1226977-79-2

Upstream product

• 38846-64-9 2-ethynylbenzaldehyde 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 766-83-6 m-chlorophenylacetylene 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1226977-85-0 10-(3-chlorophenyl)-15bH-isoquino[2,1-a]pyrrolo[2,1-c]quinoxaline 
• 1138735-11-1 3-(3-chlorophenyl)isoquinoline 

Relevant academic research and scientific papers

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding β-aminophosphonates or PARP1-inhibitor analogues.

Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates

An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.

Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds

Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).

Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

Stereospecific Synthesis of (Z,Z)-Isobenzofurans via Radical-Enabled Cleavage of C(sp3)?C(sp3) and C(sp2)-Halogen Bonds

A novel radical-induced annulation/1,8-halosulfonylation of β-alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)?C(sp3) and C(sp2)-halogen bonds, from which 47 examples of sulfone-containing 1,3-dimethylene-substituted (Z,Z)-isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to proceed through the in-situ generation of arylsulfonyl radicals, followed by selective radical addition-cyclization and ring-opening of the cyclopropyl unit as well as C(sp2)-halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C?S, C?O and C-halogen bonds. (Figure presented.).

Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium

An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.

Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols

A metal-free [2+2] cycloaddition and 1,4-addition sequence induced by S-centered radicals has been achieved by treating benzene-linked allene-ynes with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) in a one-pot procedure. The reaction provides a greener and more practical access to functionalized cyclobuta[a]naphthalen-4-ols with valuable applications. More than 50 examples are demonstrated with excellent diastereoselectivity and chemical yields. The reaction pathway is proposed to proceed by the following steps:[2+2] cycloaddition, insertion of SO2, 1,4-addition, diazotization, and tautomerization.

Copper Catalyzed Enantioselective Alkylation of Pyrrole with β,γ-Unsaturated α-Ketoesters: Application to One-Pot Construction of the Seven-Membered Ring by Merging a Gold Catalysis

A highly enantioselective Friedel-Crafts alkylation of pyrrole to β,γ-unsaturated α-ketoesters was developed by virtue of a chiral copper complex, affording the alkylated derivatives of pyrrole with good yields and excellent enantioselectivities. Moreover, merging copper catalysis with gold catalysis realized a one-pot construction of the seven-membered ring to give annulated pyrroles with moderate to good yields and high enantiomeric excesses.

Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: A potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines

The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. The scope and limitation of this reaction are discussed. As an extension of this chemistry, N-tosylisoquinolinium imides, generated in situ from N′-(2-alkynylbenzylidene)-tosylhydrazides via an AgOTf-catalyzed 6-endo-dig electrophilic cyclization, readily undergo aryne [3 + 2] cycloaddition to afford indazolo[3,2-a]-isoquinolines in the same pot, offering a highly efficient route to these potential anticancer agents.

Facile assembly of fused isoquinolines by gold(i)-catalyzed coupling-cyclization reactions between o-alkynylbenzaldehydes and aromatic amines containing tethered nucleophiles

A gold(I)-catalyzed, operationally simple coupling-cyclization technique was developed for the synthesis of isoquinoline-fused polycyclic compounds. The reaction makes use of two coupling partners such as o-alkynylbenzaldehydes and aromatic amines having tethered nucleophiles. The reaction is easy to perform, broad in scope, and allows the generation of a number of biologically important heterocyclic motifs from readily accessible starting materials. A mechanism for the reaction is discussed.