1633007-86-9

Upstream product

• 170956-92-0 N-methyl-2-(2-phenylethynyl)aniline 
• 920-46-7 Methacryloyl chloride 
• 13141-38-3 2-phenylethynylaniline 
• 74-88-4 methyl iodide 
• 536-74-3 phenylacetylene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 1644341-59-2 C₁₉H₁₆N₄O₄⁽¹⁸⁾O 
• 1644341-60-5 C₁₉H₁₆N₄O₃⁽¹⁸⁾O₂ 
• 1644341-31-0 1,3-dimethyl-6-nitro-3-(nitromethyl)-4-phenyl-3,5-dihydropyrrolo[4,3,2-de]quinolin-2(1H)-one 

Relevant academic research and scientific papers

Photocatalytic decarboxylative [2 + 2 + m] cyclization of 1,7-enynes mediated by tricyclohexylphosphine and potassium iodide

A novel photocatalytic decarboxylative [2 + 2 + m] cyclization of 1,7-enynes with alkyl N-hydroxyphthalimide (NHP) esters, using tricyclohexylphosphine and potassium iodide as redox catalysts, is reported for the construction of functional polycyclic compounds. This protocol tolerates primary, secondary, and tertiary alkyl NHP esters through a single reaction via decarbonylation, radical addition, C-H functionalization, and cyclization under mild conditions.

Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused γ-Lactones fromN-(o-Ethynylaryl)acrylamides and Formamide

An ultrafast (10 s) methodology to construct novel highly functionalized 2-quinolinones fromN-(o-ethynylaryl)acrylamides (1,7-enynes) is described for the first time. Microwave irradiation enabled the ultrafast synthesis of 2-quinolinone-fused γ-lactones from Fenton’s reagents in formamide. After six key consecutive reactions, including a diastereoselective step, 2-quinolinone-fused γ-lactones were obtained in good overall yield (up to 46%; 10 s).

Nickel-catalyzed cyclization of 1,7-enynes for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones

We herein described a nickel-catalyzed cyclization ofN-(o-ethynylaryl)acrylamides for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones. The two varied products could be easily obtained by tuning the reaction temperature. This reaction features easy temperature-control, high efficiency, and gram-scale synthesis.

Visible-Light-Mediated [2+2+1] Carbocyclization Reactions of 1,7-Enynes with Bromofluoroacetate to Form Fused Monofluorinated Cyclopenta[ c]quinolin-4-ones

Herein, we describe a new protocol for photoinduced radical [2+2+1] carbocyclization reactions of 1,7-enynes with bromofluoroacetate. These reactions, which proceed via a cascade involving fluoroalkylation, 6-exo-dig and 5-endo-trig cyclizations, H-transf

Cobalt-Catalyzed Enantioselective Hydroboration/Cyclization of 1,7-Enynes: Asymmetric Synthesis of Chiral Quinolinones Containing Quaternary Stereogenic Centers

An asymmetric cobalt-catalyzed hydroboration/cyclization of 1,7-enynes to synthesize chiral six-membered N-heterocyclic compounds was developed. A variety of aniline-tethered 1,7-enynes react with pinacolborane to afford the corresponding chiral boryl-fun

Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7-Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N-(Acyloxy)phthalimides as Radical Source

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Copper-catalyzed trifluoromethylazidation and rearrangement of aniline-linked 1,7-enynes: Access to CF3-substituted azaspirocyclic dihydroquinolin-2-ones and furoindolines

A set of reactions involving copper-catalyzed trifluoromethylazidation and then rearrangement of aniline-linked 1,7-enynes with the relatively poorly reactive Togni reagent I and TMSN3 was developed, and provided facile access to structurally d

Palladium-Catalyzed Construction of Tetracyclic Scaffolds via the 1,7-Enyne Carbocyclization/Iodophenol Dearomatization Cascade

An efficient palladium-catalyzed dearomatizing [2+2+1] carbocyclization of 1,7-enynes with iodophenols has been developed. A type of tetracyclic scaffold was built in this reaction, exhibiting a broad substrate scope with moderate to excellent yields. More importantly, this method provides a potential strategy for the synthesis of tetracyclic skeleton natural products.

Transition-Metal Controlled Diastereodivergent Radical Cyclization/Azidation Cascade of 1,7-Enynes

A strategy for achieving diastereodivergent azidations of enynes has been developed, employing azide transfer from the M-N3 complex to alkyl radicals. Following this concept, the diastereoselectivity has been switched by modulating the transition metals and the ligands. The Mn(III)-mediated radical cyclization/azidation cascade of 1,7-enynes afforded trans-fused pyrrolo[3,4-c]quinolinones, whereas the Cu(II)/bipyridine system gave cis-products.