Synthesis and properties of bis(pyrazino[2′,3′:4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes: a new fluorescent nitrogen-rich heterocycle

被引：10

作者：

Hachiya, Sojiro ^{[1
]}

Hashizume, Daisuke ^{[2
]}

Maki, Shojiro ^{[1
]}

Niwa, Haruki ^{[1
]}

Hirano, Takashi ^{[1
]}

机构：

[1] Univ Electrocommun, Dept Appl Phys & Chem, Tokyo 1828585, Japan

[2] RIKEN, Adv Technol Support Div, Wako, Saitama 3510198, Japan

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 10期

基金：

日本科学技术振兴机构;

关键词：

PALLADIUM-CATALYZED AMINATION; AUTO-TANDEM CATALYSIS; LIGHT-EMITTING MOIETY; ARYL HALIDES; CYPRIDINA BIOLUMINESCENCE; AZA ANALOGS; BODIPY DYES; C-N; LUCIFERIN; BENZO;

D O I：

10.1016/j.tetlet.2010.01.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrogen-rich heterocycles, bis(pyrazino[2',3':4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes (BPI-HAAs) were prepared by conventional Pd(OAc)(2)/BINAP-catalyzed C-N coupling reactions of 5-aryl-3-bromoaminopyrazines. The BPI-HAA core is a planar structure with aromaticity, and this heterocycle exhibits red fluorescence and moderate electron-accepting characteristics. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1401 / 1403

页数：3

共 50 条

[21] SYNTHESIS OF [1,2,3]TRIAZOLO[4′,5′:4,5]PYRIMIDO[1,6-a]BENZIMIDAZOLE, A NEW HETEROCYCLIC SYSTEM
Pokhodylo, N. T.
Matiychuk, V. S.
Obushak, M. D.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (02) : 245 - 247
[22] Synthesis of new pyridazino [4',3':4,5]-thieno[3,2-d]-1,2,3-triazine and pyrimido[4',5':4,5]thieno[2,3-c]pyridazine derivatives
Quintela, JM
Veiga, MC
AlvarezSarandes, R
Gonzalez, L
Peinador, C
MONATSHEFTE FUR CHEMIE, 1996, 127 (10): : 1037 - 1043
[23] Synthesis of new pyrido[4",3":4′,5′]thieno[2′,3′:4,5]pyrimido-[2,1-B][1,3,4]thiadiazine derivatives
Ahmed, EK
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (04) : 989 - 1000
[24] 1,3-THIAZOLIDINIC AND 2,4,5,6-TETRAHYDRO-1,3-THIAZINIC SPIROCHROMENES AND MEROCYANINES - SYNTHESIS, REACTIVITY AND PHOTOCHROMIC PROPERTIES
MAGUET, M
POIRIER, Y
GARNIER, F
GUGLIELMETTI, R
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1979, 6 (1-2): : 193 - 194
[25] SYNTHESIS OF 11-ARYL-7,8,9,10-TETRAHYDRO-1,2,3-TRIAZINO-[4',5'-4,5]THIENO[2,3-B]CHINOLINES WITH ANTIANAPHYLACTIC ACTIVITY
WAGNER, G
VIEWEG, H
LEISTNER, S
PHARMAZIE, 1993, 48 (08): : 576 - 578
[26] SYNTHESIS OF NEW FUSED HETEROCYCLES BY ANNELATION OF THIOPYRANO[4',3'/4,5]THIENO[2,3-C]PYRIMIDINES
AHMED, EK
MONATSHEFTE FUR CHEMIE, 1995, 126 (8-9): : 953 - 959
[27] Synthesis and neurotropic activity of new pyrano[4′,3′:4,5]thieno[2,3:4″,5″]pyrimido[2,3-c]-(1,2,4 )triazines
Oganisyan A.Sh.
Grigoryan G.O.
Noravyan A.S.
Dzhagatspanyan I.A.
Melikyan G.G.
Pharmaceutical Chemistry Journal, 2001, 35 (3) : 124 - 126
[28] Cycloalkano[1",2":4,5;4",3":4′,5′]bis(pyrrolo[2,3-c]pyrimido-[5,4-e]pyridazines):: synthesis, structure and mechanism of their formation
Serduke, OV
Gulevskaya, AV
Pozharskii, AF
Starikova, ZA
Profatilova, IA
TETRAHEDRON, 2006, 62 (04) : 652 - 661
[29] HETEROCYCLIC FUSED RINGS WITH BRIDGEHEAD NITROGEN-ATOMS - SINGLE-STEP SYNTHESIS OF AZOLO[5'',1''-3',4'][1,2,4]TRIAZINO-[5',6'-4,5]PYRIMIDO[1,6-A]BENZIMIDAZOLES
FARAG, AM
JOURNAL OF CHEMICAL RESEARCH-S, 1994, (11): : 432 - 433
[30] Synthesis and 5-hydroxytryptamine (5-HT) activity of 2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5-(6H)ones and 2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoxalines
Welmaker, GS
Nelson, JA
Sabalski, JE
Sabb, AL
Potoski, JR
Graziano, D
Kagan, M
Coupet, J
Dunlop, J
Mazandarani, H
Rosenzweig-Lipson, S
Sukoff, S
Zhang, YX
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) : 1991 - 1994

← 1 2 3 4 5 →