92060-18-9

Upstream product

• 2142-70-3 2-iodoacetophenone 
• 100-63-0 phenylhydrazine 
• 926652-87-1 1-[1-(2-iodophenyl)ethylidene]-2-phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 796843-17-9 1-methyl-2-[2-(prop-1-ynyl)phenyl]-1H-indole 
• 796843-29-3 2-(2-ethynylphenyl)-1H-indole 
• 1239778-88-1 6-(4-chlorophenyl)indolo[1,2-c]quinazoline 
• 1385821-07-7 6-(4-methoxyphenyl)-indolo[1,2-c]quinazoline 
• 110423-27-3 6-phenyl-indolo[1,2-c]quinazoline 
• 1239778-99-4 6-(p-tolyl)indolo[1,2-c]quinazoline 
• 1224635-31-7 6-phenyl-11H-benzo[a]carbazole 

Relevant academic research and scientific papers

Scalable electrochemical synthesis of diaryliodonium salts

Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN-HFIP-TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.

Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with o-Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1- A[isoquinolines

A novel palladium-catalyzed cascade cyclization of alkene-tethered aryl halides with o-bromobenzoic acids is described, which provides an efficient avenue for building various fused hexacyclic scaffolds containing indolo[2,1-a]isoquinoline in moderate to excellent yield. The method enables the construction of three C-C bonds through an intramolecular carbopalladation, C-H activation, and a decarboxylation sequence. Furthermore, dihydrocyclohepta[de]naphthalene-fused indolo[2,1-a]isoquinolines can be synthesized in moderate yield by constructing a seven-membered ring.

Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation

A novel tandem intermolecular decarboxylative coupling reaction of o-bromobenzoic acids and aryl iodides has been developed. The method affords a range of unsymmetrically triphenylenes and displays unique regioselectivity and broad substrate scope. Mechanistically, palladium/norbornene-catalyzed C-H activation and subsequent double decarboxylative coupling reactions were involved. Moreover, the triphenylenes can also be synthesized from 2-iodobiphenyls and o-bromobenzoic acids under norbornene-free conditions.

Synthesis of dibenzo[: A, c] carbazoles from 2-(2-halophenyl)-indoles and iodobenzenes via palladium-catalyzed dual C-H functionalization

An efficient palladium-catalyzed strategy for the synthesis of dibenzo[a,c]carbazole derivatives has been developed. In the presence of Pd(OAc)2, 2-(2-halophenyl)-indoles and iodobenzenes proceeded smoothly to obtain the corresponding dibenzo[a

Copper-catalyzed synthesis of benzo[b]thiophene-fused imidazopyridines via the cleavage of C-H bond and C-X bond

A new and straightforward approach to synthesize benzo[b]thiophene-fused imidazopyridines has been developed by tandem cross-coupling reaction of K2S with 2-(2-bromophenyl)imidazo[1,2-a]pyridines, and K2S as sulfur source constructed

Synthesis and receptor binding studies of halogenated N,N-dialkylel-(2-phenyl-1H-indol-3-yl)glyoxylamides to visualize peripheral benzodiazepine receptors with SPECT or PET

A library of halogenated 2-arylindolyl-3-oxocarboxamides was prepared to develop radioligands to visualize cerebral PBR by SPECT and PET imaging. In vitro evaluation showed that most of the synthesized compounds were selective,high-affinity PBR ligands with adequate lipophilicity (log D7.4 in the range of 1.6-2.4). The iodinated derivative 11 (Ki = 2.6 nM) and the fluorinated analog 26 (Ki = 6.2 nM) displayed higher affinity than reference compounds.

Synthesis of phenanthrenes and polycyclic heteroarenes by transition-metal catalyzed cycloisomerization reactions

Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl2, AuCl, AuCl3, GaCl3 or InCl3 in toluene. This 6-endo-dig cyclization likely proceeds through initial π-complexation of the alkyne unit followed by interception of the resulting η2-metal species by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product. Moreover, it is readily extended to the heterocyclic series as exemplified by the preparation of benzoindoles, benzocarbazoles, naphthothiophenes, as well as bridgehead nitrogen heterocycles such as pyrrolo[1,2-a]quinolines. Depending on the chosen catalyst, biaryls bearing halo-alkyne units can either be converted into the corresponding 10-halo-phenanthrenes or into the isomeric 9-halo-phenanthrenes; in the latter case, the concomitant 1,2-halide shift is best explained by assuming a metal vinylidene species as the reactive intermediate. The scope of this novel method for the preparation of polycyclic arenes is illustrated by the total synthesis of a series of polyoxygenated phenanthrenes that are close relatives of the anticancer agent combretastatin A-4, as well as by the total synthesis of the aporphine alkaloid O-methyl-dehydroisopiline and its naturally occurring symmetrical dimer.