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1.
《Magnetic resonance in chemistry : MRC》2003,41(4):296-300
The oxoisoaporphines 2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one, 2,3‐dihydro‐5‐methoxy‐7H‐dibenzo [de,h] quinolin‐7‐one, 5‐methoxy‐6‐hydroxy‐2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one, 5,6‐dimethoxy‐2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one and 5,6‐methylenedi‐oxy‐2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one were prepared by cyclization of phenylethylaminophthalides with polyphosphoric acid or by treating 1‐(2‐carboxyphenyl)‐3,4‐dihydroisoquinoline hydrochloride with sulfuric acid at 0 °C. The structures were confirmed and 1H and 13C NMR spectra were completely assigned using a combination of one‐ and two‐dimensional NMR techniques. Copyright © 2003 John Wiley & Sons, Ltd. 相似文献
2.
Jean Fotie Hilaire V. Kemami Wangun Katelyn Dreux Thomas Sommerfeld Jacob Pittman 《Magnetic resonance in chemistry : MRC》2012,50(1):68-73
Because of their extreme instability, it is generally difficult to synthesize and fully characterize open chain peroxides, also known as peroxols. In our attempt to investigate the mechanism of the Skraup–Doebner–Von Miller quinoline synthesis, we were able to obtain an unusual open chain peroxy‐quinoline, namely, 4‐(8‐ethoxy‐2,3‐dihydro‐1H‐cyclopenta[c]quinolin‐4‐yl)butane‐1‐peroxol (1), and its alcohol counterpart, namely 4‐(8‐ethoxy‐2,3‐dihydro‐1H‐cyclopenta[c]quinolin‐4‐yl)butan‐1‐ol (2) obtained as a side product during the same reaction. Although structurally similar, these two compounds appeared to display some very distinct physical and spectroscopic characteristics. This work reports detailed NMR studies and full 1H and 13 C NMR assignments for these two compounds. These assignments are based upon the analysis of the NMR spectra of these compounds including 1H, 13 C, COSY, gHSQC and gHMBC. The effect of the peroxide functional group on the chemical shift of neighboring carbons and protons was also investigated by comparing the NMR data of these two compounds. Furthermore, the effects of potential hydrogen bondings in 1, 2, and possible 1–1 dimer, 2–2 dimer and in prototypical model systems, as well as the stability of these compounds, were investigated computationally. The computed dissociation energies and NMR data support the interpretation of the experimental data. Copyright © 2012 John Wiley & Sons, Ltd. 相似文献
3.
Eduardo Sobarzo‐Sánchez Eugenio Uriarte Lourdes Santana Ricardo A. Tapia Paulo Pérez Lourido 《Helvetica chimica acta》2010,93(7):1385-1394
2,3‐Dihydro‐6‐hydroxy‐5‐methoxy‐7H‐dibenzo[de,h]quinolin‐7‐one, 6‐hydroxy‐5‐methoxy‐7H‐dibenzo[de,h]quinolin‐7‐one, and 2‐(6,7‐dimethoxy‐3,4‐dihydroisoquinolin‐1‐yl)benzyl benzoate, easily available by a Bischler–Napieralski cyclization, were used as starting materials to afford 6‐oxoisoaporphine and 2,3‐dimethoxy‐5,6,8,12b‐tetrahydroisoindolo[1,2‐a]isoquinoline as the main products. However, the catalytic hydrogenation of the benzyl benzoate derivative afforded, under mild conditions, 1,2,3,4‐tetrahydro‐6,7‐dimethoxy‐1‐(2‐methylphenyl)isoquinoline. 相似文献
4.
Sobarzo-Sánchez E De la Fuente J Castedo L 《Magnetic resonance in chemistry : MRC》2005,43(12):1080-1083
The new oxoisoaporphines 7H-dibenzo[de,h]quinolin-7-one, 5-methoxy-7H-dibenzo[de,h]quinolin-7-one, 5-methoxy-6-hydroxy-7H-dibenzo[de,h]quinolin-7-one, 5-hydroxy-7H-dibenzo[de,h]quinolin-7-one and 5-methoxy-6H-dibenzo[de,h]quinolin-6-one were prepared either by oxidation of their 2,3-dihydro derivatives or by heating (2'-(3,4-dihydro-6,7-dimethoxyisoquinolin-1'-yl)phenyl)methylbenzoate with an acetic acid/sulfuric acid mixture at 100 degrees C. The structures were confirmed and 1H and 13C NMR spectra were completely assigned using two-dimensional NMR techniques. 相似文献
5.
