Macrocycles, derivatives of nitrogen-containing heterocycles 2. Synthesis and electrochemical properties of diindolizinadiquinoxalinacyclooxaalkaphanes

被引：3

作者：

Kalinin, A. A. ^{[1
]}

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

Yanilkin, V. V. ^{[1
]}

Nastapova, N. V. ^{[1
]}

Rizvanov, I. Kh. ^{[1
]}

Morozov, V. I. ^{[1
]}

机构：

[1] Russian Acad Sci, Kazan Sci Ctr, AE Arbuzov Organ & Phys Chem Inst, Kazan 420088, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2009年 / 58卷 / 07期

基金：

俄罗斯基础研究基金会;

关键词：

1; n-dibromotrioxa- and pentaoxaalkanes; 3-(indolizin-2 '-yl)-2-oxoquinoxalinomonopodands; diquinoxalinadiindolizinacyclooxaalkaphanes; redox-active macrocycles; NMR spectra; voltammetry; ESR; electron ionization and MALDI mass spectra; REDOX; DIMERIZATION; INDOLIZINES;

D O I：

10.1007/s11172-009-0200-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phenylindolizinylquinoxalinomonopodands, obtained by the reaction of 1-(phenylindolizin-2-yl)quinoxalin-2(1H)-one with corresponding dibromotrioxa- and dibromopentaoxaalkanes, undergo oxidative dehydrocyclization assisted by molecular iodine to yield new redox-active diindolizinadiquinoxalinacyclooxaalkaphanes. Using CVA, the indolizine fragments of the heterocyclophanes in acetonitrile are found to undergo three-step oxidation with transfer of one electron in each step. The first and the third steps are reversible, whereas the second is irreversible. The oxidation at potentials of the first peak leads to the stable radical cations registered by ESR (g = 2.0024, a (2N) = 0.26 mT).

引用

页码：1484 / 1492

页数：9

共 19 条

[11] FACILE DEHYDROGENATIVE DIMERIZATION OF INDOLIZINE DERIVATIVES
KAKEHI, A
ITO, S
HAMAGUCHI, A
OKANO, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (09) : 2833 - 2834
[12] Molecular design and applications of photochromic crown compounds - How can we manipulate metal ions photochemically?
Kimura, K
Sakamoto, H
Nakamura, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (02) : 225 - 245
[13] Switchable electron-rich biindolizine-based macrocycles: synthesis and redox properties
Kreher, T
Sonnenschein, H
Costisella, B
Schneider, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (22): : 3451 - 3457
[14] Diastereoisomerism and electrochemical behaviour - An investigation of redox-active cyclophanes
Leitner, MB
Kreher, T
Sonnenschein, H
Costisella, B
Springer, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (02): : 377 - 381
[15] Synthesis, structure, and electrochemical properties of 12,42-dioxo-21,31-diphenyl-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2(2,3), 3(3,2)-diindolizinacyclopentadecaphane
Mamedov, V. A.
Kalinin, A. A.
Yanilkin, V. V.
Nastapova, N. V.
Morozov, V. I.
Balandina, A. A.
Gubaidullin, A. T.
Isaikina, O. G.
Chernova, A. V.
Latypov, Sh. K.
Litvinov, I. A.
[J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (10) : 2060 - 2073
[16] 3-Indolizin-2-ylquinoxalines and the derived monopodands
Mamedov, VA
Kalinin, AA
Yanilkin, VV
Gubaidullin, AT
Latypov, SK
Balandina, AA
Isaikina, OG
Toropchina, V
Nastapova, NV
Glamova, NA
Litvinov, LA
[J]. RUSSIAN CHEMICAL BULLETIN, 2005, 54 (11) : 2616 - 2625
[17] Sonnenschein H, 1998, SYNTHESIS-STUTTGART, P1596
[18] Novel redox-active cyclophanes based on 3,3'-biindolizines: Synthesis and chirality
Sonnenschein, H
Kreher, T
Grundemann, E
Kruger, RP
Kunath, A
Zabel, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 710 - 714
[19] YANILKIN VV, 2007, ELEKTROKHIMIYA, V43, P808

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