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W. Th. Nauta - One of the best experts on this subject based on the ideXlab platform.
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Derivatives of benzo‐ and indolo‐Quinolizines: I Synthesis of 2‐substituted hexahydro‐2H‐benzo[a]Quinolizines and octahydroindolo[2,3‐a]Quinolizines from substituted glutaric acids
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, W. Th. NautaAbstract:The preparation of a number of 2-substituted 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]Quinolizines and 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]Quinolizines is described. Starting from 3-substituted valerolactones, the preparation required five stages (see Reaction Scheme I). A number of the 3-substituted valerolactones used were conveniently prepared by reduction of the corresponding glutaric acid derivatives, e.g. the anhydrides, with sodium borohydride. The final stage is a stereoselective reduction, leading to cis or trans isomers. The synthesis and data of one of the end-products, 1,3,4,6,7,11b-hexahydro -9,10-dimethoxy-2-phenyl-2H-benzo[a]quinolizine, are compared with those reported for this compound by Tomimatsu.
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Derivatives of benzo‐ and indolo‐Quinolizines IV: Synthesis of some 1‐ or 3‐substituted hexahydro‐2H‐benzo[a]‐Quinolizines and octahydroindolo[2,3‐a]Quinolizines
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, W. Th. NautaAbstract:The preparation of some derivatives of 1,3,4,6,7,1 1b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine and 1,2,3,4,6,7,12,12b-octahydroindolo-[2,3-a]quinolizine substituted with two alkyl groups, either in the 1- or the 3-position is described. Two reaction routes were followed for each of the two types of compounds and some of the numerous intermediates have been isolated.
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Derivatives of benzo- and indolo-Quinolizines. III: The stereochemistry of 2-substituted hexahydro-2H-benzo[a]Quinolizines and octahydroindolo[2,3-a]Quinolizines†
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, A. De Roos, W. Th. NautaAbstract:To some of the quinolizine derivatives described earlier (1 and 2) we have been able to assign a cis or trans structure on the strength of a stereoselective synthesis. Infrared spectral data and differences in the rate of dehydrogenation, combined with a study of the conformations possible, allowed such assignment for other compounds in this series.
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Tetracyclic γ-carboline derivatives: Synthesis of 2,8-substituted octahydroindolo[3,2-α]Quinolizines
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: G. J. B. Corts, W. Th. NautaAbstract:The preparation of a number of 2,8-substituted 1,2,3,4,6,7,8,12c-octahydroindolo[3,2-α]Quinolizines, using a 2-(2-aminoethyl)indole derivative and 3-substituted glutaric anhydrides, or 3-substituted 5-bromovalerates, as starting materials, is described.
Yu. Yu. Morzherin - One of the best experts on this subject based on the ideXlab platform.
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Diastereoselective synthesis of spiro derivatives of 3-substituted 2,3,4,4a,5,6-hexahydro-1H-benzo[c]Quinolizines
Russian Journal of Organic Chemistry, 2009Co-Authors: Tatiana V. Glukhareva, E. V. Deeva, A. Yu. Platonova, I. V. Geide, Mikhail I Kodess, Yu. Yu. MorzherinAbstract:The cyclization via the mechanism of “ tert -amino effect” of 2-(4-R-piperidino)benzaldehydes with cyclic active methylene components (Meldrum’s acid, 1,3-cyclohexanedione, and N,N-disubstituted barbituric acids) proceeded stereoselectively giving spiro-joined 2,3,4,4a,5,6-hexahydro-1 H -benzo[ c ]Quinolizines with axially oriented hydrogen atoms in the positions 3 and 4a of the benzo[c]quinolizine ring.
