Convenient Synthetic Protocols for Diverse Functionalized Dihydrobenzofuran-Fused Spiro-indanedione-oxindole Scaffolds

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11562 - 11580

Published: July 27, 2023

Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates isatins and 2-(o-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines] could be selectively using DABCO or DMAP as a base promoter. More importantly, facilitated the annulation MBH formates 2-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]. Additionally, similar with maleimides afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines] high yields diastereoselectivity.

Language: Английский

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Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1304, P. 137684 - 137684

Published: Feb. 4, 2024

Language: Английский

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1,3-Indanedione: An versatile building block

Green Synthesis and Catalysis, Journal Year: 2022, Volume and Issue: 4(2), P. 78 - 88

Published: Dec. 14, 2022

Indanone-containing compounds are very important components of various natural products, chemical drugs, agrochemicals and functionalized material fields. 1,3-Indanedione is a typical cyclic 1,3-dicarbonyl compound with three contiguous reactive electrophilic nucleophilic sites. The easily prepared 2-arylidene-1,3-indanediones active α,β-unsaturated carbonyl could act as 1,3-dipolarophile, 1,4-dienophile 1-oxa-1,3-diene, etc. On the other hand, homodimer (bindone) cyclotrimer (truxenone) derived from base-catalyzed self-condensation 1,3-indanedione also compounds. Therefore, its derivatives can be employed key substrates in domino multicomponent reactions. In this review, we summarized recent progress on reactions 1,3-indanedione, especially our achievements synthetic applications for complex indanone-containing carbocyclic heterocyclic

Language: Английский

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Construction of Unique Spiro[dibenzo[a,f]azulene-6,2′-indenes] via Unprecedented Annulation of ortho-C–H Bond of Benzylidene Group

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 14911 - 14927

Published: Oct. 23, 2023

The domino reaction of alkyl and aryl isocyanides with two molecules 2-arylidene-1,3-indanediones in acetonitrile at 80 °C resulted unique functionalized spiro[dibenzo[a,f]azulene-6,2'-indenes] good yields, which the acted as different building blocks to construct polycyclic system. More importantly, unprecedented anticipation ortho-position benzylidene group form a novel dibenzo[a,f]azulene ring through formal [5 + 2] cycloaddition process was first observed. On other hand, DABCO-promoted afforded spiro[cyclopenta[a]-indene-2,2'-indene] derivatives.

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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Selective synthesis of multifunctionalized cyclopent-3-ene-1-carboxamides and 2-oxabicyclo[2.2.1]heptane derivatives

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(36), P. 17161 - 17166

Published: Jan. 1, 2022

Triethylamine promoted cycloaddition reaction of phenacylmalononitrile with o -hydroxychalcones or chalcone -enolates to selectively give cyclopent-3-ene-1-carboxamides and 2-oxabicyclo[2.2.1]heptanes.

Language: Английский

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