Radical Cascade Annulation of Biphenyl Acrylamides to Dibenzoazepinones: Experimental and DFT Studies DOI

Raju Dupud,

Ramakrishnan Thushara,

Karthik Kumar Merugu

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(31)

Опубликована: Июнь 6, 2024

Abstract An efficient method for the conversion of biphenyl acrylamides to dibenzoazepinones with −SCF 3 incorporation is described. This operationally simple radical cascade reaction employs CAN as an oxidant and exhibits good functional group tolerance. Substrates featuring −OCH , −CH −Br or −Cl at para ‐position aromatic ring a preference ipso ‐cyclization due intervention DMSO in reaction. Density theory (DFT) calculations provide valuable insights into reaction's energetics product selectivity.

Язык: Английский

Cationic, [1,5]‐aryl migrations of propargyl benzyl ethers ¬– A stereospecific approach to E‐ and Z‐tetrasubstituted olefins DOI

Santu Sadhukhan,

Sindoori R. Nair,

Beeraiah Baire

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2234 - 2240

Опубликована: Март 23, 2024

Abstract Herein we report the discovery and development of first example a cationic [1,5]‐aryl migration reaction, through an unprecedented phenonium ions. This reaction does not require any acid, base, transition metal‐based catalyst or promoter, instead promoted by water activated NXS reagents. It provides highly diastereoselective rapid access to medicinally biologically important tetra‐substituted olefins (allyl alcohols). The involvement ipso ‐carbon, as well ion during this novel, was strongly supported isolation 2‐oxaspiro[5.5]undecane‐9‐ones. methodology is tolerable for wide range propargyl‐benzyl ethers, resulting in selective construction structurally divergent library mono‐halo‐tricarbon‐substituted alkenes. Synthetic application has also been demonstrated converting two isomeric‐iodo‐olefins respective E‐ Z ‐isomers tamoxifen stereospecific manner.

Язык: Английский

Процитировано

2
Triflic Acid-Mediated Condensation of Phthalimide with Diaryl Ethers as a Route to Spiro-Isoindolinones: Mechanistic Insights and Related Reactions DOI
Alexander M. Genaev, Georgy E. Salnikov, Konstantin Yu. Koltunov

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15931 - 15940

Опубликована: Окт. 15, 2024

Phthalimide and N-phenylphthalimide smoothly condense with di-p-tolyl ether in triflic acid (CF3SO3H, TfOH) to obtain the corresponding spiro[isoindoline-1,9′-xanthen]-3-ones. Structural analogs of phthalimide, such as phthalic anhydride 1,3-indandione (but not saccharin), show similar reactivity. In contrast, N-(tetrafluoropyridin-4-yl)phthalimide reacts DTE by an alternative pathway, yielding isobenzofuran dispiro derivative. The mechanistic aspects these reactions are discussed on basis situ NMR theoretical (DFT) studies, providing insights key intermediacy O,O-diprotonated forms starting compounds.

Язык: Английский

Процитировано

2
3-[N,N-Bis(sulfonyl)amino]isoxazolines with Spiro-Annulated or 1,2-Annulated Cyclooctane Rings Inhibit Reproduction of Tick-Borne Encephalitis, Yellow Fever, and West Nile Viruses DOI Open Access
Kseniya N. Sedenkova,

Artem S. Sazonov,

Dmitry A. Vasilenko

и другие.

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(13), С. 10758 - 10758

Опубликована: Июнь 28, 2023

Spirocyclic compounds containing heterocyclic moieties represent promising 3D scaffolds for modern drug design. In the search novel anti-flaviviral agents, we have obtained a series of 3-[N,N-bis(sulfonyl)amino]isoxazolines spiro-annulated cyclooctane rings and assessed their antiviral activity against tick-borne encephalitis (TBEV), yellow fever (YFV), West Nile (WNV) viruses. The structural analogs spirocyclic with single sulfonyl group or 1,2-annulated ring were also investigated. Almost all studied revealed TBEV WNV. most active was spiro-isoxazoline derivative p-nitrophenyl groups in part (EC50 2.0 ± 0.5 μM), while highest potency WNV found lipophilic substituents moiety, naphtyl being favorable one 1.3 μM). summary, two agents based on N,N-bis(sulfonyl)amino]isoxazoline proposed, this type demonstrated

Язык: Английский

Процитировано

5
A General and Highly Versatile Heterogeneous Pd‐Catalyzed Oxidative Aminocarbonylation of Alkynes with Aromatic and Aliphatic Amines DOI Creative Commons
Juan Camilo Arango‐Daza, Jose R. Cabrero‐Antonino, Rosa Adam

и другие.

ChemSusChem, Год журнала: 2024, Номер 17(13)

Опубликована: Май 2, 2024

An efficient heterogeneous catalytic system for the oxidative aminocarbonylation of alkynes and amines in presence CO/O

Язык: Английский

Процитировано

1
Radical Cascade Annulation of Biphenyl Acrylamides to Dibenzoazepinones: Experimental and DFT Studies DOI

Raju Dupud,

Ramakrishnan Thushara,

Karthik Kumar Merugu

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(31)

Опубликована: Июнь 6, 2024

Abstract An efficient method for the conversion of biphenyl acrylamides to dibenzoazepinones with −SCF 3 incorporation is described. This operationally simple radical cascade reaction employs CAN as an oxidant and exhibits good functional group tolerance. Substrates featuring −OCH , −CH −Br or −Cl at para ‐position aromatic ring a preference ipso ‐cyclization due intervention DMSO in reaction. Density theory (DFT) calculations provide valuable insights into reaction's energetics product selectivity.

Язык: Английский

Процитировано

1