Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from γ,δ-unsaturated -arylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common -hydrazonyl radical, which evolves through a domino carboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangement to afford diverse tetrahydropyridazines. All reactions are carried out in very mild conditions, and the quite inexpensive [Ru(bpy)]Cl is used as the catalyst. Preliminary mechanism studies are presented, among them luminescence and electrochemical characterization of the involved species. Computational studies allow to rationalize the mechanism in accord with the experimental findings.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.0c02605 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Palladium-catalyzed asymmetric carbene coupling en route to inherently chiral heptagon-containing polyarenes.
Nat Commun
April 2024
College of Chemistry and Chemical Engineering, Qingdao University, Qingdao, 266071, China.
Developing facile and direct synthesis routes for enantioselective construction of cyclic π-conjugated molecules is crucial. However, originate chirality from the distorted structure around heptagon-containing polyarenes is largely overlooked, the enantioselective construction of all-carbon heptagon-containing polyarenes remains a challenge. Herein, we present a highly enantioselective synthesis route for fabricating all carbon heptagon-containing polyarenes via palladium-catalyzed carbene-based cross-coupling of benzyl bromides and N-arylsulfonylhydrazones.
View Article and Find Full Text PDFNovel Arylsulfonylhydrazones as Breast Anticancer Agents Discovered by Quantitative Structure-Activity Relationships.
Molecules
February 2023
Faculty of Pharmacy, Medical University of Sofia, 1000 Sofia, Bulgaria.
Breast cancer (BC) is the second leading cause of cancer death in women, with more than 600,000 deaths annually. Despite the progress that has been made in early diagnosis and treatment of this disease, there is still a significant need for more effective drugs with fewer side effects. In the present study, we derive QSAR models with good predictive ability based on data from the literature and reveal the relationships between the chemical structures of a set of arylsulfonylhydrazones and their anticancer activity on human ER+ breast adenocarcinoma and triple-negative breast (TNBC) adenocarcinoma.
View Article and Find Full Text PDFCatalytic Synthesis of 1-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers.
J Am Chem Soc
December 2021
Homogeneous, Supramolecular and Bio-Inspired Catalysis (HomKat) group, Van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
The metallo-radical activation of -allylcarbonyl-aryl -arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [Co(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds.
View Article and Find Full Text PDFVisible Light Mediated Photocatalytic -Radical Cascade Reactivity of γ,δ-Unsaturated -Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines.
J Org Chem
February 2021
Department of Chemistry, University of Torino, Via Pietro Giuria, 7-10125 Torino, Italy.
Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from γ,δ-unsaturated -arylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common -hydrazonyl radical, which evolves through a domino carboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangement to afford diverse tetrahydropyridazines.
View Article and Find Full Text PDFDirect Synthesis of Propen-2-yl Sulfones through Cascade Reactions Using Calcium Carbide as an Alkyne Source.
Org Lett
July 2020
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. China.
A simple method for the construction of propen-2-yl sulfones through cascade reactions of calcium carbide with arylsulfonylhydrazones using copper as a mediator is described. The salient features of this protocol are the use of readily available and easy-to-handle alkyne source, broad substrate scope, open-air condition, and simple operation procedure.
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!