Hindered rotation in substituted 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines

Dalton, David R.; Ramey, Kermit C.; Gisler, Henry J.; Lendvay, Louis J.; Abraham, Annama

doi:10.1021/ja01051a031

Cited by 19 publications

(5 citation statements)

References 3 publications

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“…he study of chemical-exchange phenomena in modifying line shapes of nuclear magnetic resonance (nmr) spectra is highly developed both from the theoretical and experimental points of view.2-16 At this point most applications of the technique have been accomplished in the study of hindered-rotation barriers or ring-inversion phenomena, where for the most part the mechanism of the kinetic process is either not in doubt3•5'7'8•14-17 or resolves itself into simple alternatives. [18][19][20] In cases where the mechanism of the intra-…”

Section: Discussionmentioning

confidence: 99%

Nitration of benzenesulfonate ion in acidic nitrate melts

Schlegel¹,

Robinson²

1973

J. Am. Chem. Soc.

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The nitration of benzenesulfonate and some benzenesulfonate derivatives in pyrosulfate-sulfate buffer solutions of NaN08-KN03 melts was studied in the temperature range 240-270". Products of the reaction were determined by ion-exchange chromatography and ultraviolet spectrophotometry. The reaction follows pseudofirst-order kinetics in the presence of excess benzenesulfonate as measured by the decrease in melt acidity with time. The variation in observed rate as a function of benzenesulfonate and sulfate concentrations is consistent with a mechanism involving an intermediate NO2+. BS-complex. Based on a steady-state approximation for the concentration of this intermediate, several of the rate constants involved have been evaluated. Several aspects of the reaction not unambiguously defined by the kinetics are discussed, along with some preliminary findings on related reactions in substituted benzenesulfonate. n recent years there has developed a substantial

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Section: Discussionmentioning

confidence: 99%

Nitration of benzenesulfonate ion in acidic nitrate melts

Schlegel¹,

Robinson²

1973

J. Am. Chem. Soc.

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“…1-(6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone ( 6 а ): known compound [ 49 , 50 , 51 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines

Ivanov¹,

Nikolova²,

Aladjov³

et al. 2011

Molecules

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A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydro-isoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of ketoamides with organomagnesium compounds, followed by cyclization in the presence of catalytic amounts of p-toluenesulfonic acid (PTSA). A number of substituents at the C-1 in the isoquinoline skeleton were introduced varying either carboxylic acid or organomagnesium compound. Some of the obtained 1,1-dialkyl-1,2,3,4-tetrahydro-isoquinolines possess contractile activity against guinea pig’s gastric smooth muscle preparations.

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“…7-Benzyloxy-l-(2'-bromo-4',5'-dimethoxybenzyl)-l,2,3,4-tetrahydro-6-methoxyisoquinoline (15).12 Sodium borohydride (2.50 g, 65.8 mmol) was added portionwise at room temperature to a stirred solution of 7-benzyloxy-l-(2'-bromo-4',5'-dimethoxybenzyl)-3,4-dihydro-6-methoxyisoquinoline hydrochloride monohydrate (14• 20, 3.38 g. 6.14 mmol) in methanol (40 ml) and water (5 ml). Stirring was maintained for 0.5 hr followed by refluxing for an additional 1 hr.…”

Section: Methodsmentioning

confidence: 99%

“…The solution was cooled and crystallization was induced by scratching the vessel wall, giving 2.77 g (90.6%) of colorless bromotetrahydroisoquino- (s, 3 H, OCHs), 3.84 (s, 3 H, OCH3), 4.00-4.34 (m, 1 , 1-H), 5.09 (s, 2 H, OCH2C6H5), 6.61 (s, 1 H, ArH), 6.73 (s, 1 H, ArH), 6.77 (s. 1 H, ArH), 7.03 (s, 1 H. ArH), and 7.20-7.56 (m, 5 H, OCH2C6Hs); mass spectrum m/e (rel intensity) 499 (<1), 498 (<1), 497 (<1), 496 (<1), 417 (2), 416 (5), 326 (1), 268 (100), 231 (2), 229 (2), 177 (23). 176 (9), 148 (14), and 91 (15).…”

Section: Methodsmentioning

confidence: 99%

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Synthetic approach to aporphine alkaloids. New tetracyclic benzodiazephine derivative from the benzyne cyclization of a bromophenolic 1-benzyltetrahydroisoquinoline

Spangler¹,

Boop²,

Kim³

1974

J. Org. Chem.

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The synthesis of aporphine alkaloids by the benzyne reaction of bromophenolic 1-benzyltetrahydroisoquinolines containing a carbethoxy protecting group on the isoquinoline nitrogen was examined. The benzyne reaction of l-(2'-bromo-4',5'-dimethoxybenzyl)-2-carbethoxy-l,2,3.4-tetrahydro-7-hydroxy-6-methoxyisoquinoline (8) gave a new tetracyclic benzylisoquinoline derivative. 17, in good yield. Aryl-aryl coupling via intramolecular attack of phenoxide on the intermediate aryne to give the N-carbethoxynoraporphine 9 was not observed. This process provides a useful new synthesis of certain benzodiazepines.

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Hindered rotation in substituted 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines

Cited by 19 publications

References 3 publications

Nitration of benzenesulfonate ion in acidic nitrate melts

Nitration of benzenesulfonate ion in acidic nitrate melts

Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines

Synthetic approach to aporphine alkaloids. New tetracyclic benzodiazephine derivative from the benzyne cyclization of a bromophenolic 1-benzyltetrahydroisoquinoline

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