1970
DOI: 10.1016/s0040-4039(00)99989-1
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Aporphines VI. A novel synthesis of 7-hydroxyaporphine, 7-hydroxynoraporphine and 6a,7-dehydronoraporphine

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Cited by 16 publications
(16 citation statements)
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“…The experiments were designed to remove the O -methyl groups in ring D of crebanine in order to acquire more aporphine derivatives (Scheme 2). Table 3 shows all of reactions and their derivatives [17,18,19,20,21,22]. Since ring B was unstable and easy to open using strong acids, it was difficult to cleave the O -methyl groups in ring D when only strong acids (48%HBr/CH 3 COOH, 48%HBr, and IH) were used [17,18,19].…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The experiments were designed to remove the O -methyl groups in ring D of crebanine in order to acquire more aporphine derivatives (Scheme 2). Table 3 shows all of reactions and their derivatives [17,18,19,20,21,22]. Since ring B was unstable and easy to open using strong acids, it was difficult to cleave the O -methyl groups in ring D when only strong acids (48%HBr/CH 3 COOH, 48%HBr, and IH) were used [17,18,19].…”
Section: Resultsmentioning
confidence: 99%
“…Table 3 shows all of reactions and their derivatives [17,18,19,20,21,22]. Since ring B was unstable and easy to open using strong acids, it was difficult to cleave the O -methyl groups in ring D when only strong acids (48%HBr/CH 3 COOH, 48%HBr, and IH) were used [17,18,19]. Otherwise, when crebanine was treated with BBr 3 in dichloromethane, a molecular ion peak of the products was observed at m/z 300 [M + H] + , which implies that both the O -methyl groups and methylenedioxy of crebanine had been removed simultaneously.…”
Section: Resultsmentioning
confidence: 99%
“…employing similar routes to that presented in Scheme 8, which were subjected to pharmacological evaluation in order to determine their emetic, dopaminergic, and antinociceptive activities. [74][75][76][77][78][79] Neumeyer and Granchelli published a communication in 1970 [80] and a full paper in 1974 [81] addressing the synthesis of (�)-7-hydroxyaporphine ((�)-43), (�)-7-hydroxynoraporphine ((�)-44), and 6a,7-dehydronoraporphine (45) involving the simultaneous protection of the labile hydroxyl group and secondary amino group via the formation of an oxazolonecontaining intermediate. 1-(2-Nitrobenzyl)isoquinoline (35) was oxidized to give ketone 37, which was then reduced to alcohol 38.…”
Section: Pschorr Reactionmentioning
confidence: 99%
“…The experiments were designed to remove the O-methyl groups in ring D of crebanine in order to acquire more aporphine derivatives (Scheme 2). Table 3 shows all of reactions and their derivatives [17][18][19][20][21][22]. Sincering B was unstable and easy to open using strong acids, it was difficult to cleave the O-methyl groups in ring D when only strong acids (48%HBr/CH3COOH, 48%HBr, and IH) were used [17][18][19].…”
Section: Ring D O-demethylation and Antiarrhythmic Activitymentioning
confidence: 99%
“…Table 3 shows all of reactions and their derivatives [17][18][19][20][21][22]. Sincering B was unstable and easy to open using strong acids, it was difficult to cleave the O-methyl groups in ring D when only strong acids (48%HBr/CH3COOH, 48%HBr, and IH) were used [17][18][19]. Otherwise, when crebanine was treated with BBr3 in dichloromethane, a molecular ion peak of the products was observed at m/z 300 [M + H] + , which implies that both the O-methyl groups and methylenedioxy of crebanine had been removed simultaneously.…”
Section: Ring D O-demethylation and Antiarrhythmic Activitymentioning
confidence: 99%