245122-59-2

Upstream product

• 25187-00-2 2-iodobenzophenone 
• 693-02-7 hex-1-yne 
• 13047-06-8 o-bromobenzophenone 
• 88-67-5 2-Iodobenzoic acid 
• 71-43-2 benzene 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Domino N2-Extrusion-Cyclization of Alkynylarylketone Derivatives for the Synthesis of Indoloquinolines and Carbocycle-Fused Quinolines

New synthetic approaches for the synthesis of indoloquinolines and carbocycle-fused quinolines have been developed employing alkynylketone substrates. These synthetic transformations involved the application of N2-extrusion of azido complexes as a key step to generate carbodiimidium ion and nitrilium ion in situ, which further cyclized intramolecularly with alkyne via a domino process to provide indoloquinolines and carbocycle-fused quinolines, respectively, in moderate to good yields.

Iodine-Mediated Cyclization of ortho-Alkynylaryl Ketones for the Synthesis of Indenone Derivatives

A new method for the synthesis of indenone derivatives based on the I2-promoted cyclization of ortho-alkynylaryl ketones has been developed. This method provides a metal-free and convenient route for the regioselective synthesis of indenones using ortho-alkynylaryl ketones with predefined substituents to give indenone products in moderate to good yields.

Silver-Catalyzed Cyclization of ortho-Carbonylarylacetylenols for the Synthesis of Dihydronaphthofurans

ortho-Carbonylarylacetylenols have been employed for the synthesis of dihydronaphthofurans via AgTFA-catalyzed annulation reaction. A broad range of substrates both ortho-keto- and ortho-formylarylacetylenols could be employed in this transformation providing the desired products in good yields. However, the reaction pathways of these two substrates are different. The reaction of the ketone precursors could directly lead to the desired products in a single operation while the reaction of the aldehyde precursors required a one-pot two-step approach, without isolation of the bicyclic acetal intermediates. In addition, this method was also successfully used for the synthesis of dihydronaphthopyrans in very good yields.

Asymmetric Hydrogenation of In Situ Generated Isochromenylium Intermediates by Copper/Ruthenium Tandem Catalysis

The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting of Cu(OTf)2 and a chiral cationic ruthenium–diamine complex. A range of chiral 1H-isochromenes were obtained in high yields with good to excellent enantioselectivity. These chiral 1H-isochromenes could be easily transformed into isochromanes, which represent an important structural motif in natural products and biologically active compounds. The chiral induction was rationalized by density functional theory calculations.

Copper-catalyzed cascade cyclization of 1,5-enynes: Via consecutive trifluoromethylazidation/diazidation and click reaction: Self-assembly of triazole fused isoindolines

Copper-catalyzed cascade cyclization of 1,5-enynes with two types of hypervalent reagents was developed via consecutive trifluoromethylazidation/diazidation and intramolecular click reaction (CUAAC), providing one-pot self-assembly of triazole fused isoindolines bearing a trifluoromethyl or an azide moiety. Moreover, the construction of a trifluoromethylcyclopropyl unit, which has been considered as a metabolically stable replacement for a tert-butyl moiety and was difficult to access, was also achieved under trifluoromethylazidation conditions. All these reactions exhibited excellent chemoselectivity, good to excellent yields and broad functional group tolerance.

The first formation of (1Z)-1-alkylidene-1H-isobenzofuranium amides and 1H-inden-1-ones: Acid-promoted 5-exo cyclization and hydration/aldol condensation reactions of o-ethynylbenzophenones

(1Z)-1-(2,2-Dimethylpropylidene)-1H-isobenzofuranium bis(trifluoromethylsulfonyl)amides were synthesized through 5-exo cyclization reactions between sterically encumbered o-alkynylbenzophenones and bis(trifluoromethylsulfonyl)imide (Tf2NH). It

The First Formation of (1Z)-1-Alkylidene-1H-isobenzofuranium Amides and 1H-Inden-1-ones: Acid-Promoted 5-exo Cyclization and Hydration/Aldol Condensation Reactions of o-Ethynylbenzophenones

(1Z)-1-(2,2-Dimethylpropylidene)-1H-isobenzofuranium bis(trifluoromethylsulfonyl)amides were synthesized through 5-exo cyclization reactions between sterically encumbered o-alkynylbenzophenones and bis(trifluoromethylsulfonyl)imide (Tf2NH). It

Coupling of β-cyanocarbene-chromium complexes with 2-alkynylbenzoyl derivatives: A [5+5]-cycloaddition approach to phenanthridines

The coupling of β-cyanocarbene complexes and 2-alkynylbenzoyl derivatives has been examined. The reaction afforded phenanthridine derivatives in a complex tandem process involving carbene-alkyne coupling, isobenzofuran formation, intramolecular Diels-Alder reaction using a nitrile dienophile, and deoxygenation. The chemistry could not be reproduced in non-chromium-based systems. Georg Thieme Verlag Stuttgart.

The reaction of o-alkynylarene and heteroarene carboxaldehyde derivatives with iodonium ions and nucleophiles: A versatile and regioselective synthesis of 1H-isochromene, naphthalene, indole, benzofuran, and benzothiophene compounds

The reaction of o-alkynyl-benzaldehydes 1 with different alcohols, silylated nucleophiles 5, electronrich arenes 10, and heteroarenes 12 in the presence of the reagent IPy2BF4, at room temperature, gave functionalized 4-iodo-1H-isochromenes 2, 6, 11, and 13 in a regioselective manner. When alkynes 16 and alkenes 19 and 20 were used as nucleophiles, a regioselective benzannulation reaction took place to form 1-iodonaphthalenes 17 and 1-naphthyl ketones 18, respectively. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives (23, 27, and 28, respectively). The three patterns of reactivity observed for the o-alkynylbenzaldehyde derivatives with IPy2BF 4 stem from a common iodinated isobenzopyrylium ion intermediate, A, that evolves in a different way depending on the nucleophile present in the reac-tion medium. A mechanism is proposed and the different reaction pathways observed as a function of the type of nucleophile are discussed. Furthermore, the reaction of the o-hexynyl-benzaldehyde 1b with styrene was monitored by NMR spectroscopy. Compound III, a resting state for the common intermediate in the absence of acid, has been isolated. Its evolution in acid media has been also tested, thereby providing support to the proposed mechanism.

Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives

(equation presented) The coupling of o-alkynylbenzoyl derivatives with carbene complexes has been investigated. The reaction initially affords isobenzofuran derivatives, which convert to alkylidenephthalan derivatives or can be trapped by various dienophi