1244024-26-7Relevant articles and documents
Transition-Metal-Free Synthesis of Pyrrolo[1,2- a ]pyrazines via Intramolecular Cyclization of N -Propargyl(pyrrolyl)enaminones
Sobenina, Lyubov N.,Sagitova, Elena F.,Ushakov, Igor A.,Trofimov, Boris A.
, p. 4065 - 4081 (2017)
A concise transition-metal-free strategy for the synthesis of pyrrolo[1,2- a ]pyrazines with enone substituents has been developed. It includes the following key steps: (a) cross-coupling of pyrroles with acyl(bromo)acetylenes in solid alumina at room temperature to give 2-(acylethynyl)pyrroles; (b) addition of propargylamine to the above acetylenes to form the corresponding N -propargylenaminones; and (c) chemo- and stereoselective base-catalyzed (Cs 2 CO 3 /DMSO) intramolecular cyclization of the synthesized propargylic derivatives to form (acylmethylidene)pyrrolo[1,2- a ]pyrazines of Z -configuration.
Functionalized Bipyrroles and Pyrrolyl-Aminopyrones from Acylethynylpyrroles and Diethyl Aminomalonate
Gotsko, Maxim D.,Kireeva, Victoriya V.,Saliy, Ivan V.,Sobenina, Lyubov N.,Trofimov, Boris A.,Ushakov, Igor A.
, (2021/12/29)
An efficient method for the synthesis of 1H,1?H-2,3?-bipyrroles (up to 72% yield) by the cyclocondensation of easily available 2-(acylethynyl)pyrroles with diethyl aminomalonate hydrochloride has been developed. The reaction proceeds under reflux in MeCN
Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine
Vasilevsky, Sergei F.,Davydova, Maria P.,Tomilin, Denis N.,Sobenina, Lyubov N.,Mamatuyk, Victor I.,Pleshkova, Nadezhda V.
, p. 132 - 144 (2014/08/18)
The reaction of diarylketoacetylenes with ethylenediamine (EDA) leads to arylmethylketones and 2-substituted imidazoline derivatives. This transformation involves complete cleavage of the triple bond via initial intermolecular Michael-addition with subsequent intramolecular Michaeladdition. Final fragmentation can be presented as a retro-Mannich reaction, accompanied by three formal reductive stages (formation of three C-H bonds), while the other carbon undergoes a formal oxidation, in which three C-N bonds (C-N and C=N) are formed. ARKAT-USA, Inc.