56666-88-7

Basic information

• Product Name: 4-Methoxy-β-carboline
• Synonyms: 4-Methoxy-9H-pyrido[3,4-b]indole;4-Methoxy-β-carboline
• CAS NO: 56666-88-7
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.22
• Mol File: 56666-88-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Methoxy-β-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-β-carboline(56666-88-7)
• EPA Substance Registry System: 4-Methoxy-β-carboline(56666-88-7)

Safety Data

• Hazardous Substances Data: 56666-88-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 98263-41-3 2-Benzamido-4-oxo-1,2,3,4-tetrahydro β-carboline 
• 137937-05-4 2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline 
• 77-76-9 2,2-dimethoxy-propane 
• 137937-00-9 9-benzyl-4-methoxy-β-carboline 
• 854545-80-5 2-(toluene-4-sulfonyl)-1,2,3,9-tetrahydro-β-carbolin-4-one 
• 854545-85-0 4-(2-amino-phenyl)-5-imino-1-(toluene-4-sulfonyl)-1,2,5,6-tetrahydro-pyridin-3-ol 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 17017-66-2 ethyl 1-benzyl-1H-indole-2-carboxylate 
• 81787-94-2 1-benzylindole-2-carbaldehyde 
• 137937-04-3 ethyl N-<(indol-2-yl)methyl>-N-formylaminoacetate 
• 137936-99-3 9-benzyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline 
• 137936-98-2 ethyl N-<(1-benzylindol-2-yl)methyl>-N-formylaminoacetate 
• 187264-03-5 (1-benzyl-1H-indol-2-yl)methanol 

Downstream Products

• 60807-25-2 4-methoxy-β-carboline-1-carboxylic acid methyl ester 

Relevant articles and documents

A new synthesis of 4-oxygenated β-carboline derivatives by Fischer indolization

A new and short synthetic route to the 4-methoxy-β-carboline skeleton is described. The route involves Fischer indolization of enehydrazine of 1-tosylpiperidine-3,5-dione and successive acetalization-elimination for aromatization of 1,2,3,4-tetrahydro-2-tosyl-9H-β-carbolin-4-one. This method is efficiently applicable to synthesis of the benzene-part substituted 4-oxygenated β-carboline derivatives.

Unexpected Debenzylation of N-Benzylindoles with Lithium Base. A New Method of N-Debenzylation

The reaction of N-benzylindoles with lithium base resulted in debenzylation.The key step would be generation of benzyl carbene from the preformed N-benzyl anion.This reaction should serve as a new debenzylation method for indoles and related compounds.

DDQ Oxidations in the Indole Area. Synthesis of 4-Alkoxy-β-carbolines Including the Natural Products Crenatine and 1-Methoxycanthin-6-one

The seven-step synthesis of the cytotoxic, antileukemic alkaloid 1-methoxycanthin-6-one (2b) is described.The pivotal steps are represented by the oxidation (DDQ, aqueous THF, room temperature) of 1-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline (10) to provide the 4-oxo-substituted derivative 14 in 78percent yield, and conversion of the 4-oxo analogue 7 into 4-methoxy-1-alkyl-β-carboline (23) via a methoxylation-oxidation process .This four-step, one-pot reaction has been shown to be general; 4-oxo-1,2,3,4-tetrahydro-β-carboline (18) was converted into the corresponding 4-methoxy-, 4-ethoxy-, 4-(allyloxy)-, and 4-(benzyloxy)-β-carbolines (19a-d, respectively) on heating in the appropriate alcohol in the presence of pTSA and a trialkyl orthoformate (Table II).The proposed mechanism for this intriguing transformation is outlined in Scheme IV.Execution of this process has also resulted in a four-step preparation of crenatine (1a), a 4-methoxy-1-ethyl-β-carboline alkaloid.Finally, steric and electronic parameters have also been successfully manipulated to direct the DDQ oxidation of 1,2,3,4-tetrahydro-β-carbolines to position 1, regiospecifically.The conversion of tetrahydro-β-carboline 25 into 2-acylindole 38 and benzamide 26 into 1-oxotetrahydro-β-carboline 27 (Table I), respectively, is in agreement with the proposed mechanism for this process.