103344-69-0Relevant academic research and scientific papers
Divergent synthesis of (quinoxalin-2-yl)-1,3-oxazines and pyrimido[1,6-a]quinoxalines via the cycloaddition reaction of acyl(quinoxalinyl)ketenes
Kasatkina, Svetlana,Stepanova, Ekaterina,Dmitriev, Maksim,Mokrushin, Ivan,Maslivets, Andrey
supporting information, (2019/09/06)
A facile synthetic approach towards two distinct quinoxaline-based heterocyclic scaffolds has been developed from the cycloaddition of acyl(quinoxalinyl)ketenes with carbodiimides. The described reaction represents the first example of a divergent synthesis based on acyl(quinoxalinyl)ketenes providing (quinoxalin-2-yl)-1,3-oxazines or pyrimido[1,6-a]quinoxalines depending on the type of the acyl substituent in the ketenes. The key reactants, acyl(quinoxalinyl)ketenes, are generated in situ via the thermal decarbonylation of readily available pyrroloquinoxaline oxo-derivatives. The proposed diversity-oriented synthesis provides facile access to a library of skeletally diverse pharmaceutically interesting quinoxaline-based heterocycles from inexpensive reagents.
One-Pot Synthesis of Thieno[3,2- e]pyrrolo[1,2- a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors
Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.
supporting information, p. 15788 - 15796 (2019/12/25)
A new, efficient, and versatile one-pot cascade reaction of diverse Gewald's aminothiophenes, 2-hydroxy-4-oxobut-2-enoic acid, and derivatives of cyanoacetic acid catalyzed by Et3N is presented. It enables direct synthesis of diverse 1-(2-oxoethylidene)-2-oxothieno[3,2-e]pyrrolo[1,2-a]pyrimidine in good to excellent yields. The reaction exhibits a broad substrate scope and also presents an opportunity for further modification of the structure. The method offers a convenient practical alternative to the known procedures. The synthesized thieno[3,2-e]pyrrolo[1,2-a]pyrimidine scaffold is an important structural motif of new poly(ADP-ribose) polymerase (PARP) inhibitors, playing a useful role in multiple pharmacological applications.
(Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives
Banville, Jacques,Bouthillier, Gilles,Plamondon, Serge,Remillard, Roger,Meanwell, Nicholas A.,Martel, Alain,Walker, Michael A.
scheme or table, p. 3170 - 3173 (2010/08/05)
The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected α,γ-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric a
Reactions of acylpyruvic acids and 2,3-dihydrofuran-2,3-diones with 2,3-diaminopyridine
Sof'ina,Igidov,Koz'minykh,Trapeznikova,Kasatkina,Koz'minykh
, p. 1017 - 1025 (2007/10/03)
Acylpyruvic acids readily react with 2,3-diaminopyridine to form (Z)-3-acylmethylene-1H-3,4-dihydropyrido[2,3-b]pyrazin-2-ones. 5-Aryl-2,3-dihydrofuran-2,3-diones which can be regarded as lactones derived from γ-enolized aroylpyruvic acids react with 2,3-diaminopyridine under mild conditions, yielding regioisomeric (Z)-2-aroylmethylene-4H-1,2-dihydropyrido[2,3-b]pyrazin-3-ones. The structure of the products and reaction chemoselectivity are discussed.
CHEMISTRY OF OXALYL DERIVATIVES OF METHYL KETONES. XLII. RING OPENING IN 5-ARYL-2,3-DIHYDRO-2,3-FURANDIONES BY THE ACTION OF AROMATIC AMINES IN TOLUENE. EFFECT OF SUBSTITUENTS IN THE NUCLEOPHILIC REAGENTS AND SUBSTRATE ON THE RATE OF THE NONCATALYTIC REAC
Kozlov, A. P.,Sychev, D. I.,Andreichikov, Yu. S.
, p. 1965 - 1972 (2007/10/02)
The kinetics of the reactions of 5-aryl-2,3-dihydro-2,3-furandiones with aromatic amines were investigated by a spectrophotometric method.On the basis of an analysis of the dependence of the reaction rate on the nature of the substituents in the substrate
