Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-β-hydroxyphenethylamines as starting materials for the preparation of 4-aryl-1,2,3,4-tetrahydroisoquinolines

doi:10.1016/J.TETLET.2013.03.076

Paper

DOI: 10.1016/J.TETLET.2013.03.076

Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-β-hydroxyphenethylamines as starting materials for the preparation of 4-aryl-1,2,3,4-tetrahydroisoquinolines

Published May 22, 2013 · V. Moshkin, V. Sosnovskikh

Tetrahedron Letters

Q3 SJR score

Citations

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

Study Snapshot

This study presents a new route to N-benzyl--hydroxyphenethylamines, which can be used to prepare 4-aryl-1,2,3,4-tetrahydroisoquinolines in moderate to good yields.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Full text analysis coming soon...

References

DOI: 10.1016/J.TETLET.2013.02.087

A one-pot synthesis of tetrahydroisoquinolin-4-ols via a novel acid-catalyzed rearrangement of 5-aryloxazolidines

This study presents a one-pot synthesis of tetrahydroisoquinolines using a novel acid-catalyzed rearrangement of 5-aryloxazolidines, enabling efficient production of 2-methyl-1,2,3,4-tetrahydroisoquinolin-4-o

2013·20citations·V. Moshkin et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1016/j.bmcl.2012.09.050

4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors.

4-phenyl tetrahydroisoquinolines show potential as dual norepinephrine and dopamine reuptake inhibitors, with potential applications in neuropharmacology.

2012·15citations·A. D. Pechulis et al.·Bioorganic & medicinal chemistry letters

Bioorganic & medicinal chemistry letters

DOI: 10.1016/J.TETLET.2012.05.008

Nucleophilic properties of a nonstabilized azomethine ylide derived from sarcosine and cyclohexanone. A novel domino reaction leading to substituted 4-aryl-2-pyrrolidones

A nonstabilized azomethine ylide from sarcosine and cyclohexanone can react with 3-substituted coumarins and ethyl benzylidene malonate to produce 4-aryl-2-pyrrolidones,

2012·20citations·V. Moshkin et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1002/asia.200900470

Enantiospecific stereodivergent synthesis of trans- and cis-N(2),3-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines.

Acid-promoted cyclization of N-benzylethanolamines and their chromium tricarbonyl complexes leads to the enantiospecific synthesis of trans- and cis-N(2),3-dimethyl-4-phenyl-1,2,3,4-te

2010·17citations·S. Coote et al.·Chemistry, an Asian journal

Chemistry, an Asian journal

DOI: 10.1016/J.TET.2009.01.098

Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates

This study developed a simple, efficient method for synthesizing 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines using readily available starting materials and three steps.

2009·19citations·J. Crecente‐Campo et al.·Tetrahedron

Tetrahedron

DOI: 10.1071/CH07282

Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes

N-benzyl-5-aryloxazolidines 1 are synthesized by the 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide with aromatic aldehydes, yielding N-benzyl-5-aryloxazol

2007·23citations·J. H. Ryan et al.·Australian Journal of Chemistry

Australian Journal of Chemistry

DOI: 10.1021/OP700183Q

A Practical Synthesis of Enantiopure 7-Alkoxy-4-aryl-tetrahydroisoquinoline, a Dual Serotonin Reuptake Inhibitor/Histamine H3 Antagonist

The efficient synthesis of 7-Alkoxy-4-aryl-tetrahydroisoquinoline, a dual serotonin reuptake inhibitor/histamine H3 antagonist, offers a promising route for large-scale production.

2007·18citations·Xiaohu Deng et al.·Organic Process Research & Development

Organic Process Research & Development

DOI: 10.1016/S0040-4020(03)01236-5

Highly stereoselective Friedel–Crafts type cyclization. Facile access to enantiopure 1,4-dihydro-4-phenyl isoquinolinones

This study presents a highly stereoselective Friedel-Crafts type cyclization method for facile access to enantiopure 1,4-dihydro-4-phenyl isoquinolinones, with amide carbonyl being crucial for ensuring stereospecificity during electrophil

2003·30citations·N. Philippe et al.·Tetrahedron

Tetrahedron

DOI: 10.1002/CHIN.200146081

A New and Convenient Synthesis of 1-Aryl-2-dimethylaminoethanols

This study presents a new and convenient method for the synthesis of 1-aryl-2-dimethylaminoethanols, offering a new approach for the synthesis of pharmaceuticals and nutraceuticals.

2001·19citations·M. Nyerges et al.·ChemInform

ChemInform

Citations

DOI: 10.59761/rcr5125

The chemistry of heterocycles in the 21st century

Russian chemists have made significant advances in heterocycle chemistry over the last 15-20 years, leading to new drug design, high-energy molecules, and materials for organic electronics and photovoltaics.

2024·6citations·V. N. Charushin et al.·Russian Chemical Reviews

Russian Chemical Reviews

DOI: 10.1016/J.TETLET.2018.03.037

Novel synthesis of aminoacetonitriles via the selective demethylation of quaternary ammonium salts

Selective demethylation of quaternary ammonium salts in dimethylformamide leads to moderate to good yields of aminoacetonitriles (36-69%) from N-methyl cyclic amines.

2018·4citations·E. Buev et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1016/J.MENCOM.2017.11.031

A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines

This novel diastereoselective -functionalization of proline with benzaldehydes enables the synthesis of -(-hydroxybenzyl)prolines with a preference for one diastereomer and overall yield of 33-50%.

2017·3citations·A. V. Pavlushin et al.·Mendeleev Communications

Mendeleev Communications

DOI: 10.1021/acs.joc.7b02193

Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids.

The Mannich reaction-dipolar cycloaddition method efficiently synthesizes 3,3-disubstituted pyrrolidines, including oxindole alkaloids, with a single activated hydrogen.

2017·24citations·E. Buev et al.·The Journal of organic chemistry

The Journal of organic chemistry

DOI: 10.1016/J.TETLET.2016.07.007

Spiroanthraceneoxazolidine as a synthetic equivalent of methanimine in the reaction with donor–acceptor cyclopropanes. Synthesis of diethyl 5-arylpyrrolidine-3,3-dicarboxylates

Spiroanthraceneoxazolidine effectively synthesizes diethyl 5-arylpyrrolidine-3,3-dicarboxylates in a one-pot domino reaction, yielding 16-54% functionalized arylpyrrolidines in 16-54% yields.

2016·8citations·E. Buev et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.3390/molecules21080935

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

This study provides a comprehensive account of 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles, yielding oxazolidine derivatives, which undergo various reactions triggered by ring-opening of the oxa

2016·65citations·A. G. Meyer et al.·Molecules

Molecules

DOI: 10.1021/acs.orglett.6b00475

Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines.

Spiroanthraceneoxazolidines effectively trap nonstabilized azomethine ylides, enabling their storage and regeneration in moderate to high yields, with potential for low reactive dipolarophiles.

2016·31citations·E. Buev et al.·Organic letters

Organic letters