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Stereoselective synthesis of new spiro-fused heterocyclic systems, 2,3,4,4a,5.6-hexahydro-6H-spiro[benzo[c]quinolizine-5,4′-pyrazol]-5′-ones
Chemistry of Heterocyclic Compounds, 2007Co-Authors: Tatiana V. Glukhareva, E. V. Deeva, P. E. Kropotina, M. F. Kosterina, Yu. I. Nein, Yu. Yu. MorzherinAbstract:The synthesis of 2,3,4,4a,5,6-hexahydro-6H-spiro[benzo[c]quinolizine-5,4′-pyrazol]-5′-ones has been achieved by the reaction of 2-piperidinobenzaldehydes with 2-aryl-5-methyl-2,4-dihydropyrazol-3-one via the “tert-amino effect” mechanism.
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stereoselective synthesis of new spiro fused heterocyclic systems 2 3 4 4a 5 6 hexahydro 6h spiro benzo c quinolizine 5 4 pyrazol 5 ones
Chemistry of Heterocyclic Compounds, 2007Co-Authors: Tatiana V. Glukhareva, E. V. Deeva, P. E. Kropotina, M. F. Kosterina, Yu. I. Nein, Yu. Yu. MorzherinAbstract:The synthesis of 2,3,4,4a,5,6-hexahydro-6H-spiro[benzo[c]quinolizine-5,4′-pyrazol]-5′-ones has been achieved by the reaction of 2-piperidinobenzaldehydes with 2-aryl-5-methyl-2,4-dihydropyrazol-3-one via the “tert-amino effect” mechanism.
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stereoselective synthesis of spirofused 3 substituted 2 3 4 4a 5 6 hexahydro 6h benzo c quinolizine using the tert amino effect
Mendeleev Communications, 2006Co-Authors: E. V. Deeva, Tatiana V. Glukhareva, Alexey V. Tkachev, Yu. Yu. MorzherinAbstract:The interaction of 2-(4-R-piperidino)benzaldehyde and cyclic CH-active compounds occurred as a tandem of Knovenagel condensation and cyclization by tert -amino effect and led to spiro-fused 3-substituted 2,3,4,4a,5,6-hexahydro-6 H -benzo[ c ]quinolizine.
Alessandra Silvani - One of the best experts on this subject based on the ideXlab platform.
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stereocontrolled reduction of an oxazepinohexahydroindolo 2 3 a quinolizine derivative asymmetric total synthesis of tacamonine
Tetrahedron Letters, 2001Co-Authors: Bruno Danieli, Giordano Lesma, Daniele Passarella, Alessandro Sacchetti, Alessandra SilvaniAbstract:Abstract Efficient, stereocontrolled total synthesis of the title compound is described, starting from enantiopure intermediates. A key step was the diastereoselective catalytic hydrogenation of a pentacyclic oxazepinohexahydroindolo[2,3- a ]quinolizine derivative.
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Stereocontrolled reduction of an oxazepinohexahydroindolo[2,3-a]quinolizine derivative: asymmetric total synthesis of (+)-tacamonine
Tetrahedron Letters, 2001Co-Authors: Bruno Danieli, Giordano Lesma, Daniele Passarella, Alessandro Sacchetti, Alessandra SilvaniAbstract:Abstract Efficient, stereocontrolled total synthesis of the title compound is described, starting from enantiopure intermediates. A key step was the diastereoselective catalytic hydrogenation of a pentacyclic oxazepinohexahydroindolo[2,3- a ]quinolizine derivative.
J. Gootjes - One of the best experts on this subject based on the ideXlab platform.
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Derivatives of benzo‐ and indolo‐Quinolizines: I Synthesis of 2‐substituted hexahydro‐2H‐benzo[a]Quinolizines and octahydroindolo[2,3‐a]Quinolizines from substituted glutaric acids
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, W. Th. NautaAbstract:The preparation of a number of 2-substituted 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]Quinolizines and 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]Quinolizines is described. Starting from 3-substituted valerolactones, the preparation required five stages (see Reaction Scheme I). A number of the 3-substituted valerolactones used were conveniently prepared by reduction of the corresponding glutaric acid derivatives, e.g. the anhydrides, with sodium borohydride. The final stage is a stereoselective reduction, leading to cis or trans isomers. The synthesis and data of one of the end-products, 1,3,4,6,7,11b-hexahydro -9,10-dimethoxy-2-phenyl-2H-benzo[a]quinolizine, are compared with those reported for this compound by Tomimatsu.
