55825-40-6Relevant academic research and scientific papers
One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives
Ananikov, Valentine P.,Ledovskaya, Maria S.,Polynski, Mikhail V.
, p. 2286 - 2297 (2021/07/20)
Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2?H2O mixture performed in a two-chamber reactor led to the corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95–99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.
Selective mono-amination of dichlorodiazines
Sengmany, Stéphane,Lebre, Julie,Le Gall, Ewan,Léonel, Eric
, p. 4859 - 4867 (2015/08/03)
A mild, easy-to-perform, and versatile method for the formation of aminochlorodiazines from reaction of several types of dichlorodiazines (i.e., pyridazines, pyrimidines, and pyrazines) with primary or secondary amines in ethanol in the presence of trieth
An electrochemical nickel-catalyzed arylation of 3-amino-6- chloropyridazines
Sengmany, Stephane,Vitu-Thiebaud, Arnaud,Le Gall, Erwan,Condon, Sylvie,Leonel, Eric,Thobie-Gautier, Christine,Pipelier, Muriel,Lebreton, Jacques,Dubreuil, Didier
, p. 370 - 379 (2013/03/13)
3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.
Delta 1-pyrrolines used as pesticides
-
, (2008/06/13)
Novel Δ1-pyrrolines of the formula (I) in which R1, R2, R3, m and Q have the meanings given in the description, a plurality of processes for preparing these substances and their use for controlling pests.
Quinoxaline studies. 23. Potential antimalarials. Substituted 5,8-dimethoxy-6-[N-(omega-dimethylaminoalkyl)amino]quinoxalines were prepared: the first series with identical 2,3-substituents H, CH3, C6H5, C6H4-4-Cl, and CH2C6H5; and the second with identical styryl groups CH=CHC6H5, CH=CHC6H4-4-Cl, CH=CHC6H3-3,4-Cl2, CH=CHC6H4-4-F, CH=CHC6H4-4-CF3, and CH=CHC6H4-4-NO2. None of the substances
Pifferi,Parravicini,Carpi,Dorigotti
, p. 741 - 746 (2007/10/04)
3-Hydrazinopyridazines substituted in position 6 with a primary amine, secondary amine, or an alkoxy group were synthesized and screened for antihypertensive activity. In general, the 6-dialklamino derivatives are the most active; the (2-hydroxypropyl)methylamino chain provides the best combination of high antihypertensive activity and toxicity.
