113975-92-1

Upstream product

• 91940-89-5 4,5-dimethoxy-2-methylbenzoyl chloride 
• 109-89-7 diethylamine 
• 55171-61-4 2-bromo-4,5-dimethoxybenzoyl chloride 
• 105875-33-0 2-bromo-N,N-diethyl-4,5-dimethoxy-benzamide 
• 74-88-4 methyl iodide 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 113976-02-6 2-(4,5-dimethoxy-2-methylphenyl)-1,3-dioxolane 
• 90359-76-5 N,N-diethyl-3,4-dimethoxy-2-(trimethylsilyl)-benzamide 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 70946-18-8 N,N-diethyl-3,4-dimethoxybenzamide 
• 7721-62-2 4,5-dimethoxy-2-methylbenzaldehyde 
• 20736-28-1 4,5-dimethoxy-2-methylbenzoic acid 
• 90359-81-2 N,N-diethyl-3,4-dimethoxy-6-methyl-2-(trimethylsilyl)benzamide 

Downstream Products

• 1202036-60-9 3-(4,5-dimethoxy-2-methoxymethoxymethylphenyl)-6,7-dimethoxy-2H-isoquinolin-1-one 
• 1248621-77-3 C₁₈H₁₇NO₃ 
• 1248621-74-0 C₁₉H₁₉NO₃ 
• 1272658-60-2 C₁₉H₁₉NO₅ 
• 1078723-29-1 3-[5-benzyloxy-4-methoxy-2-(2-methoxymethoxyethyl)phenyl]-6,7-dimethoxy-2H-isoquinolin-1-one 
• 898808-87-2 3-(4-benzyloxy-5-methoxy-2-methoxymethoxymethylphenyl)-6,7-dimethoxy-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

A Versatile Total Synthesis of Benzo[c]phenanthridine and Protoberberine Alkaloids Using Lithiated Toluamide-Benzonitrile Cycloaddition

A new versatile synthesis of benzo[c]phenanthridine and protoberberine alkaloids using lithiated toluamide-benzonitrile cycloaddition was carried out. The coupling reaction between benzonitrile 6 with o-toluamides (8a-c) afforded 3-arylisoquinolines (9a-c

Enantiospecific synthesis of (S)-(-)-8-oxoxylopinine

The enantiospecific synthesis of (S)-(-)-8-oxoxylopinine 1 was performed using a lateral metallation strategy, in which (S)-alaninol or (S)-phenylalaninol was applied as chiral auxiliary and building block. (4S)-3-(4,5-Dimethoxy-2-methylbenzoyl)-2,2,4-tri

First total synthesis of the phenolic 7,8-dihydro-8-oxoprotoberberine alkaloid, cerasonine

First total synthesis of the phenolic protoberberine, cerasonine, was accomplished through a coupling reaction between o-toluamide and benzonitrile. This key step provided the 3-arylisoquinoline which was then successfully converted to 7,8-dihydro-8-oxoprotoberberine through an intramolecular S N2 reaction.

Directed Ortho Metalation of N,N-Diethylbenzamides. Silicon Protection of Ortho Sites and the o-Methyl Group

New general methodology of value in aromatic chemistry based on silicon protection of preferred ortho metalation sites in benzamides and o-methyl groups in o-toluamides (1, 2, Scheme I) is described.According to these methodologies, routes (Scheme II and V) to 1,2,5-, 1,2,4,5-, and 1,2,3-substituted aromatics with a variety of functionalities and oxidation states have been developed (Tables I and II).These tactics are used for the synthesis of difficult to access halo (10a-b, Scheme III) and methyl (21,25, Scheme VI) heterocycles.Ipso bromodesilylation reactions with bromine lead regiospecifically to o-bromobenzamides (12a,c, 14, Scheme IV).Walk-around-the-ring metalation processes provide highly substituted aromatics 27, 28, 29, and 30 (Scheme VII); the X-ray structure of the hexasubstituted derivative 30 shows a significant puckering of the aromatic ring.Cesium fluoride induced carbodesilylation of o-silylbenzamides with benzaldehyde affords, after TsOH cyclization, phthalides (31a-c, Scheme VIII) and constitutes a neutral alternative to the directed ortho metalation approach. α- and α,α-silylated o-toluamides are used in fluoride-mediated carbodesilylation (34a,d, Scheme IX) and desilylative Peterson olefination (35, Scheme X) procedures, respectively.The utility of α-silylated o-toluamide for the synthesis of a tetralin (38, Scheme XI) via an o-quinodimethane species is given.