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1.
《Journal of heterocyclic chemistry》2017,54(2):1604-1610
The starting compound 2‐hydrazinyl‐7‐(4‐methoxyphenyl)‐5‐oxo‐3,5‐dihydro[1,2,4]triazolo[1,5‐a ]pyridine‐6,8‐dicarbonitrile ( 5 ) was efficiently synthesized from 1,6‐diamino‐4‐(4‐methoxyphenyl)‐2‐oxo‐1,2‐dihydropyridine‐3,5‐dicarbonitrile ( 1 ). A novel series of polynuclear [1,2,4]triazolo[4′,3′:2,3][1,2,4]triazolo[1,5‐a ]pyridines 6 , 7 , 8 , 9 , 10 and pyrido[1′,2′:2,3][1,2,4]triazolo[5,1‐c ][1,2,4]triazines 11 , 12 , 13 , 14 , 15 have been synthesized. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity. 相似文献
2.
2a,4‐Disubstituted 2‐phenoxy‐2,2a,3,4‐tetrahydro‐1H‐azeto[2,1‐d][1,5]benzothiazepin‐1‐ones and 5‐benzoyl‐2‐phenoxy‐2a,3,4,5‐tetrahydro‐azeto[1, 2‐a][1,5]benzodiazepin‐1(2H)‐ones were synthesized in moderate to good yields by stereospecific Staudinger cycloaddition reactions of 2,4‐disubstituted 2,3‐dihydro‐1,5‐benzothiazepines and 1‐benzoyl‐2,3‐dihydro‐1H‐1,5‐benzodiazepines, respectively, with phenoxy acetyl chloride in the presence of triethylamine in anhydrous benzene. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:564–569, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10196 相似文献
3.
Reactions of 4,5‐Dihydro‐1,4‐Benzothiazepin‐3(2H)‐one 1,1‐Dioxide and 1,5‐Dihydro‐4,1‐Benzothiazepin‐2(3H)‐one 4,4‐Dioxide Derivatives with Vilsmeier Reagent and DMFDMA
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Taras M. Tarasiuk Tatyana A. Volovnenko Kirill S. Popov Volodymyr V. Medviediev Oleg V. Shishkin Yulian M. Volovenko 《Journal of heterocyclic chemistry》2014,51(3):755-759
The regioselectivity of the interaction between isomeric 4,5‐dihydro‐1,4‐benzothiazepin‐3(2H)‐one 1,1‐dioxide and 1,5‐dihydro‐4,1‐benzothiazepin‐2(3H)‐one 4,4‐dioxide derivatives with the Vilsmeier reagent and DMFDMA (N,N‐dimethylformamide dimethylacetal) has been investigated. The structures of synthesized compounds are confirmed by 1H, 13C NMR, elemental analysis, and X‐ray data. 相似文献
4.
《Magnetic resonance in chemistry : MRC》2002,40(12):797-799
Complete 1H and 13C NMR assignments for selected carotenoids from purple and green phototropic bacteria are reported for the first time. Assignments are made for the all‐E isomers of OH‐rhodopin ( 1 , 1,2,1′,2′‐tetrahydro‐ψ,ψ‐carotene‐1,1′‐diol), rhodovibrin ( 2 , 1′‐methoxy‐3′,4′‐didehydro‐1,2,1′,2′‐tetrahydro‐ψ,ψ‐carotene‐1‐ol), anhydrorhodovibrin ( 3 , 1‐methoxy‐3,4‐didehydro‐1,2‐dihydro‐ψ,ψ‐carotene), 2‐ketorhodovibrin ( 4 , 1′‐hydroxy‐1‐methoxy‐3,4,3′,4′‐tetradehydro‐1,2, 1′,2′‐tetrahydro‐ψ,ψ‐carotene‐2‐one) and chlorobactene ( 5 , ?,ψ‐carotene). Copyright © 2002 John Wiley & Sons, Ltd. 相似文献
5.
