Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines

Zaman, Manzoor; Hasan, Muhammad; Peshkov, Anatoly A.; Puzyk, Aleksandra; Wang, Yuqing; Lim, Chang-Keun; Pereshivko, Olga P.; Peshkov, Vsevolod A.

doi:10.1016/j.tetlet.2023.154769

Tetrahedron Letters

2023

DOI: 10.1016/j.tetlet.2023.154769

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Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines

Manzoor Zaman,

Muhammad Hasan,

Anatoly A. Peshkov

et al.

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2024

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Cited by 2 publications

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Stereo‐ and Chemoselective Enrichment of sp³ Character in Post‐Ugi Morpholines

Hasan,

Nuroldayeva,

Begenov

et al. 2024

Eur J Org Chem

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We conducted a systematic study on synthesis and modification of morpholine core using Ugi adducts derived from propiolic acid and glycolaldehyde dimer. The assembly step involved triphenylphosphine‐promoted 6‐exo‐dig umpolung oxa‐Michael cyclization of Ugi‐derived hydroxypropargylamides yielding 2‐methylenemorpholin‐3‐one derivatives. Subsequent heterogeneous catalytic hydrogenation of the exocyclic double bond proceeded in a highly diastereoselective fashion establishing a relative cis configuration in the resulting sp3‐enriched morpholinone scaffold. Finally, chemoselective amide reduction with lithium aluminum hydride (LAH) allowed to obtain fully saturated morpholines while leaving the more sterically hindered exocyclic amide moiety intact. Taken together these findings outline the strategy for controlled reduction of the inherent rigidity of post‐Ugi scaffolds.

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Stereo‐ and Chemoselective Enrichment of sp³ Character in Post‐Ugi Morpholines

Hasan,

Nuroldayeva,

Begenov

et al. 2024

Eur J Org Chem

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Triflic acid-promoted post-Ugi condensation for the assembly of 2,6-diarylmorpholin-3-ones

Amire,

Almagambetova,

Turlykul

et al. 2024

Org. Biomol. Chem.

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Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines

Cited by 2 publications

References 68 publications

Stereo‐ and Chemoselective Enrichment of sp³ Character in Post‐Ugi Morpholines

Stereo‐ and Chemoselective Enrichment of sp³ Character in Post‐Ugi Morpholines

Triflic acid-promoted post-Ugi condensation for the assembly of 2,6-diarylmorpholin-3-ones

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Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines

Cited by 2 publications

References 68 publications

Stereo‐ and Chemoselective Enrichment of sp3 Character in Post‐Ugi Morpholines

Stereo‐ and Chemoselective Enrichment of sp3 Character in Post‐Ugi Morpholines

Triflic acid-promoted post-Ugi condensation for the assembly of 2,6-diarylmorpholin-3-ones

Contact Info

Product

Resources

About

Stereo‐ and Chemoselective Enrichment of sp³ Character in Post‐Ugi Morpholines

Stereo‐ and Chemoselective Enrichment of sp³ Character in Post‐Ugi Morpholines