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Derivatives of benzo‐ and indolo‐Quinolizines IV: Synthesis of some 1‐ or 3‐substituted hexahydro‐2H‐benzo[a]‐Quinolizines and octahydroindolo[2,3‐a]Quinolizines
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, W. Th. NautaAbstract:The preparation of some derivatives of 1,3,4,6,7,1 1b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine and 1,2,3,4,6,7,12,12b-octahydroindolo-[2,3-a]quinolizine substituted with two alkyl groups, either in the 1- or the 3-position is described. Two reaction routes were followed for each of the two types of compounds and some of the numerous intermediates have been isolated.
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Derivatives of benzo- and indolo-Quinolizines. III: The stereochemistry of 2-substituted hexahydro-2H-benzo[a]Quinolizines and octahydroindolo[2,3-a]Quinolizines†
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, A. De Roos, W. Th. NautaAbstract:To some of the quinolizine derivatives described earlier (1 and 2) we have been able to assign a cis or trans structure on the strength of a stereoselective synthesis. Infrared spectral data and differences in the rate of dehydrogenation, combined with a study of the conformations possible, allowed such assignment for other compounds in this series.
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derivatives of benzo and indolo Quinolizines i synthesis of 2 substituted hexahydro 2h benzo a Quinolizines and octahydroindolo 2 3 a Quinolizines from substituted glutaric acids
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, Th W NautaAbstract:The preparation of a number of 2-substituted 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]Quinolizines and 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]Quinolizines is described. Starting from 3-substituted valerolactones, the preparation required five stages (see Reaction Scheme I). A number of the 3-substituted valerolactones used were conveniently prepared by reduction of the corresponding glutaric acid derivatives, e.g. the anhydrides, with sodium borohydride. The final stage is a stereoselective reduction, leading to cis or trans isomers. The synthesis and data of one of the end-products, 1,3,4,6,7,11b-hexahydro -9,10-dimethoxy-2-phenyl-2H-benzo[a]quinolizine, are compared with those reported for this compound by Tomimatsu.
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derivatives of benzo and indolo Quinolizines iv synthesis of some 1 or 3 substituted hexahydro 2h benzo a Quinolizines and octahydroindolo 2 3 a Quinolizines
Recueil des Travaux Chimiques des Pays-Bas, 2010Co-Authors: J. Gootjes, Th W NautaAbstract:The preparation of some derivatives of 1,3,4,6,7,1 1b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine and 1,2,3,4,6,7,12,12b-octahydroindolo-[2,3-a]quinolizine substituted with two alkyl groups, either in the 1- or the 3-position is described. Two reaction routes were followed for each of the two types of compounds and some of the numerous intermediates have been isolated.
Jan Szymoniak - One of the best experts on this subject based on the ideXlab platform.
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a hydrozirconation iodination mediated access to tetrahydroquinolizinium salts application to the synthesis of lupinine and epiquinamide
Tetrahedron Letters, 2013Co-Authors: Majdi Hajri, Clement Blondelle, Jean-luc Vasse, Agathe Martinez, Jan SzymoniakAbstract:The preparation of tetrahydroquinolizinium salts, based on a hydrozirconation/iodination sequence involving 2-pyridyl alkenes, is presented. This approach was applied to the synthesis of substituted Quinolizines as illustrated by the synthesis of Lupinine and (−)-Epiquinamide.
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A hydrozirconation/iodination-mediated access to tetrahydroquinolizinium salts. Application to the synthesis of Lupinine and (−)-Epiquinamide
Tetrahedron Letters, 2013Co-Authors: Majdi Hajri, Clement Blondelle, Jean-luc Vasse, Agathe Martinez, Jan SzymoniakAbstract:The preparation of tetrahydroquinolizinium salts, based on a hydrozirconation/iodination sequence involving 2-pyridyl alkenes, is presented. This approach was applied to the synthesis of substituted Quinolizines as illustrated by the synthesis of Lupinine and (−)-Epiquinamide.
