β‐carotene, also C40H56, has twofold symmetry about an axis through the central bond of the polyene chain. The polyene methyl groups are arranged on one side of the polyene chains for each molecule and the 6‐s‐cisβ end groups, with the cyclohexene rings in half‐chair conformations, are twisted out of the planes of the polyene chains by angles ranging from 41.37 (17) to 52.2 (4)°. The molecules in each structure pack so that the arms of one occupy the cleft of the next, and there is significant π–π stacking of the almost‐parallel polyene chains of the 15‐cis isomer, which approach at distances of 3.319 (1)–3.591 (1) Å. 相似文献
20.
Reaction of 4H‐pyrimido[2,1‐b]benzothiazole‐2‐thiomethyl‐3‐cyano‐4‐one (1) with hydrazine hydrate/aryl hydrazine/heteryl hydrazine in the presence of anhydrous potassium carbonate and dimethyl formamide afforded 3‐amino‐4‐oxo‐(2H)/aryl/heteryl pyrazolo[3′,4′:4,5]pyrimido[2,1‐b]benzothiazoles in good yield. These pyrazole derivatives on diazotization followed by replacement with hydroxy, chloro, bromo, iodo and on reduction gave the corresponding 3‐substituted derivatives. 相似文献