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1.
István Szatmári 《Tetrahedron letters》2006,47(23):3881-3883
As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereoselective processes, resulting in the cis isomers as the main or the only products. 相似文献
2.
V. A. Osyanin E. A. Ivleva D. V. Osipov Yu. N. Klimochkin 《Chemistry of Heterocyclic Compounds》2011,47(7):845-850
Products of heterocyclization, 9,10-dimethoxy-12,13-dihydro-7aH,15H-naphtho[1',2':5,6][1,3]oxazino-[2,3-a]isoquinolines, were
isolated on condensing 6,7-dimethoxy-3,4-dihydroisoquinoline with 1-dimethylaminomethyl-2-naphthols. In the case of o-hydroxybenzyl alcohols products of a Michael aza reaction, 2-[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenols
were obtained. 相似文献
3.
Aksenov N. A. Malyuga V. V. Abakarov G. M. Aksenov D. A. Voskressensky L. G. Aksenov A. V. 《Russian Chemical Bulletin》2019,68(5):1047-1051
Russian Chemical Bulletin - A new method for the synthesis of 6,7-dimethoxy-3,4-dihydroisoquinoline based on the reaction of 2-(3,4-dimethoxyphenyl)ethan-1-amine (homoveratrylamine) with aliphatic... 相似文献
4.
É. A. Markaryan Zh. S. Arustamyan S. S. Vasilyan 《Chemistry of Heterocyclic Compounds》1973,9(5):624-627
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-4-spirocyclopentane was obtained by condensation of 3,4-dimethoxyphenyl-1-(aminomethyl)cyclopentane with formalin. The corresponding amides, which were reduced to tertiary amines, were synthesized by reaction of the latter with the acid chlorides of substituted benzoic and phenylacetic acids. Substituted dibenzo[a,-g]quinolizines, isoindolo[1,2-a]isoquinolines, and 1-(3,4-dimethoxyphenyl)-1-[(6,7-dimethoxy-1, 2,3,4-tetrahydro-2-isoquinolinyl)methyl]cyclopentane were synthesized, respectively, by condensation of 1-aryl (or aralkyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-4-spirocyclopentanes and their open analog -1-(3,4-dimethoxyphenyl)-1-(3,4-dimethoxyphenylethylaminomethyl)cyclopentane — with formalin.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 679–682, May, 1973. 相似文献
5.
V. V. Davydov V. I. Sokol E. V. Balebanova Yu. V. Shklyaev V. F. Zakharov S. L. Kuznetsov B. E. Zaitsev 《Chemistry of Heterocyclic Compounds》1995,31(7):803-812
The crystalline and molecular structure of 3,3-dimethyl-6,7-dimethoxy-1-(4,4-dimethylcyelohexa-2,6-dion-1-yl)-3,4-dihydroisoquinoline (I) have been determined. The effects of 6- and 7- substituents on the structure and tautomeric conversion of 3,3-dimethyl-1-(4,4-dimethylcyclohexa-2, 6-dion-1-yl)-3, 4-dihydroisoquinoline in solution have been studied by IR, electronic, x-ray electronic, and NMR spectroscopy and using quantumchemical calculations in the MNDO/H approximation. It was found that I exists in the enamine-diketone tautomeric form in the crystalline state and in solution. The 6- and 7- substituents cause a change in molecular conformation and a corresponding redistribution of electron density.Russian University of National Friendship, Moscow 117198. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow 117000. Institute of Technical Chemistry, Ural Section, Russian Academy of Sciences, Perm' 614600. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–933, July, 1995. Original article submitted April 15, 1995. 相似文献
6.
A new Synthesis of 8-Hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline Vilsmeier formylation of N-[2-(3,5-dimethoxyphenyl)ethyl]-trifluoroacetamide ( 5 ) yielded the aldehyde 6 , which under mild basic conditions was hydrolyzed to 7 and cyclized to 6,8-dimethoxy-3,4-dihydroisoquinoline ( 3 ). Methylation of 3 and reduction of the double bond in 10 afforded 6,8-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline ( 11 ). The methoxyl group at C(6) was selectively demethylated and the free hydroxyl group in 12 was phosphorylated to give 13 . Reduction of the latter with potassium in liquid ammonia yielded 8-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline ( 2 ), which was demethylated to the title compound 1 . 相似文献
7.
An efficient and facile procedure for the preparation of 1-[2-(6,7-dimethyl-3,4-dihydronaphthalen-2-yl)ethyl]pyrrolidine hydrochloride
from 6,7-dimethyl-1,2,3,4-tetrahydronaphtalen-1-one in four steps is proposed. It includes one-step synthesis of 1-(6,7-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic
acid as key intermediate and subsequent transformations of functional groups therein.
Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 3, pp. 449–453.
The text was submitted by the authors in English. 相似文献
8.
When 1-allyl-2-methyl-1,2-dihydropapaverine is treated with hot, dilute mineral acid, rearrangement occurs to give, almost exclusively the 3-allyl-2-methyl-3,4-dihydropapaverinium salt. The previously reported rearrangement of 1-cinnamyl-2-methyl-6,7-dimethoxy-1,2-dihydroisoquinoline has been re-examined and the earlier result, that rearrangement occurs yield the 3-cinnamyl-3,4-dihydroisoquinolinium salt, confirmed. 相似文献
9.
Gibson HW Berg MA Dickson JC Lecavalier PR Wang H Merola JS 《The Journal of organic chemistry》2007,72(15):5759-5770
Chiral acid chlorides were reacted with isoquinoline and 6,7-dimethoxy-3,4-dihydroisoquinoline to form diastereomeric Reissert compounds 8-11 and 18-21, respectively. The best diastereoselectivity (80:20) was achieved in formation of the 9-phenylmenthyl derivative 20. The diastereomers of 2-l-menthoxycarbonyl-1,2-dihydroisoquinaldonitriles (S)-8/(R)-8), formed in equal amounts, were inseparable. However, the individual diastereomers of 2-cholesteryloxycarbonyl-1,2-dihydroisoquinaldonitriles ((R)-11 and (S)-11) and the 2-l-menthoxycarbonyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinaldonitriles ((S)-19/(R)-19)) were each readily purified. (S)-8/(R)-8 (1:1) via the corresponding anions (NaH, -40 degrees C, DMF) with pivaldehyde yielded in 82:18 predominance the S-diastereomer of 1-isoquinolyl tert-butyl carbinyl l-menthyl carbonate ((S)-12), which was obtained in pure form by a single recrystallization; hydrolysis produced 99% pure S-(-)-1-isoquinolyl tert-butyl carbinol [(S)-16]. Reactions of the anions of diastereomeric Reissert compounds, either as mixtures or pure single species, with aromatic aldehydes and alkyl halides proceeded with at best modest selectivity (diastereomeric ratios up to 66:34 and 72:28, respectively). Therefore, it is concluded that the Reissert anions are either planar or rapidly inverting tetrahedral structures. 相似文献
10.
A. S. Golubev N. D. Chkanikov M. Yu. Antipin Yu. T. Struchkov A. F. Kolomiets A. V. Fokin 《Russian Chemical Bulletin》1992,41(8):1425-1429
Condensation of methyl trifluoropyruvate with 2-(3,4-dimethoxyphenyl)ethylamine, tryptamine, and (D, L)-tryptophan yielded 1-methoxycarbonyl-1-trifluoromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, 1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, and Z-1-methoxycarbonyl-1-trifluoromethyl-3-carboxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, respectively. The Z configuration of the latter was determined by x-ray structural analysis.A. N. Nesmayanov Institute of Organoelemental Compounds, Russian Academy of Sciences, 117813 Moscow, Russia. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 8, pp. 1831–1836, August, 1992. 相似文献
11.
Su-Dong Cho Deok-Heon Kweon Young-Jin Kang Sang-Gyeong Lee Woo Song Lee Yong-Jin Yoon 《Journal of heterocyclic chemistry》1999,36(5):1151-1156
Some 6,7-dimethoxy-1-halobenzyl-1,2,3,4-tetrahydroisoquinolines were synthesized from 2-(3,4-dimethoxyphenyl)ethylamine and halophenylacetic acids in three steps in good yield. 相似文献
12.
Z. G. Aliev S. N. Shurov V. A. Glushkov L. N. Karpova Yu. S. Andreichikov L. O. Atovmyan 《Russian Chemical Bulletin》1997,46(10):1751-1754
The reaction of 5-phenyl-2,3-dihydrofuran-2,3-dione with 6,7-dimethoxy-3,4-dihydroisoquinoline gave 1-benzoyl-2-hydroxy-8,9-dimethoxy-3,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3-one and its oxidation product,viz., 1-benzoyl-8,9-dimethoxy-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-dione. The last-mentioned compound was studied by X-ray structural analysis.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1845–1848, October, 1997. 相似文献
13.
Khasanov A. F. Slepukhin P. A. Kopchuk D. S. Krinochkin A. P. Kovalev I. S. Zyryanov G. V. Kim G. A. Rusinov V. L. Chupakhin O. N. 《Russian Journal of Coordination Chemistry》2019,45(2):92-96
Russian Journal of Coordination Chemistry - The structure of the cadmium(II) iodide complex with 3,4-diphenyl-1-(pyridin-2-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine is studied and determined by... 相似文献
14.