Carlos M. Sanabría Alirio Palma Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2014,70(3):332-337
In the structure of (6R*,11R*)‐5‐acetyl‐11‐ethyl‐6,11‐dihydro‐5H‐dibenzo[b,e]azepine‐6‐carboxylic acid, C19H19NO3, (I), the molecules are linked into sheets by a combination of O—H...O and C—H...O hydrogen bonds; in the structure of the monomethyl analogue (6RS,11SR)‐5‐acetyl‐11‐ethyl‐2‐methyl‐6,11‐dihydro‐5H‐dibenzo[b,e]azepine‐6‐carboxylic acid, C20H21NO3, (II), the molecules are linked into simple C(7) chains by O—H...O hydrogen bonds; and in the structure of the dimethyl analogue (6RS,11SR)‐5‐acetyl‐11‐ethyl‐1,3‐dimethyl‐6,11‐dihydro‐5H‐dibenzo[b,e]azepine‐6‐carboxylic acid, C21H23NO3, (III), a combination of O—H...O, C—H...O and C—H...π(arene) hydrogen bonds links the molecules into a three‐dimensional framework structure. None of these structures exhibits the R22(8) dimer motif characteristic of simple carboxylic acids. 相似文献
6.
Raphaël Labruère Philippe Helissey Stéphanie Desbène‐Finck Sylviane Giorgi‐Renault 《Helvetica chimica acta》2013,96(5):919-923
In the context of our aim of discovering new antitumor drugs among synthetic γ‐lactone‐ and γ‐lactam‐fused 1‐methylquinolin‐4(1H)‐ones, we developed a rapid access to 5‐methyl‐1,3‐dioxolo[4,5‐g]furo[3,4‐b]quinoline‐8,9(5H,6H)‐dione ( 9 ) exploiting the γ‐lactone‐fused chloroquinoline 10 previously synthesized in our laboratory (Scheme 1). We also elaborated efficient synthetic methods allowing for a rapid access to two nonclassical bioisosteres of 9 , i.e., a deoxy and a carba analogue. The deoxy analogue 11 was prepared in two steps from the γ‐lactone‐fused quinoline 13 which was also the synthetic precursor of 10 (Scheme 1). The carba analogue 6,9‐dihydro‐5‐methyl‐9‐methylene‐1,3‐dioxolo[4,5‐g]furo[3,4‐b]quinolin‐8(5H)‐one ( 12 ) was easily prepared by HCl elimination from the 9‐(chloromethyl)dioxolofuroquinoline 15 , which was obtained via a three‐component one‐pot reaction from N‐methyl‐3,4‐(methylenedioxy)aniline (=N‐methyl‐1,3‐benzodioxol‐5‐amine; 16 ), commercially available chloroacetaldehyde, and tetronic acid ( 17 ) (Scheme 2). 相似文献
7.
A series of new pyrazolo[4,3‐f]quinolin‐7‐one derivatives were synthesized by multi‐component reactions of equimolar amount of aromatic aldehydes with 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione and 1H‐indazol‐5‐amine in ethylene glycol without catalyst under microwave irradiation. This one‐pot protocol has the advantage of good yields, simple workup procedure and shorter reaction time. 相似文献
8.
Braulio Insuasty Diana Becerra Jairo Quiroga Rodrigo Abonia Manuel Nogueras Justo Cobo 《Journal of heterocyclic chemistry》2013,50(3):506-512
The 5,6,7,8,9,10‐hexahydro‐2‐methylthiopyrimido[4,5‐b]quinolines 4a , 4b , 4c , 4d , 5a , 5b , 5c , 5d and their oxidized forms 6a , 6b , 6c , 6d , 7a , 7b , 7c , 7d were obtained from the reaction of 6‐amino‐2‐(methylthio)pyrimidin‐4(3H)‐one 2 or 6‐amino‐3‐methyl‐2‐(methylthio)pyrimidin‐4(3H)‐one 3 and α,β‐unsaturated ketones 1a , 1b , 1c , 1d using BF3.OEt2 as catalyst and p‐chloranil as oxidizing agent. Some of the new compounds were evaluated in the US National Cancer Institute (NCI), where compound 5a presented remarkable activity against 46 cancer cell lines, with the most important GI50 values ranging from 0.72 to 18.4 μM from in vitro assays. 相似文献
9.
Yue Sun Zhongfei Gao Chunhua Wang Guige Hou 《Acta Crystallographica. Section C, Structural Chemistry》2019,75(8):1157-1165
Two fluorine‐substituted 1,4,5,6‐tetrahydrobenzo[h]quinazolin‐2‐amine (BQA) derivatives, namely 2‐amino‐4‐(2‐fluorophenyl)‐9‐methoxy‐1,4,5,6‐tetrahydrobenzo[h]quinazolin‐3‐ium chloride, ( 8 ), and 2‐amino‐4‐(4‐fluorophenyl)‐9‐methoxy‐1,4,5,6‐tetrahydrobenzo[h]quinazolin‐3‐ium chloride, ( 9 ), both C19H19FN3O+·Cl?, were generated by Michael addition reactions between guanidine hydrochloride and the α,β‐unsaturated ketones (E)‐2‐(2‐fluorobenzylidene)‐7‐methoxy‐3,4‐dihydronaphthalen‐1(2H)‐one, C18H15FO2, ( 6 ), and (E)‐2‐(4‐fluorobenzylidene)‐7‐methoxy‐3,4‐dihydronaphthalen‐1(2H)‐one, ( 7 ). Because both sides of α,β‐unsaturated ketones ( 6 ) or ( 7 ) can be attacked by guanidine, we obtained a pair of isomers in ( 8 ) and ( 9 ). Single‐crystal X‐ray diffraction indicates that each isomer has a chiral C atom and both ( 8 ) and ( 9 ) crystallize in the achiral space group P21/c. The chloride ion, as a hydrogen‐bond acceptor, plays an important role in the formation of multiple hydrogen bonds. Thus, adjacent molecules are connected through intermolecular hydrogen bonds to generate a banded structure. Furthermore, these bands are linked into an interesting 3D network via hydrogen bonds and π–π interactions. Fortunately, the solubilities of ( 8 ) and ( 9 ) were distinctly improved and can exceed 50 mg ml?1 in water or PBS buffer system (pH 7.4) at room temperature. In addition, the results of an investigation of anti‐inflammatory activity show that ( 8 ) and ( 9 ), with o‐ and p‐fluoro substituents, respectively, display more potential for inhibitory effects on LPS‐induced NO secretion than starting ketones ( 6 ) and ( 7 ). 相似文献
10.
《Magnetic resonance in chemistry : MRC》2003,41(4):301-303
4‐Methyl‐6,8‐dihydroxy‐7H‐benz[de]anthracen‐7‐one was isolated from the sap of Aloe by column chromatography. Its 1H and 13C NMR spectra were completely assigned by utilizing two‐dimensional 1H‐detected heteronuclear one‐bond (HMQC) and multiple‐bond (HMBC) chemical shift correlation experiments together with 1H–1H COSY and DEPT techniques. These techniques were also valuable in assigning the protons and carbons of those benzanthrone compounds which were previously incompletely reported because of the overlap of proton signals. The molecular structure was elucidated by 2D NMR analysis. The spectral properties (MS, IR and UV) are also presented. Copyright © 2003 John Wiley & Sons, Ltd. 相似文献
11.
Jing‐Hua Yang Liang Li Yun‐Song Wang Jing‐Feng Zhao Hong‐Bin Zhang Shi‐De Luo 《Helvetica chimica acta》2005,88(9):2523-2526
Chemical examination of the BuOH extract of the leaves and twigs of Litsea glutinosa collected from Xishuangbanna resulted in the isolation of two new aporphine alkaloids, namely litseglutine A ( 1 ) and B ( 2 ), along with two known aporphine alkaloids, boldine ( 3 ) and laurolitsine ( 4 ). The structures of the new alkaloids have been elucidated on the basis of spectra analysis as 6‐demethyl‐9‐methoxy‐1,2‐(methylenedioxy)aporphin‐10‐ol (=6,7,7a,8‐tetrahydro‐10‐methoxy‐5H‐benzo[g]‐1,3‐benzodioxolo[6,5,4‐de]quinolin‐11‐ol; 1 ) and 1,10,11‐trimethoxyaporphin‐2‐ol (=5,6,6a,7‐tetrahydro‐1,10,11‐trimethoxy‐6‐methyl‐4H‐dibenzo[de,g]quinolin‐2‐ol; 2 ). 相似文献
12.