A stereoselective synthesis of new optically active 3‐(hydroxyalkyl)‐2,3‐dihydro‐1,5‐benzothiazepin‐4‐ones 4 and 7 was achieved by Michael‐like addition of o‐aminothiophenol to chiral α‐alkylidenelactons 1 and 5 followed by ring chain transformation of the resulting adducts 3 and 6. 相似文献
6.
Three new compounds, (5β,9β)‐guaia‐6,10(14)‐dien‐9‐ol (=rel‐(1R,3aS,5R,8aR)‐1,2,3,3a,4,5,6,8a‐octahydro‐1‐methyl‐4‐methylene‐7‐(1‐methylethyl)azulen‐5‐ol; 1 ), 6‐acetyl‐8‐methoxy‐2,3‐dimethylchromen‐4‐one (=6‐acetyl‐8‐methoxy‐2,3‐dimethyl‐4H‐1‐benzopyran‐4‐one; 2 ), and (2S)‐3′‐hydroxy‐5′,7‐dimethoxyflavanone (=(2S)‐2,3‐dihydro‐2‐(3‐hydroxy‐5‐methoxyphenyl)‐7‐methoxy‐4H‐1‐benzopyran‐4‐one; 3 ) were isolated from the roots and rhizomes of Ligularia macrophylla, together with seven known compounds. Their structures and configurations were elucidated by spectroscopic methods, including 2D‐NMR techniques. 相似文献
7.
Lingaiah Boddu Varakumar Potlapati N.J.P. Subhashini 《Journal of heterocyclic chemistry》2019,56(12):3197-3205
A series of novel isoindolone‐based macromolecules of medium‐sized heterocyclic rings, such as 7,8‐dihydro‐6H‐benzo[4,5][1,6,3]dioxazonino[2,3‐a]isoindol‐14(9aH)‐one derivatives ( 5a‐l ), were synthesized and its frame work incorporating with a triazole moiety on phenol, ie, 2‐(4‐((1‐(2‐methoxyphenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)isoindoline‐1,3‐dione ( 9a‐f ) and also a triazole moiety on carboxylic acid, ie, (1‐(2‐methoxyphenyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl 4‐(1,3‐dioxoisoindolin‐2‐yl)benzoate derivatives ( 13a‐e ) with various substitutions on aryl ring system have synthesized. All the synthesized compounds were characterized and confirmed with IR, 1H NMR, 13C NMR, and ESI mass spectral analysis. 相似文献
8.
Qi Zeng Xiang‐Rong Cheng Jiang‐Jiang Qin Bin Guan Rui‐Jie Chang Shi‐Kai Yan Hui‐Zi Jin Wei‐Dong Zhang 《Helvetica chimica acta》2012,95(4):606-612
Five new compounds, i.e., the three new norlignans metasequirins G–I ( 1 – 3 ) and the two new phenylpropanoids 7‐(3‐ethoxy‐5‐methoxyphenyl)propane‐7,8,9‐triol (=1‐(3‐ethoxy‐5‐methoxyphenyl)propane‐1,2,3‐triol; 4 ) and 7‐(3‐hydroxy‐5‐methoxyphenyl)propane‐7,8,9‐triol (=1‐(3‐hydroxy‐5‐methoxy‐phenyl)propane‐1,2,3‐triol; 5 ), were isolated from the branches and stems of Metasequoia glyptostroboides Hu et Cheng . Their structures were elucidated by physical, chemical, and spectroscopic methods, including 1D‐ and 2D‐NMR and HR‐ESI‐MS. The cytotoxicites of the five compounds were tested against A549 and Colo 205 cell lines by the MTT method. 相似文献
9.
