Herein, we report the synthesis and characterization of a series of thioarylmaleimides and their varied propensity toward highly selective domino Diels-Alder (D-A)/rearrangement, D-A/ene/elimination, and D-A/oxidation reactions to give three types of thienyl-fused architectures. Stereochemical assignment was achieved using a combination of nuclear magnetic resonance (NMR) studies, gauge independent atomic orbital (GIAO) NMR chemical shift calculations, and DP4+ analysis. Transition-state calculations support an asynchronous concerted mechanism and provide support for rationalizing the observed regio- and stereoselectivity.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c01797 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Continuous flow synthesis of the antiviral drug tecovirimat and related sp-rich scaffolds.
Org Biomol Chem
October 2024
University College Dublin, School of Chemistry, Science Centre South, D04 N2E5 Dublin, Ireland.
Article Synopsis
- * The synthesis involves a high-temperature reaction between cycloheptatriene and maleic anhydride, creating an important scaffold that is needed for the drug.
- * The research also explores the interaction of an intermediate with various hydrazines, leading to different chemical structures that can be developed into drug-like compounds.
Triple Nucleophilic Head-to-Tail Cascade Polycyclization of Diazodienals via Combination Catalysis: Direct Access to Cyclopentane Fused Aza-Polycycles with Six-Contiguous Stereocenters.
JACS Au
June 2024
Department of Chemistry, Indian Institute of Science Education & Research Bhopal, Bhopal, Madhya Pradesh 462066, India.
Reported herein are the bench stable (24)-diazohexa-2,4-dienals (diazodienals) and their unprecedented polycyclization with aldimine and arylamines enabled by Rh(II)/Brønsted acid relay catalysis. This scalable and atom-economical reaction provides direct access to the biologically important azatricyclo[6.2.
View Article and Find Full Text PDFInterrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds.
J Org Chem
April 2024
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation.
Four heteroatoms dance in the cascade of four pericyclic reactions initiated by ozonolysis of C═N bonds. Switching from imines to semicarbazones introduces the fifth heteroatom that slows this dance, delays reaching the thermodynamically favorable escape path, and allows efficient interception of carbonyl oxides (Criegee intermediates, CIs) by an external nucleophile. The new three-component reaction of alcohols, ozone, and oximes/semicarbazones greatly facilitates synthetic access to monoperoxyacetals (alkoxyhydroperoxides).
View Article and Find Full Text PDFPericyclic Cascade Reactions Affording Thienyl- and Benzo[]thienyl-Fused Architectures: A Synthetic and Density Functional Theory Analysis of Asynchronous Diels-Alder Reactions of Thioarylmaleimides.
J Org Chem
February 2024
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick E3B 5A3, Canada.
Herein, we report the synthesis and characterization of a series of thioarylmaleimides and their varied propensity toward highly selective domino Diels-Alder (D-A)/rearrangement, D-A/ene/elimination, and D-A/oxidation reactions to give three types of thienyl-fused architectures. Stereochemical assignment was achieved using a combination of nuclear magnetic resonance (NMR) studies, gauge independent atomic orbital (GIAO) NMR chemical shift calculations, and DP4+ analysis. Transition-state calculations support an asynchronous concerted mechanism and provide support for rationalizing the observed regio- and stereoselectivity.
View Article and Find Full Text PDFA Modular Strategy for the Synthesis of Dothideopyrones E and F, Secondary Metabolites from an Endolichenic Fungus.
J Nat Prod
April 2023
Department of Chemistry, Faculty of Natural Sciences, Norwegian University of Science and Technology, NO-7491 Trondheim, Norway.
Endolichenic fungi are a rich source of natural products with a wide range of potent bioactivities. Herein, syntheses of the two naturally occurring α-pyrones dothideopyrone E and F are presented. These natural products were isolated from a culture of the endolichenic fungus sp.
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!