SYNTHESIS OF POLYAZAMACROCYCLES COMPRISING 6,6′-DIAMINO-2,2′-BIPYRIDINE MOIETIES VIA Pd-CATALYZED AMINATION

被引：8

作者：

Averin, Alexei D. ^{[1
]}

Uglov, Alexei N. ^{[1
]}

Buryak, Alexei K. ^{[2
]}

Bessmertnykh, Alla G. ^{[3
]}

Guilard, Roger ^{[3
]}

Beetskaya, Irina P. ^{[1
,2
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[2] AN Frumkin Inst Phys & Electrochem, Moscow 119991, Russia

[3] ICMUB, UMR 5260, CNRS, F-21078 Dijon, France

来源：

HETEROCYCLES | 2010年 / 80卷 / 02期

关键词：

2,2 '-Bipyridine; Amination; Polyamine; Pd Catalysis; Macrocycle; UP-HILL TRANSPORT; MOLECULAR RECOGNITION; MACROCYCLIC LIGAND; BIPYRIDINE; COMPLEXES; UNITS; ARYL; 2,2-BIPYRIDINE; PHENANTHROLINE; COORDINATION;

D O I：

10.3987/COM-09-S(S)68

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed amination of 6,6'-dibromo-2,2'-bipyridine with a variety of di-, tri-, tetraamines and oxadiamines was carried out for the synthesis of a new class of polyazamacrocycles comprising a 6,6'-diamino-2,2'-bipyridine unit. The obtained results of the catalytic amination reaction were shown to be dramatically dependent on the nature of the amines, mainly on the length of the amine chain. The shortest propane-1,3-diamine and butane-1,4-diamine derivatives provided only cyclic dimers whereas the longest di- and trioxadiamines gave desired macrocycles in very good yields. The formation of cyclic oligomers was observed in all cases. Different reaction conditions leading to cyclic dimers were explored.

引用

页码：957 / 975

页数：19

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