128368-43-4

Upstream product

• 2475-80-1 methyl 2-amino-5-methoxybenzoate 
• 75-16-1 methylmagnesium bromide 
• 104-94-9 4-methoxy-aniline 
• 23842-82-2 2-amino-5-methoxybenzonitrile 
• 32338-02-6 2-bromo-4-methoxyaniline 
• 23042-77-5 1-(2-amino-5-methoxy-phenyl)-ethanone 
• 89433-06-7 2-(2-amino-5-methoxyphenyl)propan-2-ol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1426832-63-4 C₁₅H₂₁NO₃ 
• 157496-75-8 tert-butyl (2-iodo-4-methoxyphenyl)carbamate 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 

Downstream Products

• 128368-44-5 (2-Isopropenyl-4-methoxy-phenyl)-carbamic acid methyl ester 
• 1208117-70-7 (4-methoxy-2-(prop-1-en-2-yl)phenyl)carbamoyl cyanide 
• 1208117-72-9 C₁₁H₁₅NO 
• 2731-01-3 (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole 
• 5342-23-4 6-methoxy-4-methyl-2-oxo-1H-quinoline 
• 62851-43-8 zidometacin 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 1601-18-9 indomethacin methyl ester 
• 6260-97-5 (4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone 
• 128368-45-6 [(2-Isopropenyl-4-methoxy-phenyl)-methoxycarbonyl-amino]-acetic acid methyl ester 
• 128368-46-7 [(2-Isopropenyl-4-methoxy-phenyl)-methoxycarbonyl-amino]-acetic acid 
• 675578-56-0 N-allyl-N-acetyl-2-isopropenyl-4-methoxyaniline 

Relevant academic research and scientific papers

Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source

We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Enantioselective Intramolecular Copper-Catalyzed Borylacylation

An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

Synthesis of (±)-esermethole via an intramolecular carbamoylketene-alkene [2+2] cycloaddition

A synthesis of (±)-esermethole (2), a synthetic precursor of physostigmine (1), has been accomplished by using an intramolecular carbamoylketene-alkene [2+2] cycloaddition followed by nitrone-mediated regioselective ring expansion for the construction of the basic carbon framework of 2 as the key steps.

Highly enantioselective intramolecular cyanoamidation: (+)-horsfiline, (-)-coerulescine, and (-)-esermethole

(Figure Presented) The first asymmetric cyanoamidation with synthetically useful enantioselectivlty (ee up to 99%) to produce 3,3-disubstltuted oxindoles Is reported. Palladium catalysts with chi ral phosphoramldite ligands activate the cyanoformamide C-CN bond, which is subsequently functionalized with a tethered alkene to give all-carbon quaternary stereocenters. The use of the N,N-(i-Pr)2 derivative of octahydro-MonoPhos allowed the production of oxindoles with high enantioselectivlties. Cyanoformamides bearing free N-H groups are now tolerated, potentially allowing protecting-group-free synthesis. Oxindole products of cyanoamidation are rapidly transformed into (+)-horsfiline, (-)-coerulescine, and (-)-esermethole.

Novel and facile route to (+)-physovenine via intramolecular [2+2]cycloaddition reaction

A formal total synthesis of (±)-physovenine 1 from 2-amino-5-methoxyacetophenone 2 via an intramolecular [2+2]cycloaddition reaction is described.