15547-67-8

Basic information

• Product Name: 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline
• Synonyms: 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline
• CAS NO: 15547-67-8
• Molecular Weight: 295.338
• Mol File: 15547-67-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline(15547-67-8)
• EPA Substance Registry System: 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline(15547-67-8)

Safety Data

• Hazardous Substances Data: 15547-67-8(Hazardous Substances Data)

Upstream product

• 55580-65-9 6,7-dimethoxy-1-(4'-methoxyphenyl)-1,2,3,4-tetrahydrioisoquinoline 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1370593-48-8 C₂₅H₂₄O₄ 
• 1370593-37-5 4,5-dimethoxy-2-(3-phenylallyl)benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 100-07-2 4-methoxy-benzoyl chloride 
• 15547-66-7 N-(2-<3,4-dimethoxyphenyl>-ethyl)-p-methoxybenzamide 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 15462-83-6 6,7-dimethoxy-1-<(para-methoxy)phenyl>-3,4-dihydroisoquinoline 

Downstream Products

• 83287-02-9 menisporphine 

Relevant articles and documents

Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: Application to the synthesis of biologically active natural products

Herein, a simple and efficient method for the oxidative dehydrogenation (ODH) of tetrahydro-β-carbolines, indolines and tetrahydro-(iso)quinolines is described using a reusable, homogeneous cobalt-phthalocyanine photoredox catalyst in a biphasic medium. A biphasic system offers an advantage of easy separation of the product and an efficient reusability of the homogeneous photoredox catalyst. Also, the current system significantly helps to overcome the solubility issue of the substrate and catalyst at room temperature. Its potential applications to organic transformations are demonstrated by the synthesis of various biologically active N-heterocycles such as indoles, (iso)quinolines and β-carbolines and natural products such as eudistomin U, norharmane, and harmane and precursors to perlolyrine and flazin. Without isolation and purification, the catalyst solution can be reused up to 5 times with almost comparable reactivity. Furthermore, the efficiency of the reaction was demonstrated on a gram scale. To the best of our knowledge, this is the first report on ODH reactions using a non noble, reusable and homogeneous cobalt photoredox catalyst under environmentally friendly conditions.

Facile synthesis of substituted isoquinolines

A facile three-step protocol toward methoxy isoquinolines 7 starting with substituted 2-allylbenzaldehydes 9 was described. The overall synthetic process of skeleton 7 was carried out using the Grignard addition, PCC-oxidation, and one-pot oxidative cleavage of the olefinic group of skeleton 9 with OsO 4-NaIO4 followed by the condensation of the resulting 1,5-dicarbonyl compounds with NH4OAc. Skeleton 9 was prepared in high yield via the known Claisen rearrangement of skeleton 8 and O-methylation. Papaverine 2 is also synthesized via the simple three-step synthetic protocol.

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.