Synthesis, photophysical, and electrochemical properties of 2,5-diaryl-indolizines

被引:27
作者
Amaral, Monica F. Z. J. [1 ,2 ]
Deliberto, Laila A. [1 ,4 ]
de Souza, Camila R. [1 ,2 ]
Naal, Rose M. Z. G. [1 ,3 ]
Naal, Zeki [1 ,3 ]
Clososki, Giuliano C. [1 ,2 ]
机构
[1] Univ Sao Paulo, Fac Ciancias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP, Brazil
[2] Nucleo Pesquisas Prod Nat & Sintet, BR-14040903 Ribeirao Preto, SP, Brazil
[3] Inst Nacl Ciencias & Tecnol Bioanalit, BR-13083970 Campinas, SP, Brazil
[4] Univ Sao Paulo, Fac Filosofia Ciancias & Letras Ribeirao Preto, BR-14040903 Ribeirao Preto, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Indolizine; Photophysical properties; Electrochemical properties; Cross-coupling reaction; Organozinc compounds; ANION FORMATION; DERIVATIVES; INDOLIZINES; PYRIDINIUM; FRAMEWORK; BEARING; DESIGN; PROBES;
D O I
10.1016/j.tet.2013.11.105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of novel 2,5-dialyl-indolizines have been prepared through the palladium-catalyzed cross-coupling reactions of organozinc reagents prepared from 2-aryl-indolizines with aromatic halides. The photophysical properties of representative compounds indicate that the 2,5-diaryl-indolizines are promising candidates to be used in optoelectronic devices and biomolecular labeling. In addition, cyclic voltammetry studies of some nitrophenyl-substituted indolizines have shown evidences of an oxidation process without the correspondent reduction peak suggesting a dimerization reaction. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3249 / 3258
页数:10
相关论文
共 70 条
[1]  
Allen WE, 2001, CHEM-EUR J, V7, P721, DOI 10.1002/1521-3765(20010202)7:3<721::AID-CHEM721>3.0.CO
[2]  
2-1
[3]   RADICAL CATIONS .2. OXIDATIVE DIMERIZATION OF INDOLIZINES - A CHEMICAL AND ELECTROCHEMICAL INVESTIGATION [J].
ANDRUZZI, R ;
CARDELLINI, L ;
GRECI, L ;
STIPA, P ;
POLONI, M ;
TRAZZA, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3067-3070
[4]   HETEROCYCLIZATIONS IN THE PYRIDO[2,3-B]PYRAZINE SERIES [J].
BLACHE, Y ;
GUEIFFIER, A ;
CHAVIGNON, O ;
TEULADE, JC ;
MILHAVET, JC ;
VIOLS, H ;
CHAPAT, JP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (01) :161-166
[5]   INDOLIZINE STUDIES .2. SYNTHESIS AND NMR SPECTROSCOPIC ANALYSIS OF 2-SUBSTITUTED INDOLIZINES [J].
BODE, ML ;
KAYE, PT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (15) :1809-1813
[6]   FORMATION OF PYRROCOLINES BY REACTION OF DIMETHYL ACETYLENEDICARBOXYLATE WITH HETEROCYCLIC ZWITTERIONS [J].
BOEKELHEIDE, V ;
FAHRENHOLTZ, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (02) :458-&
[7]   Nitroradical anion formation from some iodo-substituted nitroimidazoles [J].
Bollo, S ;
Núñez-Vergara, LJ ;
Barrientos, C ;
Squella, JA .
ELECTROANALYSIS, 2005, 17 (18) :1665-1673
[8]   2-ARYLPYRROCOLINES AND 2-ARYLPYRIMIDAZOLES [J].
BUUHOI, NP ;
JACQUIGNON, P ;
XUONG, ND ;
LAVIT, D .
JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (08) :1370-1375
[9]   Fluorescent small-molecule probes of biochemistry at the plasma membrane [J].
Cairo, Christopher W. ;
Key, Jessie A. ;
Sadek, Christopher M. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (01) :57-63
[10]   A practical parallel synthesis of 2-substituted indolizines [J].
Chai, WY ;
Kwok, A ;
Wong, V ;
Carruthers, NI ;
Wu, JJ .
SYNLETT, 2003, (13) :2086-2088