718616-47-8

Upstream product

• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 6164-80-3 pyridazine hydrochloride 
• 696-62-8 para-iodoanisole 
• 2164-61-6 pyridazine-3-carboxylic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1120-95-2 3-chloropyridazine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 65202-53-1 3-Iodopyridazine 

Relevant academic research and scientific papers

Direct C-H photoarylation of diazines using aryldiazonium salts and visible-light

In this study, direct C-H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% only by mixing and irradiating the reaction with no need for an additional photocatalyst. We demonstrate the efficacy of this protocol by the scope with electron-donor, -neutral, and -withdrawing groups attached at the ortho, meta, and para positions of the aryldiazonium salts; the results are better than those reported for ruthenium-complex mediated photoarylations. Additionally, we demonstrate the robustness of this methodology with a 5 mmol scaled-up experiment. Mechanistic studies were carried out giving support to the proposal of a photocatalyzed approach by an electron donor-acceptor (EDA) complex, also highlighting the crucial role that solvents play in the formation of the EDA complex. This journal is

Lewis Acid Directed Regioselective Metalations of Pyridazine

Mono- or bidentate boron Lewis acids trigger a regioselective magnesiation or zincation of pyridazine in position C3 (ortho product) or C4 (meta product). The regioselectivity of the metalation was rationalized with the help of calculated pKa values of both pyridazine and pyridazine/Lewis acid complexes.

Synthesis of functionalized 3-arylpyridazines via Pd-catalyzed decarboxylative cross-coupling of pyridazine-3-carboxylic acids

An efficient and general protocol for the decarboxylative cross-coupling of pyridazine-3-carboxylic acids with aryl-bromides has been described. This method provides a new avenue for the synthesis of 3-arylpyridazines via decarboxylative cross-coupling strategy by employing the dual-catalyst system of Pd(PPh3)4/Cu2O in the presence of Li2CO3at 160?°C in DMA.

Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles

Pyridazine N-oxides are used for the first time as precursors of metallocarbenes. These nitrogen-rich heterocycles led to the discovery of a novel acceptor and donor-acceptor enalcarbenoids. The synthetic utility of these metallocarbenes was demonstrated in the rhodium-catalyzed denitrogenative transannulation of pyridazine N-oxides with pyrroles to the valuable alkyl, 7-aryl, and 7-styryl indoles. The transannulation strategy was applied to the synthesis of a potent anticancer agent.

Use of N-oxide compounds in coupling reactions

Metal-catalyzed coupling process comprising reacting a compound of general formula 1 with a compound A-X, to obtain a compound of general formula 2, which may further be converted to a compound of general formula 3

Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides

New aspects of N-oxides: Pyrazine, pyridazine, and pyrimidine N-oxides are regioselectively arylated with aryl iodides, bromides, and chlorides in the presence of a palladium catalyst (see scheme). The resulting products can be deoxygenated in high yield

New pyrrolopyridazine derivatives as blue organic luminophors

New pyrrolopyridazine derivatives were synthesized as potential blue organic luminophors. Three different classes of pyrrolopyridazine derivatives were made, for example, aryl groups directly connected to the core PPY (pyrrolo[1,2-b]pyridazine-5,6,7-tricarboxylic acid trimethyl ester) moiety, aryl groups connected to the PPY via a vinylene linker and aryl groups connected to the PPY via an acetylene linker. Their optical and electrochemical properties were productively compared. One of the derivatives 2 showed a relative quantum yield as high as 0.9. Compound 8 in the vinyl bridged pyrrolopyridazine series has been characterized by its X-ray crystal structure analysis.