A new approach to the 1,10-phenanthroline core

被引:23
作者
Chelucci, Giorgio [1 ]
Addis, Daniele [1 ]
Baldino, Salvatore [1 ]
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
1,10-phenanthroline; nitrogen heterocycles; intramolecular coupling; Ullmann reaction;
D O I
10.1016/j.tetlet.2007.03.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of eiv-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinalclehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3359 / 3362
页数:4
相关论文
共 34 条
[1]  
[Anonymous], 1978, ADV HETEROCYCL CHEM
[2]   Photoactive mono- and polynuclear Cu(I)-phenanthrolines. A viable alternative to Ru(II)-polypyridines? [J].
Armaroli, N .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (02) :113-124
[3]   Synthesis of mono- and dialkylsubstituted 1,10-phenanthrolines [J].
Belser, P ;
Bernhard, S ;
Guerig, U .
TETRAHEDRON, 1996, 52 (08) :2937-2944
[4]   Synthesis of efficient blue and red light emitting phenanthroline derivatives containing both hole and electron transporting properties [J].
Bing, YJ ;
Leung, LM ;
Menglian, G .
TETRAHEDRON LETTERS, 2004, 45 (33) :6361-6363
[5]   Synthesis of a linear bis-porphyrin with a Ru(phen)22+-complexed 2,2′-bipyridine spacer [J].
Bruce, JI ;
Chambron, JC ;
Kölle, P ;
Sauvage, JP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (10) :1226-1231
[6]   SYNTHESIS OF SOME 2,9-DISUBSTITUTED-1,10-PHENANTHROLINES [J].
CHANDLER, CJ ;
DEADY, LW ;
REISS, JA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (03) :599-601
[7]   Chiral 2,2′-bipyridines, 1,10-phenanthrolines, and 2,2′:6′,2"-terpyridines:: Syntheses and applications in asymmetric homogeneous catalysis [J].
Chelucci, G ;
Thummel, RP .
CHEMICAL REVIEWS, 2002, 102 (09) :3129-3170
[8]   Chiral phenanthrolines as ligands for Cu(I)-catalyzed asymmetric allylic oxidation [J].
Chelucci, G ;
Iuliano, A ;
Muroni, D ;
Saba, A .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 191 (01) :29-33
[9]   Synthesis of chiral C2-symmetric 1,10-phenanthrolines from naturally occurring monoterpenes [J].
Chelucci, G ;
Loriga, G ;
Murineddu, G ;
Pinna, GA .
SYNTHESIS-STUTTGART, 2003, (01) :73-78
[10]   Synthesis and application in asymmetric copper(I)-catalyzed allylic oxidation of a new chiral 1,10-phenanthroline derived from pinene [J].
Chelucci, G ;
Loriga, G ;
Murineddu, G ;
Pinna, GA .
TETRAHEDRON LETTERS, 2002, 43 (19) :3601-3604