132233-84-2

Upstream product

• 35849-09-3 o-bromobenzaldehyde dimethyl acetal 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 52753-91-0 (E)-methyl 3-(2-formylphenyl)acrylate 
• 164254-18-6 Ethyl 2-diazo-3-(2-(dimethoxymethyl)phenyl)-3-hydroxypropionate 
• 445425-72-9 [1-(2-Dimethoxymethyl-phenyl)-meth-(E)-ylidene]-prop-2-ynyl-amine 
• 1092845-19-6 1-(2-(dimethoxymethyl)phenyl)-4-methylpent-4-en-2-yn-1-ol 
• 1229972-20-6 1-(2-(dimethoxymethyl)phenyl)but-2-ynyl acetate 
• 87656-32-4 (2-(dimethoxymethyl)phenyl)methanol 
• 164254-39-1 Ethyl 2-diazo-3-(2-(dimethoxymethyl)phenyl)-3-oxopropionate 
• 164254-15-3 Ethyl 2-diazo-3-(2-formylphenyl)-3-oxopropionate 
• 357979-89-6 2-iodo-N-{2-[(1-naphthalen-1-yl-ethylamino)-methyl]-benzyl}-N-propa-1,2-dienyl-benzamide 

Relevant academic research and scientific papers

Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers

The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.

HETEROCYCLIC SPIRO-COMPOUNDS AS AM2 RECEPTOR INHIBITORS

Disclosed are compounds of the formula (I) and pharmaceutically acceptable salts thereof: wherein R1, R2, R4, R5, R6, R7, R8, R9, R10,Z, X1, X2, X3, L2, HET, n and q are as defined herein. The compounds are inhibitors of adrenomedullin receptor subtype 2 (AM2). Also disclosed are the compounds for use in the treatment of diseases modulated AM2, including proliferative diseases such as cancer; pharmaceutical compositions comprising the compounds; methods for preparing the compounds; and intermediates useful in the preparation of the compounds.

Copper-Catalyzed Radical Cascade Difluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes: A Route to Difluoromethylated Naphthoquinones

A novel copper-catalyzed cascade difluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes has been developed. This method affords an efficient and straightforward access to structurally diverse difluoromethylated naphthoquinones in one pot, starting from readily available starting materials. The reaction represents the first trans-acyldifluoromethylation of internal alkynes, which features aldehydes as acceptors for the addition of alkenyl radicals. Furthermore, this protocol can also access to monofluoromethylated naphthoquinone and difluoromethylated indanones in the same reaction condition.

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes

A novel copper-catalyzed cascade trifluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes is described, allowing a direct access to structurally diverse trifluoromethylated naphthoquinones under mild reaction conditions. It represents the first trans-acyltrifluoromethylation of internal alkynes.

Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals

Selective gold(I)-catalyzed rearrangement of aromatic methoxypropynyl acetals leads to fused catechol ethers (1,2-dialkoxynapthalenes) in excellent yields. Furthermore, this process extends to the analogous heterocyclic and aliphatic substrates. Alkyne activation triggers nucleophilic addition of the acetal oxygen that leads to an equilibrating mixture of oxonium ions of similar stability. This mixture is "kinetically self-sorted" via a highly exothermic cyclization. Selective formation of 1,2-dialkoxy naphthalenes originates from chemoselective aromatization of the cyclic intermediate via 1,4-elimination of methanol.

Combining Traceless Directing Groups with Hybridization Control of Radical Reactivity: From Skipped Enynes to Defect-Free Hexagonal Frameworks

This work discloses the first general solution for converting oligoalkynes into polyaromatic polycyclic systems free of pentagonal defects. The efficiency and selectivity of this cascade originate from the combination of the Bu3Sn-mediated TDG

Enantioselective intramolecular propargylic amination using chiral copper-pybox complexes as catalysts

Intramolecular propargylic amination of propargylic acetates bearing an amino group at the suitable position in the presence of chiral copper-pybox complexes proceeds enantioselectively to give optically active 1-ethynyl-isoindolines (up to 98% ee). The method described in this communication provides a useful synthetic approach to the enantioselective preparation of nitrogen containing heterocyclic compounds with an ethynyl group at the α-position. This journal is the Partner Organisations 2014.

Environmentally benign synthesis of indeno[1,2-b]quinolines via an intramolecular povarov reaction

A new synthetic route to indeno[1,2-b]quinolines via reactions of o-propargylbenzaldehydes with N-aryl amines based on an intramolecular aza-Diels-Alder (Povarov) reaction has been developed. This method offers several advantages such as no requirement fo

Lewis acid catalyzed intramolecular condensation of ynol ether-acetals. synthesis of alkoxycycloalkene carboxylates

Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.