Spectral methods in the study of the structure of chromencarbonitriles, spiroindolinpyrrolizidinecarbonitriles and their transformation products
Andrey S. Kochukov1, Anna A. Meshcheryakova1, Alexander V. Nikulin1, Anna E. Sklyar1, Ekaterina A. Konstantinova2, K.-J. Ayena1, Nikolay I. Davydov1, Nikita A. Plotnikov1, Dmitry P. Vozyagin1, Nikita V. Oprishchenko1, Svetlana V. Borisova3, Adel P. Krivenko1, Vitaly V. Sorokin1; 1Saratov State University, Saratov, Russia; 2Institute of Biochemistry and Physiology of Plants and Microorganisms Russian Academy of Sciences, Saratov, Russia; 3Saratov State Medical University named after V.I. Razumovsky, Saratov, Russia
Abstract
This paper describes the determination of the structural features of new chromenes and spiroindolinpyrrolizidines with carbonitrile and other substituents using IR and NMR spectroscopy (1H, 13C). All compounds are formed based on ylidencarbonitriles obtained separately or formed as intermediates in multicomponent processes. Reactions of 1,3-dipolar cycloaddition leading to polysubstituted spiroindolinpyrrolizidines exhibit a certain regioselectivity, depending on the nature of the initial dipolarophile. To study the reactivity of chromencarbonitriles, they were subjected to halogenation or heterocyclization under the action of hydrazine. It has been established that the halogenation reactions of 2-aminotetrahydro-4H-chromen-3-carbonitriles proceed with the participation of the chromene fragment, without affecting other possible active sites. Chromencarbonitriles with N,N-binucleophilic reagents (hydrazine, hydrazides, phenylenediamine) give new chromenopyrazoles and chromenodiazepines. Conclusions about the course of transformations are made on the basis of spectral studies of reaction products and intermediates.
Speaker
Andrey S. Kochukov
Saratov State University
Russia
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