Synthesis of Novel 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid Derivatives through the Application of Rongalite: A Synergistic Combination of [2+2+2]- and [4+2]-Cycloaddition Reactions

doi:10.1055/S-2007-965946

Paper

Synthesis of Novel 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid Derivatives through the Application of Rongalite: A Synergistic Combination of [2+2+2]- and [4+2]-Cycloaddition Reactions

Published Apr 1, 2007 · S. Kotha, Shaibal Banerjee

Synthesis

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Abstract

An efficient route for the synthesis of several novel 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives has been reported. A synergistic combination of [2+2+2]- and [4+2]-cycloaddition reactions has been used for the synthesis of the desired targets.

Study Snapshot

This efficient route enables the synthesis of novel 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives with high specific activity and potential applications in various fields.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of Novel 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid Derivatives through the Application of Rongalite: A Synergistic Combination of [2+2+2]- and [4+2]-Cycloaddition Reactions

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References

Citations

Design of Synthetic Strategies towards Sulfur Containing Scaffolds

This review highlights the syntheses of diverse sulfur heterocycles embedded with complex scaffolds using various sulfur reagents and sulfur-containing starting materials for complex target molecules.

Rongalite-Mediated Transition Metal- and Hydride-Free Chemoselective Reduction of α-Keto Esters and α-Keto Amides.

This study developed a rongalite-mediated chemo selective reduction method for synthesis of -hydroxy esters and -hydroxy amides, offering 85-98% yields and compatibility with other reducible functionalities.

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Silver-mediated 1,3-acyloxy migration/Diels-Alder reaction efficiently prepares partially hydrogenated isoquinolines with good to excellent yields, even with diverse substitution patterns.

Diversity-oriented synthesis of medicinally important 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives and higher analogs.

This paper highlights the importance of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) in various biologically active compounds and provides diverse synthetic approaches for its construction, including traditional and recent methods.

Diversity-oriented approaches to unusual α-amino acids and peptides: step economy, atom economy, redox economy, and beyond.

This study presents diverse strategies for creating unusual -amino acid derivatives and peptides using atom-economic processes, enabling a library of modified amino acids and peptides.

Diversity-oriented approach to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives using diethyl acetamidomalonate as a glycine equivalent: further expansion by Suzuki-Miyaura cross-coupling reaction

Diethyl acetamidomalonate as a glycine equivalent allows for the synthesis of diverse 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives and their higher analogues, with the Suzuki-Miyaura cross-coup

Synthesis of non-proteinogenic phenylalanine derivatives by rhodium-catalyzed [2+2+2] cycloaddition reactions.

Rhodium-catalyzed [2+2+2] cycloaddition reactions efficiently produce non-proteinogenic phenylalanine derivatives with diverse substituents, making them useful for the synthesis of pharmaceuticals and nutraceuticals.

Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C–H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

Pd-catalyzed direct arylation of 3,4-dihydroisoquinolones with aryl iodides efficiently synthesizes biologically interesting 8-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields.