20435-01-2

Upstream product

• 874-90-8 4-methoxybenzonitrile 
• 58084-22-3 2-iodo-N-methyl-benzamide 
• 768-60-5 4-methoxyphenylacetylen 
• 145104-23-0 ortho-trimethylsilylmethyl-N-methylbenzamide 
• 2170-09-4 N,2-dimethylbenzamide 

Relevant academic research and scientific papers

Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones

A striking dependence on the method of workup has been found for annulation of benzonitriles ArCN to N-methyl 2-toluamide (1), facilitated by n-BuLi (2 equiv): Quenching the reaction by a slow addition of water produced the expected 1-isoquinolones 2; by

Palladium complexes with an annellated mesoionic carbene (MIC) ligand: Catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives

Two Pd(ii) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to a library of benzofuran, indole, isocoumarin and isoquinolone derivatives by the reaction of terminal alkynes with 2-iodo derivates of phenol, N-methyl aniline, benzoic acid and N-methyl benzamide, respectively. The general utility of the catalytic method is demonstrated using a variety of diversely substituted terminal alkynes and the corresponding desired products are obtained in good to excellent yields. On the basis of control experiments, a two-cycle mechanism is proposed which involves the Sonogashira coupling of 2-iodo derivatives with alkynes and the subsequent cyclization of the corresponding 2-alkynyl compounds.

Palladium-Catalyzed Synthesis of Isoquinolinones via Sequential Cyclization and N-O Bond Cleavage of N -Methoxy- o -alkynylbenzamides

A palladium-catalyzed controlled 6-endo-dig cyclization process has been developed for the chemoselective synthesis of isoquinolin-1-ones from N-alkoxy-o-alkynylbenzamides. The mechanism and scope of the reaction have also been investigated. Deuterium-labeling studies were used to confirm the intramolecular 1,5-hydrogen shift as a key step in the transformation. Georg Thieme Verlag Stuttgart · New York.

Intramolecular Peterson olefination of ortho-trimethylsilylmethyl-N-acyl-N-alkylbenzamides. A new route to 2-alkyl-1(2H)isoquinolones

A variety of 2-alkyl-1(2H)isoquinolones has been efficiently synthesized by intramolecular Peterson olefination of ortho-trimethylsilylmethyl-N-acyl-N-alkylbenzamides.