24243-44-5

Basic information

• Product Name: 9H-Pyrido[3,4-b]indole, 1-(4-nitrophenyl)-
• CAS NO: 24243-44-5
• Molecular Formula: C17H11N3O2
• Molecular Weight: 289.293
• Mol File: 24243-44-5.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 9H-Pyrido[3,4-b]indole, 1-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Pyrido[3,4-b]indole, 1-(4-nitrophenyl)-(24243-44-5)
• EPA Substance Registry System: 9H-Pyrido[3,4-b]indole, 1-(4-nitrophenyl)-(24243-44-5)

Safety Data

• Hazardous Substances Data: 24243-44-5(Hazardous Substances Data)

Upstream product

• 3380-77-6 rac-1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride 
• 61-54-1 tryptamine 
• 555-16-8 4-nitrobenzaldehdye 
• 209169-31-3 1-(4-nitro-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 139655-04-2 (±)-2,3,4,9-tetrahydro-1-(4-nitrophenyl)-1H-pyrido[3,4-b]indole 
• 139655-01-9 tryptamine 
• 54-12-6 Trp 
• 74620-48-7 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid 

Downstream Products

• 771533-61-0 4-(9H-pyrido[3,4-b]indol-1-yl)aniline 
• 1381771-01-2 N-(4-(9H-pyrido[3,4-b]indol-1-yl)phenyl)thiophene-2-carboxamide 

Relevant articles and documents

A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air

A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.

Metal free one pot synthesis of Β-carbolines via a domino Pictet-Spengler reaction and aromatization

A convenient and efficient metal free, atom economical flexible synthesis of β-carbolines involving a domino Pictet-Spengler reaction and aromatization in oxygen atmosphere in N-methyl-2-pyrollidone (NMP) is described. Variety of aryl, heteroaryl and aliphatic aldehydes were found to be good substrates for this methodology. Several β-carbolines (6a-6t) and β-carboline methyl esters (7a-7e) were synthesized using this methodology.The same reaction carried out in argon atmosphere in the presence of catalytic amount of acid in NMP furnished, tetrahydro-β-carbolines (4a-4g).

Synthesis of β-carbolines via a silver-mediated oxidation of tetrahydro-β-carbolines

The oxidation of tetrahydro-β-carbolines to β-carbolines using silver carbonate was developed as an alternative to current methods. The oxidation is extremely mild and provides the products in modest to good yields after purification. A number of functional groups are tolerated by this methodology, including reduction-sensitive groups which are often cleaved with other methods. Though the mechanism is not fully understood, the reaction proceeds in an open flask, is not sensitive to light or moisture, and provides a viable synthetic route to compounds that are not easily prepared via other methodologies.