Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation DOI Creative Commons
Veera Babu Gudise, Shaik Anwar

RSC Advances, Journal Year: 2023, Volume and Issue: 13(39), P. 27456 - 27460

Published: Jan. 1, 2023

AB 2 C type four component quadruple cascade reaction between MBH acetate, 1,3-indanedione and aldehydes via [1 + 1 3] annulation progressed through Knoevenagel/Michael/Michael/Michael sequence for the synthesis of b is-spirocyclohexane.

Language: Английский

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

Jing Sun,

Xueyan Liu, Qiu Sun

et al.

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

Citations

23
The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
TiO2/RuO2/CuO catalysed green synthesis of novel spiropyrrolizidines and their anticancer activity: Synthesis, single crystal X-ray diffraction, DFT, Hirshfeld and molecular docking studies. DOI
Mohammad Asad, Muhammad Nadeem Arshad, Naved Azum

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141955 - 141955

Published: March 1, 2025

Language: Английский

Citations

0
Indane-1,3-dione: Versatile precursor for the microwave-assisted synthesis of annulated and spiro-molecular systems DOI
Sherif M. H. Sanad,

Ibrahim S. Sanad

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 27

Published: April 17, 2025

Language: Английский

Citations

0
Discovery and optimization of 2-pyridones as dual h-DHFR/EGFRTK inhibitors with immunomodulatory potential; Design, synthesis, anti-proliferative activity, and apoptosis inducer DOI
Ahmed Ragab, Reham R. Raslan,

Moustafa S. Abusaif

et al.

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 117751 - 117751

Published: May 1, 2025

Language: Английский

Citations

0
Annulations involving 1-indanones to access fused- and spiro frameworks DOI Creative Commons
Suven Das, Arpita Dutta

RSC Advances, Journal Year: 2022, Volume and Issue: 12(51), P. 33365 - 33402

Published: Jan. 1, 2022

This review highlights recent (2016–2022) annulations of 1-indanones for the construction various fused- and spiro carbo- heterocyclic frameworks.

Language: Английский

Citations

10
Organocatalytic Vinylogous Michael Addition/Cyclization Cascade of 2‐Alkylidene Indane‐1,3‐diones with Enals: A Regio‐ and Stereocontrolled Diversity‐Oriented Route to Indane‐1,3‐dione Derivatives DOI Open Access

Jen‐Yu Kuan,

I‐Ting Chen,

Hsuan Lin

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3493 - 3504

Published: Aug. 26, 2023

Abstract A substrate‐dependent, regio‐ and stereocontrolled diversity‐oriented organocatalytic vinylogous Michael addition/cyclization cascade of 2‐alkylidene indane‐1,3‐diones with enals, using secondary amines as the catalyst, has been developed. This allows synthesis spiroindane‐1,3‐diones, tetrahydrofluoren‐9‐one derivatives, benzofused oxabicyclo[3.3.1]nonanes in a highly selective manner. Plausible catalytic pathways for formation these biologically interesting compounds were proposed. Density functional theory (DFT) calculations have clarified supported mechanisms how organocatalyst is able to activate enals 2‐hydroxycinnamaldehydes, directing C−C bond forming dienolates enabling derivatives.

Language: Английский

Citations

5
Rhodium-catalyzed annulation for the construction of indole core: An update DOI
Suven Das, Arpita Dutta

Tetrahedron, Journal Year: 2023, Volume and Issue: 146, P. 133633 - 133633

Published: Sept. 11, 2023

Language: Английский

Citations

4
Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules DOI
Suven Das

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(18), P. 8243 - 8276

Published: Jan. 1, 2024

The present review summarizes the recent advances (2018–2023) in stereoselective annulation involving p -benzoquinones for construction of fused, spiro and bridged/cage frameworks.

Language: Английский

Citations

1
A Synthetic Route Towards Spiro Indanone Fused Pyrano[2,3‐c]Chromene Derivatives via Oxa–Diels–Alder Reaction: Computational Investigation, Antibacterial Evaluation and Molecular Docking Studies as Potential DNA Gyrase Inhibitors DOI Open Access
Jasmine Panda,

Beli Brahma,

Sabita Nayak

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 24, 2024

ABSTRACT A highly efficient method for the synthesis of 2′ H ‐spiro[indene‐2,3′‐pyrano[2,3‐ c ]chromene] derivatives 20(a–s) has been developed involving oxa–Diels–Alder reaction as key step under conventional conditions in good to excellent yields. The compounds were all characterized using 1 H, 13 C NMR, HRMS, and X‐ray crystallography. present study employs DFT validate pathway. In vitro antibacterial assay synthesized was evaluated against Gram‐negative Escherichia coli Gram‐positive Staphylococcus aureus bacterial strains. Compound 20e found be most potent molecule with ZI 19 mm MIC 16 μg mL −1 E. 14 32 S. . Additionally, demonstrated a strong inhibition DNA gyrase silico , binding affinity −9.3 − 9.0 kcal/mol respectively. Also, significant pharmacokinetic, physicochemical, drug‐like properties spirocyclic further corroborated by ADME investigations. Hence, these new series spiro indanone fused pyrano[2,3‐ ]chromene may druggable agents future.

Language: Английский

Citations

1