Yu‐Chang Chen Ming‐Jen Cheng Shoiw‐Ju Lee AjayKumar Dixit Tsutomu Ishikawa Ian‐Lih Tsai Ih‐Sheng Chen 《Helvetica chimica acta》2004,87(11):2805-2811
Four new coumarinolignans, antidesmanin A (=7‐(1,1‐dimethylallyl)‐2,3‐dihydro‐3‐(4‐hydroxy‐3,5‐dimethoxyphenyl)‐10‐methoxy‐2‐methyl‐6H‐1,4,5‐trioxaphenanthren‐6‐one; 1 ), antidesmanin B (=3,7‐bis(1,1‐dimethylallyl)‐2,3‐dihydro‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐10‐methoxy‐6H‐1,4,5‐trioxaphenanthren‐6‐one; 2 ), antidesmanin C (=2,7‐bis‐(1,1‐dimethylallyl)‐2,3‐dihydro‐3‐(4‐hydroxy‐3‐methoxyphenyl)‐10‐methoxy‐6H‐1,4,5‐trioxaphenanthren‐6‐one; 3 ) and antidesmanin D (=2‐(3,4‐dihydroxyphenyl)‐3,7‐bis(1,1‐dimethylallyl)‐2,3‐dihydroxy‐10‐methoxy‐6H‐1,4,5‐trioxaphenanthren‐6‐one or 3‐(3,4‐dihydroxyphenyl)‐2,7‐bis(1,1‐dimethylallyl)‐2,3‐dihydro‐10‐methoxy‐6H‐1,4,5‐trioxaphenanthren‐6‐one; 4 ) have been isolated from the root of the Formosan Antidesma pentandrum var. barbatum. The structures of these new compounds were elucidated by spectroscopic data. Compounds 1 – 3 exhibited marginal cytotoxicity against MCF‐7 (breast) and SF‐268 (CNS) cancer cell lines in vitro. 相似文献
10.
Victoria V. Lipson Nataliya V. Svetlichnaya Victoria V. Borodina Maria G. Shirobokova Sergey M. Desenko Vladimir I. Musatov Svetlana V. Shishkina Oleg V. Shishkin Roman I. Zubatyuk 《Journal of heterocyclic chemistry》2012,49(5):1019-1025
Formylation of 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine 1a using Vilsmeier–Haack conditions yields 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidin‐6‐ylcarbaldehyde 3a . 5,7‐Diaryl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidines 1b , 1c in this reaction apart from formylation undergo recyclization into 5‐aryl‐1,2,4‐triazolo[1,5‐a]pyrimidin‐6‐ylmethane derivatives 4b , 4c , 5b , 5c , and 6 . The structure of the synthesized compounds was determined on the basis of NMR, IR, and MS spectroscopic data and confirmed by the X‐ray analysis of the 6‐(ethoxy‐phenyl‐methyl)‐5‐phenyl‐[1,2,4]triazolo[1,5‐a]pyrimidine 6 , 5‐phenyl‐6‐(1‐phenyl‐vinyl)‐[1,2,4]triazolo[1,5‐a]pyrimidine 11 , and 7‐phenyl‐6‐(1‐phenyl‐vinyl)‐[1,2,4]triazolo[4,3‐a]pyrimidine 12 . 相似文献
11.
Chunping Xie Paul M. Lahti 《Journal of polymer science. Part A, Polymer chemistry》1999,37(6):779-788
Carbon—carbon bond‐forming polymerization of 2‐bromo‐3‐(3′,5′‐di‐t‐butyl‐4′‐methoxyphenyl)‐thiophene yields poly[3‐(3′,5′‐di‐t‐butyl‐4′‐methoxyphenyl)‐2,5‐thienylene] with regiospecific connectivity and a degree of polymerization of about six. Lewis‐acid‐moderated‐cleavage of the methoxy groups on the pendant phenyl group yield the corresponding polyphenolic polymer, which is oxidized under solution conditions to yield the title polyradical. Poly[3‐(3′,5′‐di‐t‐butyl‐4′‐oxyphenyl)‐2,5‐thienylene] exhibits a strong, persistent electron spin resonance spectrum and a UV–visible spectrum consistent with formation of the pendant phenoxyl spin‐bearing units. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 779–788, 1999 相似文献
12.
