Sukhanova Anna Alekseevna
@zioc.ru
N.D. Zelinsky Institute of Organic Chemistry
RESEARCH, TEACHING, or OTHER INTERESTS
Organic Chemistry
Scopus Publications
Scopus Publications
A. A. Sukhanova, M. A. Present, S. V. Baranin, and A. N. Fakhrutdinov
Springer Science and Business Media LLC
A. A. Sukhanova, M. A. Prezent, A. N. Fakhrutdinov, and I. V. Zavarzin
Springer Science and Business Media LLC
Alexander V. Komkov, Anna А. Sukhanova, Leonid G. Menchikov, and Igor V. Zavarzin
Springer Science and Business Media LLC
Anna A. Sukhanova, Maxim I. Zuev, Mikhail A. Prezent, Alexey N. Proshin, Sergey V. Baranin, and Yurii N. Bubnov
Elsevier BV
Maxim A. Zuev, Anna A. Sukhanova, Alena G. Smola, Mikhail A. Prezent, Alexey N. Proshin, Sergey V. Baranin, and Yurii N. Bubnov
Elsevier BV
Anna A. Sukhanova, Ilya A. Puchkin, Andrei A. Vasil'ev, and Sergei G. Zlotin
Elsevier BV
Anna A. Sukhanova, Yulia V. Nelyubina, and Sergei G. Zlotin
Elsevier BV
Alexey Yu. Sukhorukov, Anna A. Sukhanova, and Sergei G. Zlotin
Elsevier BV
Mikhail S. Novikov, Alexander F. Khlebnikov, Nikolai V. Rostovskii, Sergei Tcyrulnikov, Anna A. Suhanova, Kirill V. Zavyalov, and Dmitry S. Yufit
American Chemical Society (ACS)
Transformations of 2-azabuta-1,3-dienes, formed in Rh2(OAc)4-catalyzed reactions of diazo carbonyl compounds with 2H-azirines, dramatically depend on the nature of substituents. 4,4-Diphenyl-2-azabuta-1,3-dienes with two electron-acceptor substituents at C(1) undergo thermal 1,5-cyclization to give indoles in good yields. The increase in electron-withdrawing ability of C(1)-substituents facilitates the reaction that proceeds via pseudopericyclic 1,5-electrocyclization of 2-azabutadiene into 7aH-indolium ylide followed by prototropic shift. 3,4-Diphenyl-2-azabuta-1,3-dienes, resulting from reaction of 2,3-diphenyl-2H-azirine and diazo compounds, do not produce indoles via 1,5-cyclization due to the trans-configuration of the 4-Ph-group and the nitrogen, but undergo 1,4-cyclization to 2,3-dihydroazetes. 1,6-Cyclization into 2H-1,4-oxazines with participation of the oxygen of ester or amide group at C(1) of corresponding 2-azabuta-1,3-dienes does not take place due to kinetic and thermodynamic reasons. Instead of this, 1,6-electrocyclization with participation of phenyl substituent at C(4) of the 2-azabuta-1,3-dienes, providing isoquinoline derivatives, can occur at elevated temperatures. The DFT-calculations (mPWB1K/6-31+G(d,p)) confirm the dependence of 2-azabuta-1,3-diene transformation type on the nature of substituents.
Sergei G. Zlotin, Galina V. Kryshtal, Galina M. Zhdankina, Anna A. Sukhanova, Alexander S. Kucherenko, Boris B. Smirnov, and Vladimir A. Tartakovsky
Elsevier BV