6(7)-Acylperimidines nitration and methods of peri-annelation on this base

被引：2

作者：

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

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

Lyakhovnenko, A. S. ^{[1
]}

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

Levina, I. I. ^{[2
]}

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

机构：

[1] North Caucasus Fed Univ, Stavropol 355009, Russia

[2] NM Emanuel Inst Biochem Phys, Moscow 119991, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 49卷 / 07期

基金：

俄罗斯基础研究基金会;

关键词：

formic acid; perimidines; polyphosphoric acid; sodium azide; sodium nitrite; 1,3,6,8-tetraazapyrenes; 1H-1,5,7-triazacyclopenta[cd]phenalenes; zinc; nitration; Schmidt reaction; ELECTRON-TRANSFER; DERIVATIVES; SEMICONDUCTORS;

D O I：

10.1007/s10593-013-1335-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method has been developed for the nitration of 6(7)-acylperimidines using sodium nitrite in formic acid. The reaction gives a mixture of 4(9)-, 9(4)-, and 7(6)-nitro-6(7)-acylperimidines from which the latter can be separated by extraction with chloroform. Reduction of the 6(7)-acyl-7(6)-nitro- perimidines yields 1H-1,5,7-triazacyclopenta[cd]phenalenes. Subsequent Schmidt reaction and reduction give 1,3,6,8-tetraazapyrenes.

引用

收藏

页码：980 / 987

页数：8

相关论文

共 29 条

[11] A new method for pyrrole peri-annulation: synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes from 1H-perimidines [J].

Aksenov, Alexander V. ;

Lyakhovnenko, Alexander S. ;

Andrienko, Anna V. ;

Levina, Irina I. .

TETRAHEDRON LETTERS, 2010, 51 (18) :2406-2408

[12] Photoinduced energy-electron transfer studies with naphthalene diimides [J].

Alp, S ;

Erten, S ;

Karapire, C ;

Köz, B ;

Doroshenko, AO ;

Içli, S .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2000, 135 (2-3) :103-110

[13] Analgesic activity of cyclic imides:: 1,8-naphthalimide and 1,4,5,8-naphthalenediimide derivatives [J].

Andricopulo, AD ;

Müller, LA ;

Cechinel, V ;

Cani, GS ;

Roos, JF ;

Corrêa, R ;

Santos, ARS ;

Nunes, RJ ;

Yunes, RA .

FARMACO, 2000, 55 (04) :319-321

[14] Constructing molecular machinery: A chemically-switchable [2]catenane [J].

Balzani, V ;

Credi, A ;

Langford, SJ ;

Raymo, FM ;

Stoddart, JF ;

Venturi, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3542-3543

[15] DNA binding properties of 2,7-diazapyrene and its N-methylated cations studied by linear and circular dichroism spectroscopy and calorimetry [J].

Becker, HC ;

Norden, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (25) :5798-5803

[16] PHOTOCHEMISTRY OF INTERCALATED QUATERNARY DIAZAAROMATIC SALTS [J].

BRUN, AM ;

HARRIMAN, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8153-8159

[17] DYNAMICS OF ELECTRON-TRANSFER BETWEEN INTERCALATED POLYCYCLIC MOLECULES - EFFECT OF INTERSPERSED BASES [J].

BRUN, AM ;

HARRIMAN, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (10) :3656-3660

[18] SOME DERIVATIVES OF 1-6-DIAZAPYRENE AND 4-5-6-7-DIBENZO-1-3-DIAZACYCLOHEPTA-2-4-6-TRIENE [J].

FAIRFULL, AES ;

PEAK, DA ;

SHORT, WF ;

WATKINS, TI .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC) :4700-4709

[19] 1,3,6,8-Tetraazapyrenes: Synthesis, Solid-State Structures, and Properties as Redox-Active Materials [J].

Geib, Sonja ;

Martens, Susanne C. ;

Zschieschang, Ute ;

Lombeck, Florian ;

Wadepohl, Hubert ;

Klauk, Hagen ;

Gade, Lutz H. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14) :6107-6116

[20] Preparation, characterization and DNA photocleavage of diazapyrene-tethered oligothymidylates [J].

Ikeda, H ;

Fuji, K ;

Tanaka, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (01) :101-104