Gajendra Singh Anoop K. Sharma Neeraj Kumar L. Prakash 《Research on Chemical Intermediates》2000,26(5):445-453
(±)cis-2-(4-methoxyphenyl)-3-hydroxy/methoxy-6-methoxy/8-methoxy-2,3-dihydro-1,5-benzothiazepin-4-[5H/5-chloroacetyl/5-(4′-methylpiperazino-1′)acetyl]-ones
and nucleosides viz; (±)cis-2-(4-methoxyphenyl)-3,6-dimethoxy-2,3-dihydro-1,5-benzothiazepin-4-[5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)]-one and (±)cis-2-(4-methoxyphenyl)-3,8-dimethoxy-2,3-dihydro-1,5-benzothiazepin-4-[5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)]-one have been
synthesized by the condensation of substituted-2-aminobenzenethiols with methyl (±)trans-3-(4-methoxyphenyl)glycidate in xylene and by stirring the 3-methoxy derivative of 1,5-benzothiazepin-4(5H)-ones with sugar
namely β-D-ribofuranosyl-1-acetate-2,3,5-tribenzoate at 155–160 °C in vacuo for 10 hours, respectively.
The synthesized compounds have been characterized by the elemental analyses and spectral data and screened for their antimicrobial
activity. 相似文献
13.
Qing‐An Zheng Hai‐Zhou Li Ying‐Jun Zhang Chong‐Ren Yang 《Helvetica chimica acta》2004,87(5):1167-1171
Chemical investigation of the red herbal resin of Dracaena cochinchinensis resulted in the isolation of three new configurationally isomeric flavonoids: 6,4′‐dihydroxy‐7‐methoxy‐8‐methylflavane (=3,4‐dihydro‐2‐(4‐hydroxyphenyl)‐7‐methoxy‐8‐methyl‐2H‐[1]benzopyran‐6‐ol; 1 ), 5,4′‐dihydroxy‐7‐methoxy‐6‐methylflavane (=3,4‐dihydro‐2‐(4‐hydroxyphenyl)‐7‐methoxy‐6‐methyl‐2H‐[1]benzopyran‐5‐ol; 2 ), and 7,4′‐dihydroxy‐5‐ methoxyhomoisoflavane (=3,4‐dihydro‐3‐[(4‐hydroxyphenyl)methyl]‐5‐methoxy‐2H‐[1]benzopyran‐7‐ol; 3 ). Their structures were identified by means of detailed spectral analysis. In addition, thirteen known compounds were isolated from D. cochinchinensis: 7‐hydroxy‐4′‐methoxyflavane ( 4 ), 2,4,6‐trimethoxy‐4′‐hydroxydihydrochalcone ( 5 ), 2,4‐dimethoxy‐4′‐hydroxydihydrochalcone ( 6 ), 7,8‐(methylenedioxy)‐4′‐hydroxyhomoisoflavane ( 7 ), 4′,7‐dihydroxy‐8‐methylflavane ( 8 ), 2,6‐dimethoxy‐4,4′‐dihydroxydihydrochalcone ( 9 ), 2‐methoxy‐4,4′‐dihydroxydihydrochalcone ( 10 ), 7‐methoxy‐6,4′‐dihydroxyhomoisoflavane ( 11 ), 2‐methoxy‐4,4′‐dihydroxychalcone ( 12 ), 4′,7‐dihydroxyflavane ( 13 ), 7,4′‐dihydroxyhomoisoflavane ( 14 ), 7,4′‐dihydroxyhomoisoflavone ( 15 ), and 7,4′‐dihydroxyflavone ( 16 ). Compounds 7, 8, 9, 14 , and 15 have been isolated for the first time from this type of herbal source. 相似文献
14.
Three new neolignans, named 1‐deoxycarinatone ( 1 ), isodihydrocarinatidin ( 2 ), and isolicarin A ( 3 ), together with the known neolignan (+)‐dehydrodiisoeugenol ( 4 ), were isolated from mace (the aril of Myristica fragrans Houtt .). Their structures were elucidated as 2‐[(1S)‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐1‐methylethyl]‐6‐methoxy‐4‐(prop‐2‐enyl)phenol ( 1 ), 4‐[(2R,3R)‐2,3‐dihydro‐7‐methoxy‐3‐methyl‐5‐(prop‐2‐enyl)benzofuran‐2‐yl]‐2‐methoxyphenol ( 2 ), and 4‐{(2S,3R)‐2,3‐dihydro‐7‐methoxy‐3‐methyl‐5‐[(1E)‐prop‐1‐enyl]benzofuran‐2‐yl}‐2‐methoxyphenol ( 3 ) on the basis of spectroscopic data. 相似文献
15.
