83026-93-1

Upstream product

• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 108-86-1 bromobenzene 
• 100-58-3 phenylmagnesium bromide 
• 15981-63-2 2',3',5'-tri-O-acetylnebularine 
• 98-80-6 phenylboronic acid 
• 2004-06-0 6-Chloropurine riboside 
• 58-61-7 adenosine 
• 7387-57-7 triacetyladenosine 
• 591-50-4 iodobenzene 
• 5987-74-6 6-iodo-9-[β-(2',3',5'-tri-O-acetyl)-D-ribofuranosyl]purine 
• 71-43-2 benzene 

Downstream Products

• 1310063-73-0 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(2-acetoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 1310063-74-1 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(2,6-diacetoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 1416131-66-2 C₃₉H₄₁N₈O₁₀P 
• 1416131-65-1 C₁₈H₂₁N₄O₇P 
• 1379667-45-4 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-[6-{2-(4-methylphenylsulfonamido)phenyl}-9H-purin-9-yl]tetrahydrofuran-3,4-diyl diacetate 
• 1284287-16-6 6-([1,1'-biphenyl]-2-yl)-9-β-D-(2',3',5'-tri-O-acetyl)ribofuranosyl-9H-purine 
• 84765-98-0 6-phenyl-9-(β-D-ribofuranosyl)-9H-purine 

Relevant academic research and scientific papers

PdII-Catalyzed Purine-Directed Ortho Nitration of 6-Arylpurines by C(sp2)–H Activation: A Practical Approach to Synthesize 6-(2-Nitroaryl)-Purine Derivatives

Herein we report a method for PdII-catalyzed purine-directed ortho nitration of 6-arylpurines via C(sp2)–H activation by using tBuONO/O2 as nitration agent. This procedure is highly efficient and produces a range of 6-(2-nitroaryl)-purine derivatives with good chemoselectivity and functional-group tolerance. The utility of the method is further illustrated in the synthesis of antibacterial agent.

Silver-Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids

A practical and operationally simple protocol for the assembly of 6-aryl-substituted purines through the direct C6–H arylation of purines and 8-azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.

2-catalyzed directed N -Boc amidation of arenes "on water"

Rhodium(III) catalysis "on water" is effective for directed C-H amidation of arenes. The catalytic process is promoted by OH groups present on the hydrophobic water surface and is inefficient in all (most) common organic solvents investigated so far. In the presence of easily prepared tert-butyl 2,4-dinitrophenoxycarbamate, a new and stable nitrene source, the "on water" reaction can efficiently provide the desired N-Boc-aminated products with good functional group tolerance.

Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: Palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides [1]

A series of C-6 alkyl, cycloalkyl, and aryl-9-(β-d-ribofuranosyl) purines were synthesized and their substrate activities with Escherichia coli purine nucleoside phosphorylase (E. coli PNP) were evaluated. (Ph 3P)4Pd-mediated cross-c

Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation

We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N2 as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.

Microwave promoted palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of 6-chloropurines with sodium tetraarylborate in water

An efficient method for the synthesis of 6-arylpurines (nucleosides) was developed via Suzuki-Miyaura cross-coupling reactions of 6-chloropurines (nucleosides) and sodium tetraarylborate in neat water (ethanol). The process gave good to high isolated yiel

Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: Application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids

The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6- chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a se

The Suzuki-Miyaura cross-coupling reactions of 6-halopurines with boronic acids leading to 6-aryl- and 6-alkenylpurines

The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine with boronic acids gave 6-alkylated purines in moderate to excellent yields. The best results with electron rich arylboronic acids were obtained in toluene in the presence of anhydrous

Preparation and reactions of new zincated nitrogen-containing heterocycles

A range of nitrogen-containing iodinated or in some cases brominated heterocycles were converted to the corresponding zincated heterocyclic derivatives by the direct insertion of zinc dust under mild conditions (25°C to 70°C, 1-3 h) in a solvent like THF or DMAC. This reaction was extended to the preparation of zincated nucleic acid bases and nucleosides. The reaction of these new zinc reagents toward various electrophiles with palladium (O) or copper(I) catalysis allows the preparation of a broad range of polyfunctional nitrogen-containing heterocycles.