Indolizidine and quinolizidine derivatives are readily assembled from proline or pipecolic acid and γ-nitroaldehydes by means of a decarboxylative annulation process. These reactions are promoted by simple acetic acid and involve azomethine ylides as reactive intermediates. The method was applied to the synthesis of an epiquinamide analog.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5013532 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.6b02020 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electro-catalyzed, solvent-controlled divergent decarboxylative annulation and hydroaminomethylation of cyclic aldimines with -arylglycines.
Chem Commun (Camb)
January 2025
Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, China.
Herein, we reported a sustainable and simple method involving electrochemical-catalyzed decarboxylative annulation and hydroaminomethylation of cyclic aldimines with -arylglycines by switching the reaction solvents. When the reaction was carried out in MeCN/HO or HO, the resulting products included imidazolidine-fused sulfamidates and C4-aminomethylated cyclic aldimines, obtained in moderate to good yields, respectively. Mechanistically, a radical pathway was proposed to be involved in this approach.
View Article and Find Full Text PDFVisible-light-induced decarboxylative cyclization.
Org Biomol Chem
December 2024
Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, India.
The application of visible light as an energy source provides a new avenue in organic transformation due to its mildness, efficiency and selectivity. In fact, recent years have witnessed remarkable advances in photoinduced decarboxylative coupling reactions involving carboxylic acids and their derivatives. Under appropriate photoredox conditions they undergo single electron transfer (SET), resulting in reactive radicals which can assemble with suitable reaction partners.
View Article and Find Full Text PDFNi-catalyzed asymmetric decarboxylation for the construction of carbocycles with contiguous quaternary carbon stereocenters.
Chem Sci
January 2025
Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University Yanxiang Road 99 Xi'an 710045 China
The first Ni-catalyzed asymmetric decarboxylative strategy for the construction of carbocycles with contiguous quaternary all-carbon stereocenters is reported. The key to the success of these reactions is the utilization of rationally designed allenylic methylene cyclic carbonates as substrates with Ni catalysis. The floppy allenylic group exerts unique electronic properties on the carbonate, which allows further asymmetric nucleophilic annulations with alkenes.
View Article and Find Full Text PDFRu-Catalyzed C-H Alkylation of 4-Aryl-pyrrolo[2,3-]pyrimidines with Diazo Compounds: An Access to Fluorescent Fused Heteroarenes.
J Org Chem
December 2024
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
A Ru(II)-catalyzed migratory insertion of carbene into C-H bonds of 4-aryl-pyrrolo[2,3-]pyrimidines has been developed. This transformation endows the facile fabrication of C-C bonds with high atom economy, good regioselectivity, and wide functional group tolerance, exploiting the directing properties of pyrimidinic nitrogen. In addition, the planar polycyclic pyrrolo-pyrimido-isoindole framework has been accomplished from a cascade reaction of bromination, cyclization, and decarboxylation of synthesized products.
View Article and Find Full Text PDFAg-Catalyzed Domino Decarboxylative Alkylation/Dearomative Annulation: Entry to Fused-Pyrido[4,3-]Indolones.
Org Lett
October 2024
Department of Analytical & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Here we report the development of unprecedented silver-catalyzed intramolecular annulations of -acrolyl-2-(3-indolyl) benzimidazoles with alkyl carboxylic acids to construct complex fused-pentacyclic alkaloid scaffolds. Divergent reactivities are noticed with altered groups at C2-indole of the substrate. The reaction proceeds through decarboxylative alkylation, followed by dearomative annulation in a domino manner with excellent diastereoselectivity.
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!