Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core

doi:10.1055/s-0037-1610999

Paper

Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core

Published Nov 14, 2018 · Prashishkumar K. Shirsat, Navnath B. Khomane, Sneha H Meshram

Synthesis

Q2 SJR score

5

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0

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Abstract

Abstract A novel, one-pot reaction for the synthesis of 3,4-dihydroisoquinolin-2(1H)-one derivatives is developed via a base-mediated three-component reaction of ninhydrin, aniline and acetylenic esters. This diastereoselective reaction takes place in methanol at 70 °C under transition-metal-free conditions, and direct construction of the C–N and C–C bonds is readily achieved via tandem cyclization. These cyclic frameworks are resourceful small molecular keys to many natural products.

Study Snapshot

Base-catalyzed tandem cyclization allows for the synthesis of 3,4-dihydroisoquinolin-2(1H)-one derivatives in methanol under transition-metal-free conditions, offering potential for natural product discovery.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core

References

Citations

Acetylenic Esters in Organic Synthesis

Acetylenic esters play a crucial role in organic synthesis, enabling the synthesis of various novel compounds and intermediates.

Recent applications of ninhydrin in multicomponent reactions

Ninhydrin-based multicomponent reactions have shown promise in building versatile scaffolds for organic synthesis, with potential for anticancer agents and biological activities.

Condensation of ninhydrin with phenols: Regioselective formation of diverse organic scaffolds and crystal structure studies

Ninhydrin-phenol reactions produce diverse indanone-based molecules with diverse structures and functions, depending on the substitution patterns and acidity of the reaction medium.