Dihydrobenzo[h]coumarins (5a–7a) and their 4‐methyl analogs (5b–7b) were synthesized from 1‐naphthol via two different synthetic routes. One pathway is the direct condensation of 5,8‐dihydro‐1‐naphthol (9) with malic acid or ethyl acetoacetate, affording 7,10‐dihydrobenzo[h]coumarins 7a and 7b, respectively. The other is through the oxidation of 7,8,9,10‐tetrahydrobenzo[h] coumarins (15a–b), followed by the reduction of the carbonyl group and dehydration of hydroxyl group, giving 7,8-dihydrobenzo[h]coumarins (5a, b) and 9,10-dihydrobenzo[h]coumarins (6a, b). The regio selectivities for the oxidation reactions of 15a, b were rationalized on the basis of quantum chemical calculations and further confirmed by the X‐ray crystallographic analysis of the derivatives of oxidation products. 相似文献
13.
Vladimír Mrkvička Antonín Lyčka Robert Vícha Antonín Klásek 《Helvetica chimica acta》2011,94(1):78-91
3‐Hydroxyquinoline‐2,4‐diones 1 react with isocyanates to give novel 1,2,3,4‐tetrahydro‐2,4‐dioxoquinolin‐3‐yl (alkyl/aryl)carbamates 2 and/or 1,9b‐dihydro‐9b‐hydroxyoxazolo[5,4‐c]quinoline‐2,4(3aH,5H)‐diones 3 . Both of these compounds are converted, by boiling in cyclohexylbenzene solution in the presence of Ph3P or 4‐(dimethylamino)pyridine, to give 3‐(acyloxy)‐1,3‐dihydro‐2H‐indol‐2‐ones 8 . All compounds were characterized by IR, and 1H‐ and 13C‐NMR spectroscopy, as well as by EI mass spectrometry. 相似文献
14.
Ali Ramazani Nader Noshiranzadeh Alieh Ghamkhari Katarzyna Ślepokura Tadeusz Lis 《Helvetica chimica acta》2008,91(12):2252-2261
Highly reactive 1 : 1 intermediates were produced in the reaction of Ph3P and dialkyl acetylenedicarboxylates (=dialkyl but‐2‐ynedioates). Protonation of these intermediates by alcohols (2,2,2‐trichloroethanol, propargyl alcohol (=prop‐2‐yn‐1‐ol), MeOH, benzyl alcohol, and allyl alcohol (=prop‐2‐en‐1‐ol) led to vinyltriphenylphosphonium salts 4 , which underwent a Michael addition reaction with the conjugate base to produce the corresponding stabilized phosphonium ylides 5 (Scheme). Wittig reaction of the stabilized phosphonium ylides with ninhydrin ( 6 ) led to the corresponding densely functionalized 2H‐indeno[2,1‐b]furans 10 in fairly good yields (Table 1). The structures of the final products were confirmed by IR, 1H‐ and 13C‐NMR spectroscopy, and mass spectrometry. The configuration of dimethyl 8,8a‐dihydro‐8‐oxo‐8a‐(2,2,2‐trichloroethoxy)‐2H‐indeno[2,1‐b]furan‐2,3‐dicarboxylate ( 10a ) was established by a single‐crystal X‐ray structure determination, establishing that the one‐pot multicomponent condensation reaction was completely diastereoselective. 相似文献
15.
A new class of [1,2,4]oxadiazolo[4,5‐a]thiazolo[2,3‐b]pyrimidin‐9(10H)‐one was prepared in moderate yields by the reaction of nitrile oxide with 2‐arylmethylidene‐6,7‐dihydro‐5H‐thiazolo[3,2‐a]pyrimidin‐3‐one. The reaction site of dipolarphile is the C?N of thiazolo[3,2‐a]pyrimidin‐3‐one rather than the expected C?C of arylmethylidene. The structures of the products were characterized thoroughly by IR, elemental analysis, MS, and NMR analysis. 相似文献
16.
