Stereoselective synthesis of fused-, spiro- and bridged heterocycles via cyclization of isoquinolinium salts: a recent update

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(9), P. 1838 - 1868

Published: Jan. 1, 2022

Isoquinoline and its derivatives are ubiquitous in natural alkaloids, synthetic materials pharmaceuticals with a broad spectrum of biological activities. In particular, isoquinolinium salts important organic synthesis because they can serve as building blocks for the rapid construction various condensed heterocyclic systems involving cyclization processes. This review highlights novel stereoselective strategies that emerged last few years (2014-2021) fused-, spiro- bridged heterocycles exploiting bench-stable or situ generated salts. Most reactions described here provide quick access to desired products high stereoselectivity starting from readily available under mild conditions. The potential most transformations was confirmed by gram-scale production target molecules. Some have been useful other bioactive compounds.

Language: Английский

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The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 982 - 990

Published: June 29, 2023

The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines good yields with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition acetylenedicarboxylates refluxing gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products 1,3a,4,6a-tetrahydrocyclopenta[b]pyrroles minor via further rearrangement.

Language: Английский

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Convenient generation of 1,3-dipolar nitrilimines and [3 + 2] cycloaddition for the synthesis of spiro compounds

Tetrahedron Letters, Journal Year: 2022, Volume and Issue: 110, P. 154186 - 154186

Published: Oct. 8, 2022

Language: Английский

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Six-membered ring systems: pyridines and benzo derivatives

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 387 - 424

Published: Jan. 1, 2023

Language: Английский

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