An efficient method for the extraction of the carotenoids from Curtobacterium flaccumfaciens pvar poinsettiae was developed. The glucosides of C.p. 450 (=(all‐E,2R,2′R)‐2‐[4‐(β‐D ‐glucopyranosyloxy)‐3‐methylbut‐2‐enyl]‐2′‐(4‐hydroxy‐3‐methylbut‐2‐enyl)‐β, β‐carotene; 4 ) and of C.p. 473 (=(all‐E,2R,2′S)‐2‐[4‐(β‐D ‐glucopyranosyloxy)‐3‐methylbut‐2‐enyl]‐2′‐(3‐methylbut‐2‐enyl)‐3′,4′‐didehydro‐1′,2′‐dihydro‐β,ψ‐caroten‐1′‐ol; 5 ) were isolated for the first time. In addition, the hitherto unknown 3′,4′‐dihydro derivative of C.p. 450, called C.p. 460 (=(all‐E,2R,2′R)‐2‐(4‐hydroxy‐3‐methylbut‐2‐enyl)‐2′‐(3‐methylbut‐2‐enyl)‐1′,2′‐dihydro‐β,ψ‐caroten‐1′‐ol; 6 ), was identified. The structures were established by UV/VIS, CD, 1H‐ and 13C‐NMR, and mass spectra. 相似文献
16.
Nisar Ullah Prinz Sonja Ernst Haslinger Wagar Ahmed Mohammed Arfan Abdul Malik 《Helvetica chimica acta》2001,84(1):157-162
Three new natural products, a lignoid glycoside 1 and two dimeric phenylpropanoids 2 and 3 , along with two known lignans 4 and 5 , were isolated from the BuOH‐ and CHCl3‐soluble fractions of the whole plant of Daphne oleoides (Thymelaeaceae). The structures of the new compounds were established by spectroscopic techniques, including 2D NMR, as 4‐(β‐D ‐glucopyranosyloxy)‐9′‐hydroxy‐3,3′,4′‐trimethoxy‐7′,9‐epoxylignan ( 1 ), (1R,2S,5R,6R)‐6‐(3‐ethyl‐4‐hydroxy‐5‐methoxyphenyl)‐2‐(4‐hydroxy‐3,5‐dimethoxyphenyl)‐3,7‐dioxabicyclo[3.3.0]octane ( 2 ) and (1R,2S,5R,6S)‐2,6‐bis(3‐ethyl‐4‐hydroxy‐5‐methoxyphenyl)‐3,7‐dioxabicyclo[3.3.0]octane ( 3 ). The other lignans were identified as (+)‐pinoresinol O‐(β‐D ‐glucopyranoside) ( 4 ) and (+)‐medioresinol ( 5 ). 相似文献
17.
Hyuk Yoon Seunghyun Ahn Doseok Hwang Geunhyeong Jo Dong Woon Kim Sang Ho Kim Dongsoo Koh Yoongho Lim 《Magnetic resonance in chemistry : MRC》2012,50(11):759-764
Several types of chalcones containing 2H‐chromen group were synthesized. Claisen–Schmidt condensation of 2H‐chromen‐3‐carbaldehydes (I) with methoxy substituted acetophenones afforded (E)‐3‐(2H‐chromen‐3‐yl)‐1‐(methoxyphenyl)prop‐2‐en‐1‐ones (chromenylchalcones, 1–7). Other types of chromenylchalcone, (E)‐1‐(6‐methoxy‐2H‐chromen‐3‐yl)‐3‐(methoxyphenyl)prop‐2‐en‐1‐ones (8–13) were also obtained between reaction of methoxy substituted benzaldehydes and 1‐(6‐methoxy‐2H‐chromen‐3‐yl)ethanone (II). Dichromenylchalcones (14–16) were also synthesized through the same reaction between aldehydes (I) and ketone (II). Their complete 1H‐NMR and 13C‐NMR assignments are reported here and more polysubstituted chromenylchalcones synthesized or isolated from the natural sources in the future can be identified on the basis of the NMR data reported here. Copyright © 2012 John Wiley & Sons, Ltd. 相似文献
18.
Phenylalanine and histidine ammonia lyases (PAL and HAL) catalyze the reversible conversion of α‐amino acids to the corresponding acrylic acids by elimination of ammonia. The prosthetic group 3,5‐dihydro‐5‐methylidene‐4H‐imidazol‐4‐one (MIO) at the active site of both enzymes supposedly undergoes an electrophilic attack at the aromatic nucleus in the first step of the mechanism of action. Since no chemical analogy existed for such an electrophile‐assisted elimination, we synthesized model compounds, some portion of which mimicked the essentials of the substrate phenylalanine and another portion the electrophilic Michael acceptor in a sterically appropriate distance. The first model, (±)‐rel‐(1R,2S,3S)‐3‐[1‐methylidene‐2‐oxo‐2‐(pyrrolidin‐1‐yl)ethyl]‐2‐phenylcyclohexanamine ( 7 ) did not react under Friedel‐Crafts conditions in the expected way (Scheme 2). The second model compound (±)‐2‐rel‐(1R,2S,3S)‐3‐(dimethylamino)‐2‐(3‐methoxyphenyl)cyclohexyl]prop‐2‐enal ( 12 ) with a more nucleophilic methoxyphenyl and a more electrophilic α,β‐unsaturated carbonyl moiety, underwent an intramolecular Friedel‐Crafts‐type substitution, but no elimination of the dimethylamino group (Scheme 4). The third model compound, (±)‐γ‐[(dimethylamino)methyl]‐3‐methoxy‐2,4,6‐trimethyl‐α‐methylidenebenzenebutanal ( 25 ) eliminated dimethylamine upon treatment with Lewis acids and subsequent hydrolysis of the intermediate (Scheme 6). When the 3‐methoxy‐2,4,6‐trimethylphenyl moiety of 25 was replaced by the 2,4,6‐trimethyl‐3‐nitrophenyl group, no elimination product could be observed (Scheme 7). 相似文献
19.
Yun‐Mei Bi Xu‐Bin Bi Qian‐Rong Zhao Yuan‐Teng Chen Jin‐Lun Xie 《Helvetica chimica acta》2004,87(11):2890-2895
Four novel dihydroisocoumarin (=3,4‐dihydro‐1H‐2‐benzopyran‐1‐one) glucosides were isolated from a culture broth of a strain of the fungus Cephalosporium sp. AL031. Their structures were elucidated as (2E,4E)‐5‐[(3S)‐5‐acetyl‐8‐(β‐D ‐glucopyranosyloxy)‐3,4‐dihydro‐6‐hydroxy‐1‐oxo‐1H‐2‐benzopyran‐3‐yl]penta‐2,4‐dienal ( 1 ), (2E,4E)‐5‐[(3S)‐5‐acetyl‐8‐(β‐D ‐glucopyranosyloxy)‐3,4‐dihydro‐6‐methoxy‐1‐oxo‐1H‐2‐benzopyran‐3‐yl]penta‐2,4‐dienal ( 2 ), (3S)‐8‐(β‐D ‐glucopyranosyloxy)‐3‐[(1E,3E,5E)‐hepta‐1,3,5‐trienyl]‐3,4‐dihydro‐6‐hydroxy‐5‐methyl‐1H‐2‐benzopyran‐1‐one ( 3 ), and (3S)‐8‐[(6‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]‐3‐[(1E,3E,5E)‐hepta‐1,3,5‐trienyl]‐3,4‐dihydro‐6‐methoxy‐5‐methyl‐1H‐2‐benzopyran‐1‐one ( 4 ) by spectroscopic methods, including 2D‐NMR techniques and chemical methods. 相似文献