29093-41-2

Usage

InChI:InChI=1/C15H15NO2/c1-9-6-11-12-7-10(17-2)4-5-13(12)16-14(11)8-15(9)18-3/h4-8,16H,1-3H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 98447-30-4 2-bromo-4-methoxy-1-nitrobenzene 
• 175883-62-2 4-methoxy-3-methylphenylboronic acid 
• 104-94-9 4-methoxy-aniline 
• 139102-34-4 methyl 4-bromo-2-methoxybenzoate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 137832-56-5 methyl 4-amino-5-iodo-2-methoxybenzoate 
• 36661-35-5 3-methoxy-N-(4-methoxyphenyl)-4-methylaniline 
• 87-64-9 2-chloro-6-methylphenol 
• 91506-05-7 5-bromo-1-chloro-2-methoxy-3-methylbenzene 
• 7530-27-0 4-bromo-2-chloro-6-methyl-phenol 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 133088-44-5 2-chloro-5-methoxy-4-methylaniline 
• 7206-70-4 4-amino-5-chloro-2-methoxybenzoic acid 

Downstream Products

• 51971-09-6 glycozolidal 

Relevant academic research and scientific papers

C-N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: Synthesis of carbazole alkaloids

Copper promoted N-arylation of methyl 4-amino-3-iodobenzoate with boronic acids followed by Pd-catalyzed intramolecular C-H arylation provides an efficient route to methyl carbazole-3-carboxylate derivatives. This methodology was implemented in the synthe

GLYCOZOLIDOL, AN ANTIBACTERIAL CARBAZOLE ALKALOID FROM GLYCOSMIS PENTAPHYLLA

Glycozolidol, a new carbazole alkaloid, has been isolated from the roots of Glycosmis pentaphylla.Its structure has been established as 6-hydroxy-2-methoxy-3-methylcarbazole on the basis of physical and chemical evidence.The compound has been found to be active against some Gram-positive and Gram-negative bacteria.Key Word Index - Glycosmis pentaphylla; Rutaceae; carbazole alkaloid; glycozolidol.

Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights

The evolution of a more reactive chiral vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Br?nsted or Lewis acid additive. The resultant vanadium complex is found to effect the asymmetric oxidative ortho-ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Experimental and quantum mechanical studies of the mechanism indicate that the additives aggregate the vanadium monomers. In addition, a singlet to triplet crossover is implicated prior to carbon-carbon bond formation. The two lowest energy diastereomeric transition states leading to the enantiomeric products differ substantially with the path to the minor enantiomer involving greater torsional strain between the two phenol moieties.

One-pot synthesis of carbazoles via tandem C-C cross-coupling and reductive amination

We have developed a highly efficient synthetic route to carbazoles that employs sequential C-C/C-N bond formation via Suzuki cross-coupling and Cadogan cyclization using commercially available or easily preparable starting materials. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products (glycozoline, glycozolicine, glycozolidine and clausenalene).

Synthesis of 2-hydroxy-7-methylcarbazole, glycozolicine, mukoline, mukolidine, sansoakamine, clausine-H, and clausine-K and structural revision of clausine-TY

A Buchwald-Hartwig amination and palladium(II)-catalyzed oxidative cyclization reaction sequence provided efficient access to a series of oxygenated tricyclic carbazoles. In the present work, this approach was applied to the total syntheses of the natural

Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine

A mild and. efficient methodology for the synthesis of oxygenated. carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The scope of the reaction was also expanded, to include the synthesis of benzo fused carbazolequinones. Wiley-VCH Verlag GmbH & Co. KGaA.

Transition metals in organic synthesis, part 91:1 palladium-catalyzed approach to 2,6-dioxygenated carbazole alkaloids - First total synthesis of the phytoalexin carbalexin C

The palladium(0)-catalyzed C-N bond formation and palladium(II)-catalyzed oxidative cyclization provide an efficient route to a series of 2,6-dioxygenated carbazole alkaloids including the first total synthesis of the phytoalexin carbalexin C.

N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation

(Chemical Equation Presented) N-H carbazoles can be produced from 2-chloroanilines and aryl bromides via consecutive catalytic amination and C-H activation. In many instances, this can be done in a tandem manner in one pot. The methodologies developed can be used in the synthesis of a range of carbazoles, including the natural products Clausine P and glycozolidine and a precursor in the synthesis of Clausines H, K, O, and 7-methoxy-O-methylmukonal, and can be extended to the synthesis of indoles.

A REGIOSPECIFIC SYNTHESIS OF CARBAZOLES VIA CONSECUTIVE PALLADIUM-CATALYZED CROSS-COUPLING AND ARYNE-MEDIATED CYCLIZATION

A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions.The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.

Thermal cyclisation of diphenylamine to carbazole: Synthesis of the natural product glycozolidine

Iodine-catalysed cyclisation at 350 °C of diphenylamine to carbazole has been used to synthesise glycozolidine (VI), a natural product from Glycosmis pentaphylla (Retz.) D.C.