91944-01-3

Basic information

• Product Name: 3-phenyl-9H-pyrido[3,4-b]indole
• Synonyms: 3-phenyl-9H-pyrido[3,4-b]indole
• CAS NO: 91944-01-3
• Molecular Weight: 244.296
• Mol File: 91944-01-3.mol

Chemical Properties

• CAS DataBase Reference: 3-phenyl-9H-pyrido[3,4-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-9H-pyrido[3,4-b]indole(91944-01-3)
• EPA Substance Registry System: 3-phenyl-9H-pyrido[3,4-b]indole(91944-01-3)

Safety Data

• Hazardous Substances Data: 91944-01-3(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 103457-58-5 1,4-Bis(dimethylamino)-3-phenyl-2-aza-1,3-butadien 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 1346156-90-8 1-benzyl-3-bromo-1H-indole-2-carbaldehyde 
• 126422-02-4 Ethyl 2-phenyl-β-carboline-4-carboxylate 
• 126421-91-8 5-phenyl-[1,2,4]triazine-3-carboxylic acid ethyl ester 
• 176327-46-1 N-(benzenesulfonyl)-3-iodoindole-2-carboxaldehyde 
• 536-74-3 phenylacetylene 
• 80360-14-1 3-iodo-1-phenylsulfonyl-1H-indole 
• 258497-56-2 3-(phenylethynyl)-1-(phenylsulfonyl)indole-2-carbaldehyde 
• 207803-30-3 1-indol-1-yl-2-(5-phenyl-[1,2,4]triazine-3-sulfonyl)-ethanone 
• 126422-14-8 2-Phenyl-β-carboline-4-carboxylic acid 

Relevant articles and documents

Catalytic Enolate Arylation with 3-Bromoindoles Allows the Formation of β-Carbolines

Synthesis of substituted β-carbolines was accomplished by utilizing the catalytic enolate arylation reaction of ketones in conjunction with several 3-bromoindole derivatives. Quenching of the arylation reaction in situ with an electrophile allowed ready i

Synthesis of β-carbolines from 2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles

2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles and 1-benzenesulfonyl-3-iodo-1H-indole-2-carbaldehyde give in satisfactory yields 1,3- and 3-substituted-β-carbolines, respectively, by combined palladium-catalyzed coupling with alk-1-ynes followed by 6-endo-dig

Inverse electron demand diels-alder reactions of indole. VI. A fully removable tether for intramolecular reactions with 1,2,4-triazines

The use of the fully removable β-sulfonoacetyl tether to link indole with 1,2,4-triazines allows for the preparation of β-carbolines unsubstituted at C1 and N9 via an intramolecular inverse electron demand Diels-Alder reaction. Mechanistic studies using 2- and 3-deuterated indole derivatives suggest involvement of a [1,5]-hydride shift following the cycloaddition and loss of N2 that precedes desulfination.

Indole as a Dienophile in Inverse Electron Demand Diels-Alder Reactions: Reactions with 1,2,4-Triazines and 1,2-Diazines

Indole reacts with 1,2,4-triazines in the absence of solvent or in the presence of limited amounts of solvent to produce β- or γ-carbolines, benzonaphthyridines, or the noncyclized 3-indoles.The combined yields of cycloadducts with tricarbalkoxytriazines exceeds 90 percent, with the production of γ-carbolines exceeding 80 percent.The regiochemistry of the adduct and the ratio of the products is determined mainly by electronic effects of the triazine substituents.Indole also ungergoes a cyclocondensation reaction with tetramethyl 1,2-diazine-3,4,5,6-tetracarboxylate to give trimethyl 5H-6-oxophenanthridine-2,3,4-tricarboxylate.

Process for producing β-carboline derivatives

β-carbolines of formula I STR1 can be prepared by reacting an indole of formula II: STR2 with an azabutadiene of formula III STR3 in the presence of an acid at 50°-200° C.