An Efficient Synthesis of Spiro‐oxindole Derivatives by Three‐Component Reactions in Water
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An efficient synthesis of (3S)‐1,1′,2,2′,3′,4′,6′,7′‐octahydro‐9′‐nitro‐2,6′‐dioxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carbonitrile is achieved via a three‐component reaction of isatin, ethyl cyanoacetate, and 1,2,3,4,5,6‐hexahydro‐2‐(nitromethylidene)pyrimidine. The present method does not involve any hazardous organic solvents or catalysts. Also the synthesis of ethyl 6′‐amino‐1,1′,2,2′,3′,4′‐hexahydro‐9′‐nitro‐2‐oxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carboxylates in high yields, at reflux, using a catalytic amount of piperidine, is described. The structures were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS data) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2). 相似文献
17.
Lianbao Ye Yuanxin Tian Zhonghuang Li Jiajie Zhang Shuguang Wu 《Helvetica chimica acta》2012,95(2):320-326
Since deregulation of the tyrosine‐kinase receptor c‐Met is implicated in several human cancers and is an attractive target for small‐molecule‐drug discovery, we report herein the synthesis of 2,3,4,5‐tetrahydro‐8‐[1‐(quinolin‐6‐ylmethyl)‐1H‐1,2,3‐triazolo[4,5‐b]pyrazin‐6‐yl]‐1H‐pyrido[4,3‐b]indoles 4a – 4c and 2,3,4,5‐tetrahydro‐8‐[3‐(quinolin‐6‐ylmethyl)‐1,2,4‐triazolo[4,3‐b]pyridazin‐6‐yl]‐1H‐pyrido[4,3‐b]indoles 5a – 5c . These indole derivatives demonstrated inhibition of c‐Met kinase activity. Concurrently, five key intermediates were synthesized. These compounds could be prepared in good yields. 相似文献
18.
A novel procedure for the synthesis of 14‐aryl‐14H‐dibenzo[a,j]xanthenes through one‐pot condensation of naphthalen‐2‐ol with arenecarbaldehydes in the presence of N‐bromosuccinimide (NBS) as catalyst under solvent‐free conditions is described. 相似文献
19.
Jiann‐Kuan Luo Maria P. Cabal Ronald F. Federspiel Raymond N. Castle 《Journal of heterocyclic chemistry》2000,37(4):997-1001
Photocyclization of 3‐chloro‐N‐(9‐phenanthryl)benzo[b]‐thiophene‐2‐carboxamide ( 3 ) and 3‐chloro‐N‐(9‐phenanthryl)‐naphtho[1,2‐b]thiophene‐2‐carboxamide ( 10 ) yielded dibenzo[f,h]benzothieno[2,3‐c]‐quinolin‐10(9H)‐one ( 4 ) and dibenzo[f,h]naphtho[2′,1′:4,5]thieno[2,3‐c]quinolin‐10(9H)‐one ( 11 ), respectively. Further elaboration of the lactams provided three novel unsubstituted new ring systems. 相似文献
20.
《Magnetic resonance in chemistry : MRC》2003,41(9):718-720
A novel dihydroisocoumarin, 3,4‐dihydro‐6,8‐dihydroxy‐3‐(2′‐acetyl‐3′‐hydroxy‐5′‐methoxy)methyl‐1H‐[2]benzopyran‐1‐one, was isolated from the chloroform extract of the sap of the traditional herb Aloe vera. Its structure was determined by high‐resolution negative fast atom bombardment mass spectrometry (MS), 2D NMR spectroscopy and x‐ray crystallography. The molecular structure was elucidated by 2D NMR analysis. The complete assignment of the 1H and 13C NMR spectra of this compound was performed by using 1H detected one‐bond heteronuclear multiple quantum correlation (HMQC) and long‐range (two and three bonds) heteronuclear multiple quantum bond correlation (HMBC) experiments. Detailed analyses of the one‐ and two‐dimensional NMR techniques are presented in additional to the spectral properties (MS, IR and UV). Copyright © 2003 John Wiley & Sons, Ltd. 相似文献