67496-29-1

Usage

Molecular structure

Substituted benzene derivative with a bromine atom, an amino group, and a methylenedioxy group

Functional groups

Bromine atom, amino group, and methylenedioxy group

Application

Used in organic synthesis and medicinal chemistry research

Potential use

Building block for drug molecules

Utilization

Synthesis of pharmaceuticals and agrochemicals

Importance

Valuable intermediate in the production of complex organic molecules

Field of study

Organic chemistry

Upstream product

• 65417-74-5 2-bromo-4,5-(methylenedioxy)benzaldehyde oxime 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 120-57-0 piperonal 
• 2620-49-7 3,4-methylenedioxybenzylamine hydrochloride 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 

Downstream Products

• 420086-61-9 N-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-2-chloro-N-cyclohex-1-enyl-acetamide 
• 420086-62-0 dithiocarbonic acid S-{[(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-cyclohex-1-enyl-carbamoyl]-methyl} ester O-ethyl ester 
• 1070894-11-9 benzyl (6-bromobenzo[d][1,3]dioxol-5-ylmethyl)carbamate 
• 1255516-37-0 6-(4-fluorophenyl)-[1,3]dioxolo[4,5-g]quinazoline 
• 1101868-64-7 6-phenyl-[1,3]dioxolo[4,5-g]quinazoline 
• 1255516-36-9 6,7-methylenedioxy-2-(4-methylphenyl)quinazoline 
• 1399327-91-3 6,7-methylenedioxy-2-(4-chlorophenyl)quinazoline 
• 52886-06-3 hippadine 
• 18034-03-2 nornitidine 
• 226570-99-6 N-(6-bromo-3,4-dimethoxybenzyl)-N-(cyclohex-1-enyl)-2,2,2-trichloroacetamide 

Relevant academic research and scientific papers

Multi-Photocatalyst Cascades: Merging Singlet Oxygen Photooxygenations with Photoredox Catalysis for the Synthesis of Alkaloid Frameworks

The development of photocascades that rapidly transform simple and readily accessible furan substrates into polycyclic alkaloid frameworks or erythrina natural products is described. Each of the sequences developed makes use of photocatalyzed energy transfer processes, which generate singlet oxygen, to set up the substrates for the second photocatalyzed reaction, wherein electron transfer generates carbon-centered radicals for the cyclizations that give the final complex frameworks. A chemical switch has been developed that can “switch off” one photocatalyst; thus, allowing a second photocatalyst to take over control of the sequence. As a corollary, this strategy represents the first time it has been possible to use multiple photocatalysts in photocascades, and, as such, it expands significantly the reactions that can be included in such cascades and the order in which they can be initiated.

Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines

A diverse array of isoquinolines and phenanthridines have been accessed by developing a two-step, one-pot method constituting regioselective palladium-catalyzed Kuwajima-Urabe α-arylation of silylenol ethers and acid-mediated deprotection, annulation, and aromatization. Structural diversity in the silylenol ethers leads to three different classes of isoquinolines and phenanthridines from which related natural products can be derived. The synthetic utility of this method by the quick assembly of the natural product trispheridine is also demonstrated.

Rapid and convergent assembly of natural benzo[c]phenanthridines by palladium/norbornene catalysis

A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation

Synthesis of pyrrolophenanthridine alkaloids based on C(sp3)-H and C(sp2)-H functionalization reactions

Assoanine, pratosine, hippadine, and dehydroanhydrolycorine belong to the pyrrolophenanthridine family of alkaloids, which are isolated from plants of the Amaryllidaceae species. Structurally, these alkaloids are characterized by a tetracyclic skeleton that contains a biaryl moiety and an indole core, and compounds belonging to this class have received considerable interest from researchers in a number of fields because of their biological properties and the challenges associated with their synthesis. Herein, a strategy for the total synthesis of these alkaloids by using C-H activation chemistry is described. The tetracyclic skeleton was constructed in a stepwise manner by C(sp 3)-H functionalization followed by a Catellani reaction, including C(sp2)-H functionalization. A one-pot reaction involving both C(sp3)-H and C(sp2)-H functionalization was also attempted. This newly developed strategy is suitable for the facile preparation of various analogues because it uses simple starting materials and does not require protecting groups.

A Suzuki cross-coupling and intramolecular aza-Michael addition reaction sequence towards the synthesis of 1,10b-epi-7-deoxypancratistatins and their cytotoxicity studies

The development of an efficient approach to the construction of a phenanthridone is described. The convergent strategy commences with the preparation of Suzuki cross-coupling reaction precursors, arylboronic acid 12 and α-iodo enone 19, from piperonylamine (9) and (-)-D-quinic acid (10), respectively. The coupling of 12 and 19 followed by a key intramolecular aza-Michael addition produced phenanthridone 21 featuring a cis-fused B-C ring junction. The syntheses of compounds 25 and 26, both of which are C-1 and C-10b epimers of the naturally occurring potent antitumor agent 7-deoxypancratistatin (2), from 21 are elaborated in detail in this paper. The cytotoxicities of 25 and 26 were evaluated against three different cancer cell lines. Compound 26 served as a moderate growth inhibitor of THP-1 monocytic cells (GI50 = 14.5 μg/mL). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

A highly efficient short total synthesis of (+)-γ-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite l

Catalytic asymmetric transformations with fine-tunable biphenol-based monodentate ligands

A library of new fine-tunable monodentate phosphite and phosphoramidite ligands based on chiral biphenol have been designed and developed. These monodentate phosphorus ligands have exhibited excellent enantioselectivity in the Pd-catalyzed asymmetric allylic alkylation and Rh-catalyzed asymmetric hydrogenation.

A short synthesis of γ-lycorane using Ni/AcOH mediated radical cyclisation

A short synthesis of (±)-γ-lycorane 6 is described using two different radical cyclisations. The key step is the formation of tetrahydroindolone 9 by a nickel-promoted 5-endo radical cyclisation. This is followed by a tributylstannane-mediated 6-endo ring closure to the tetracyclic lactam 10 which is readily reduced tb (±)-γ-lycorane 6.

Application of a stereospecific intramolecular allenylsilane imino ene reaction to enantioselective total synthesis of the 5,11- methanomorphanthridine class of Amaryllidaceae alkaloids

Enantioselective total syntheses of the pentacyclic 5,11- methanomorphanthridine Amaryllidaceae alkaloids (-)-montanine (1), (-)- coccinine (2), and (-)-pancracine (3) were accomplished using an intramolecular concerted pericyclic allenylsilane imino erie

PALLADIUM ASSISTED ORGANIC REACTIONS. VII. THE PREPARATION OF CYCLOPALLADATED PRIMARY AND SECONDARY BENZYLAMINES

A new method is described for the preparation of cyclopalladated benzylamines, involving the reaction of the ortho-bromobenzylamines with bis(dibenzylideneacetone)palladium(0).By using this method cyclopalladated complexes of simple primary and secondary benzylamines have been obtained for the first time.These complexes have been fully characterised as either the monomeric bromo(benzylamine-6-C,N)triphenylphosphinepalladium(II) derivatives or as the corresponding acetyl-acetonates. 1H and 13C NMR spectral data have been obtained and, in most cases, full assignments have been made.