A5048522154- Catalytic Alkyne Reactions
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Cyclopropane Reaction Mechanisms
- Catalytic C–H Functionalization Methods
- Synthetic Organic Chemistry Methods
- Sulfur-Based Synthesis Techniques
- Crystallography and molecular interactions
- Synthesis and Catalytic Reactions
- Chemical synthesis and alkaloids
- Catalytic Cross-Coupling Reactions
- Click Chemistry and Applications
- Oxidative Organic Chemistry Reactions
- Radical Photochemical Reactions
- Cyclization and Aryne Chemistry
- Asymmetric Synthesis and Catalysis
- Catalysis and Hydrodesulfurization Studies
- Business Strategy and Innovation
- Organoselenium and organotellurium chemistry
- Asymmetric Hydrogenation and Catalysis
- Digital Platforms and Economics
- Advanced Synthetic Organic Chemistry
University of Toledo
2022-2024
Nanjing University
2021-2023
University of Hyderabad
2014-2021
Stable ynamides are used for the development of novel synthetic transformations and construction unusual carbo/heterocycles. The intramolecular cyclization π-tethered alkene/alkyne/allene-ynamides is studied extensively fabrication a wide range molecular scaffolds various applications. ketene-acetal/aminal generated in situ from participates cyclization/cycloisomerization processes to yield N-bearing fused heterocycles. This account summarizes scientific merits advances made...
A regioselective sulfonyl/sulfinyl migration cycloisomerization cascade of alkyne-tethered ynamides is developed in the presence XPhosgold catalyst. This reaction first example a general [1,3]-sulfonyl from nitrogen center to β-carbon atom ynamides, followed by umpolung 5-endo-dig cyclization ynamide α-carbon gold-activated alkyne, and final deaurative [1,5]-sulfinylation. process allows synthesis peripherally decorated unconventional 4-sulfinylated pyrroles with broad scope...
A novel synthetic route to benzo[f]dihydroisoquinolone through a p-TsOH promoted cascade cyclization of easily accessible diyne-tethered ynamides in the presence Au(I)-catalyst is described. This reaction unveils broad substrate scope, constructing wide range benzo[f]dihydroisoquinolones good yields. The are synthesized from inexpensive o-iodoaniline Sonogashira couplings and Cu-mediated C-N bond formation. role examined, pathway also deduced. benzo[f]isoquinoline scaffold constructed...
A novel and straightforward protocol is demonstrated for the synthesis of highly substituted oxazoles from readily accessible ynamides in presence ytterbium(III) trifluoromethanesulfonate [Yb(OTf)3], N-iodosuccinimide (NIS), acetonitrile. Multiple oxazole skeletons aryl periphery are constructed a single operation first time. The hydroamidation iodo-imidation to trisubstituted tetrasubstituted ketene aminals exemplified. An isotope labeling experiment used identify oxygen source this...
The enol-equivalent of an amide: a tool useful to construct novel N-heterocycles.
Regioselective hydration of the terminal halo-substituted propargyl carboxylate by gold(I) catalyst is reported. The mild catalytic conditions tolerate common acid-labile protecting groups, and a wide variety α-acyloxy α′-halo ketones are efficiently synthesized within short reaction time. used for synthesis 2-aminothiazoles.
An unprecedented metal-free dimethyl sulfoxide (DMSO) and N-iodosuccinimide mediated regioselective 5-exo-dig oxidative cyclization of an in situ generated enol equivalent amides from ynamides bearing internal alkynes is demonstrated. The reaction allows easy access to functionalized pyrrolidone skeletons. Pyrrolidones having 3-o-biaryl motifs successfully undergo intramolecular electrophilic with the α,β-unsaturated olefin, furnishing spiro-pyrrolidone motifs. A one-pot sequential...
An uncommon sulfur → selenium carbon radical transfer process is employed to develop an unprecedented selenyl radical-mediated regioselective cyclization of yne-tethered-ynamides.
Metal free α-halogenation of ynamides at room temperature.
Demonstrated herein is an AuI -catalyzed annulation of sulfonyl-protected ynamides with substituted 1,2-benzisoxazoles for the synthesis E-benzo[e][1,3]oxazine derivatives. The transformation involves addition benzisoxazole to gold-activated ynamide, ring expansion fragment provide α-imino vinylic gold intermediate, and 1,2-migration sulfonamide motif masked carbene center deliver respective ring-expanded benzo[e][1,3]oxazine predominant E configuration. A trapping experiment justifies...
This report outlines a versatile strategy for synthesizing diverse array of N-heterocycles. By the utilization common olefins, this simple protocol facilitates their coupling with various bifunctional reagents. Furthermore, it can be integrated C–H amination techniques to directly produce N-heterocycles in multicomponent cascade process. The unique bond disconnection logic employed process underscores its efficiency achieving rapid simplification through couplings.
Reported herein is a <italic>syn</italic>-thioallylation of ynamides incorporating sulfide moiety at the α-position and an allyl group β-position ynamide.
Abstract Presented herein is a gold(I) catalyzed intramolecular tetradehydro‐Diels‐Alder (TDDA) reaction of alkyne‐tethered‐ynamides for the construction structurally complex 2,3‐dihydrobenzo[ f ]indole derivatives. The mechanism regioselective benzannulation was rationalized by means density functional theory (DFT) calculations. Substrates having an aryl group at ynamide terminus are exclusively participating in this TDDA under gold catalysis.
Abstract A regioselective sulfonyl/sulfinyl migration cycloisomerization cascade of alkyne‐tethered ynamides is developed in the presence XPhosgold catalyst. This reaction first example a general [1,3]‐sulfonyl from nitrogen center to β‐carbon atom ynamides, followed by umpolung 5‐ endo ‐dig cyclization ynamide α‐carbon gold‐activated alkyne, and final deaurative [1,5]‐sulfinylation. process allows synthesis peripherally decorated unconventional 4‐sulfinylated pyrroles with broad scope...
Silver-catalyzed cyclization and cycloisomerization of ketene N,N-acetals at room temperature has been developed to access a variety highly substituted cyclobutene-fused azepine 1,2-dihydropyridine derivatives. This cost-effective method is reliably implemented for the gram-scale synthesis dihydropyridine The iodo group in periphery motif can be functionalized with both Suzuki Sonogashira reactions.
N-heterocycles are privileged pharmaceutical scaffolds in drug discovery and development.
Hypervalent iodine catalysis has been widely utilized in olefin functionalization reactions. Intermolecularly, the regioselective addition of two distinct nucleophiles across is a challenging process hypervalent catalysis. We introduce here unique strategy using simple lithium salts for catalyst activation. The activated allows intermolecular coupling soft such as amides onto electronically olefins with high regioselectivity.
Abstract The scalable title cyclization offers access to variously functionalized pyrrolidinone derivatives.
Abstract The reaction of acetoxy ynamide (IX) with CHI 3 furnishes the iodoacrylamide (XI) via an 1,3‐acetate shift.
Abstract Review: [12 refs.