Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline

被引：1

作者：

Azev, Yu. A. ^{[1
]}

Koptyaeva, O. S. ^{[1
]}

Eltsov, O. S. ^{[1
]}

Yakovleva, Yu. A. ^{[1
]}

Tsmokalyuk, A. N. ^{[1
]}

Ivoilova, A. V. ^{[1
]}

Seliverstova, E. A. ^{[1
]}

Pospelova, T. A. ^{[1
]}

Bakulev, V. A. ^{[1
]}

机构：

[1] Ural Fed Univ, Ekaterinburg 620002, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2020年 / 90卷 / 09期

关键词：

arylhydrazones; indole-3-carbaldehydes; C; C-coupling; quinazoline; trifluoro hydrazides; DENSITY-FUNCTIONAL THEORY;

D O I：

10.1134/S1070363220090030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7 ' of the hydrazone molecule and has afforded the sigma-adducts. The C,C-coupling has been accompanied by a change in theE-configuration of the C=N bond of the starting hydrazones to theZ-configuration in the formed quinazoline trifluoroacetyl hydrazides.

引用

页码：1601 / 1610

页数：10

共 23 条

[1] Anastas P.T., 1998, GREEN CHEM THEORY PR, P516
[2] Aniszewski T, 2015, ALKALOIDS, V2nd ed.
[3] Chemical Characteristics, Synthetic Methods, and Biological Potential of Quinazoline and Quinazolinone Derivatives
Asif, Mohammad
[J]. INTERNATIONAL JOURNAL OF MEDICINAL CHEMISTRY, 2014, 2014
[4] Synthesis of Stable σ-Adducts by Arylation of Quinazoline
Azev, Yu. A.
Koptyaeva, O. S.
Seliverstova, E. A.
Ivoilova, A. V.
Pospelova, T. A.
[J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (12) : 2374 - 2377
[5] Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles
Azev, Yuri A.
Shorshnev, Sergey V.
Golomolzin, Boris V.
[J]. TETRAHEDRON LETTERS, 2009, 50 (24) : 2899 - 2903
[6] Finding the Reactive Electron in Paramagnetic Systems: A Critical Evaluation of Accuracies for EPR Spectroscopy and Density Functional Theory Using 1,3,5-Triphenyl Verdazyl Radical as a Testcase
Barilone, Jessica
Neese, Frank
van Gastel, Maurice
[J]. APPLIED MAGNETIC RESONANCE, 2015, 46 (02) : 117 - 139
[7] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[8] Chadha N., 2018, KEY HETEROCYCLE CORE, P285, DOI DOI 10.1016/B978-0-08-102083-8.00008-X
[9] Charushin V.N., 2014, Metal Free CH Functionalization of Aromatics, P1, DOI DOI 10.1007/7081_2013_119
[10] Quinazoline alkaloids in nature
D'yakonov A.L.
Telezhenetskaya M.V.
[J]. Chemistry of Natural Compounds, 1997, 33 (3) : 221 - 267

← 1 2 3 →