A complete NMR analysis with full assignment for (1)H and (13)C NMR spectral data for 5-(acetyloxy)-3-hydroxy-9,10-dimethoxy-6-oxo-11-oxatricyclo[6.2.1.0(2,7)]undec-2-yl acetate is described. This compound was prepared by rapid hydrogenation of the unstable Diels-Alder adduct obtained from the reaction between 3,4-dimethoxyfuran and 2,5-diacetoxy-1,4-benzoquinone. Full homonuclear hydrogen coupling constants measurements and molecular mechanics calculations were performed for the determination of the relative stereochemistry. 相似文献
15.
Su-Dong Cho Sung-Kyu Kim Hyun-A Chung Young-Jin Kang Yong-Jin Yoon 《Journal of heterocyclic chemistry》1999,36(1):75-80
Some 6,7-dimethoxy-1-[(halophenoxy)methyl]-1,2,3,4-tetrahydroisoquinolines were synthesized from N-[2-(3,4-dimethoxyphenyl)ethyl]-2-chloroacetamide via three steps in good yield. 相似文献
16.
New reactions of 6,7-dimethoxy-3,4-dihydroisoquinoline and 3,4-dihydro-β-carboline with various electron-deficient olefins are described. ‘One-pot’ generation and cycloaddition of the 1,3- and 1,4-dipoles formed from these heterocycles with a range of alkene dipolarophiles affords cycloadducts in good yields with high regio- and stereoselectivity. 相似文献
17.
Paek IB Ji HY Kim MS Lee G Lee HS 《Rapid communications in mass spectrometry : RCM》2006,20(9):1457-1462
HM-30181, 4-oxo-4H-chromene-2-carboxylic acid, [2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-2H-tetrazol-5-yl)-4,5-dimethoxyphenyl]amide, is a new P-glycoprotein inhibitor. This study was performed to identify the in vitro and in vivo metabolic pathway of HM-30181 in rats. Rat liver microsomal incubation of HM-30181 in the presence of NADPH resulted in the formation of four metabolites, M1-M4. M1 and M2 were identified as 2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-2H-tetrazol-5-yl)-4,5-dimethoxyaniline and 4- or 5-O-desmethyl-HM-30181, respectively, on the basis of liquid chromatography/tandem mass spectrometry (LC/MS/MS) analysis with the synthesized authentic standards. M3 and M4 were suggested to be 6- or 7-O-desmethyl-HM-30181 and hydroxy-HM-30181, respectively. These in vitro metabolites were also detected in feces and urine samples after an intravenous administration of HM-30181 to male rats. The metabolic routes for HM-30181 were O-demethylation of the methoxy group to M2 and M3, hydrolysis of the amide group to M1, and hydroxylation to M4. 相似文献
18.
Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones. I. 3-unsubstituted compounds
David T. Connor Paul C. Unangst Charles F. Schwender Roderick J. Sorenson Mary E. Carethers Chester Puchalski Richard E. Brown 《Journal of heterocyclic chemistry》1984,21(5):1557-1559
Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones via a Pechmann condensation of 3-carbethoxy-1-methyl-4-piperidone with various phenols is described. The limitations of this method are discussed. Synthesis of the parent ring system 3a via reduction of 1,2,3,4-tetrahydro-3-(phenylmethyl)-8-[(1-phenyl-1H-tetrazol-5-yl)oxy]-5H-[1]benzopyrano[3,4-c]pyridin-5-one ( 5 ) is also described. 相似文献
19.
Fatma M. Saleh Hamdi M. Hassaneen Holger Butenschön Gerald Dräger Ismail A. Abdelhamid 《Tetrahedron letters》2019,60(46):151265
Herein, we report the first synthesis of 10b-azachrysenes via the Hantzsch-like reaction of aldehydes with 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile and dimedone in the presence of acetic acid. The regioselectivity was established using X-ray crystallography and 2D-HMBC spectroscopy. 相似文献
20.
A. A. Aghekyan E. A. Arakelyan G. A. Panosyan A. G. Khachatryan E. A. Markaryan 《Chemistry of Heterocyclic Compounds》2009,45(9):1069-1074
1-[(3,4-Dimethoxyphenyl)cyclopentyl]methylamine has been used in the synthesis of 6,7-dimethoxy-4-spirocyclopentane-1,2,3,4-tetrahydroisoquinoline-1-carboxylic
acid N-methylamide which is employed in the preparation of novel derivatives with substituents in positions 1,2,6, and 7. 相似文献