A gold-catalysed post-Ugi chemo- and diastereoselective cascade dearomative spirocyclization/1,6-addition sequence is disclosed for the synthesis of diverse fused polyheterocyclic scaffolds bearing indole, pyrrole, benzothiophene, furan or electron-rich arene moieties from easily available building blocks. The effectiveness and efficiency of this diversity-oriented approach has been proved in the rapid construction of 28 fused polyheterocyclic scaffolds with a good building-block variability and structural complexity in two operational steps.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c9ob01299k | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Revisiting Pyrimidine-Embedded Molecular Frameworks to Probe the Unexplored Chemical Space for Protein-Protein Interactions.
Acc Chem Res
November 2024
Department of Chemistry, Seoul National University, Seoul 08826, Korea (South).
Article Synopsis
- Protein-protein interactions (PPIs) are crucial for many biological functions and diseases, making them important but challenging targets for drug development.
- Traditional drug discovery has focused on enzymes and receptors, which have smaller binding sites, leaving a gap in strategies to successfully target PPIs.
- To overcome these challenges, a new strategy called privileged substructure-based diversity-oriented synthesis (pDOS) was developed, incorporating pyrimidine-based compounds to create diverse chemical structures that can effectively interfere with PPIs, including inhibiting the interaction between human ACE2 and the SARS-CoV-2 spike protein.
Mapping of Some Further Alkylation-Initiated Pathways to Polyheterocyclic Compounds from Indigo and Indirubin.
Molecules
September 2024
School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
The reaction of indigo with two equivalents of the electrophile ethyl bromoacetate with caesium carbonate as a base result in the formation of structurally complex polyheterocyclics, including a fused spiroimidazole and a spiro[1,3]oxazino derivative, together with a biindigoid-type derivative, through a convenient one-pot reaction. Further assessment of the reaction using five equivalents of the electrophile gave rise to other molecules incorporating the 2-(7,13,14-trioxo-6,7,13,14-tetrahydropyrazino[1,2-:4,3-']diindol-6-yl) scaffold. The reaction of ethyl bromoacetate with the less reactive indirubin resulted in the synthesis of three derivatives of a new class of polyheterocyclic system via a cascade process, although yields were low.
View Article and Find Full Text PDFComplexity-Building Exhaustive Dearomatization of Benzenoid Aromatics within an ESIPT-Initiated Three-Step Photochemical Cascade.
Angew Chem Int Ed Engl
September 2024
Department of Chemistry and Biochemistry, University of Denver, Denver, CO, 80208.
Dearomative cycloadditions offer rapid access to complex 3D molecular architectures, commonly via a sp-to-sp rehybridization of two atoms of an aromatic ring. Here we report that the 6e π-system of a benzenoid aromatic pendant could be exhaustively depleted within a single photochemical cascade. An implementation of this approach involves the initial dearomative [4+2] cycloaddition of the Excited State Intramolecular Proton Transfer (ESIPT)-generated azaxylylene, followed by two consecutive [2+2] cycloadditions of auxiliary π moieties strategically positioned in the photoprecursor.
View Article and Find Full Text PDFUltrasound-assisted diastereoselective green synthesis of spiro-fused-γ-lactams functionalized with an amide bond heterocyclic bioisostere the Ugi azide/domino process coupled strategy.
Org Biomol Chem
July 2024
Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato C.P. 36050, Gto., Mexico.
A series of linked-type 1,5-disubstituted tetrazoles (1,5-DS-Ts) were synthesised an isocyanide-based multicomponent reaction (IMCR) and used as synthetic platforms to access bound-type polyheterocycles containing an epoxyisoindol-1(6)-one scaffold under green conditions. This rapid sonochemical synthetic strategy includes a double domino process using an orthogonal heterocyclic input in the Ugi-azide (UA) reaction. DFT calculations and NBO analysis were performed to understand the pseudopericyclic reaction involved in the 1,5-electrocyclization of the UA mechanism.
View Article and Find Full Text PDFA one-pot ultrasound-assisted regio and stereoselective synthesis of indenoquinoxaline engrafted spiropyrrolidines.
Org Biomol Chem
June 2024
Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
A catalyst free ultrasound-assisted regio-/stereoselective modular approach was accomplished for the synthesis of highly constrained indenoquinoxaline engrafted spiro pyrrolidines from easily available substrates. This one-pot strategy utilizes 1,3-dipolar cycloaddition from a four component reaction of ninhydrin, 1,2-phenylenediamine, β-nitrostyrene and benzylamine or amino acids under ultrasound irradiation. The transformation is mild and operationally simple, providing architecturally complex fused spiro polycyclic heterocycles.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!