Displacement reactions of 2-chloro- and 2,9-dichloro-1,10-phenanthroline: synthesis of a sulfur-bridged bis-1,10-phenanthroline macrocycle and a 2,2 '-amino-substituted-bis-1,10-phenanthroline

作者：Krapcho A Paul^*; Sparapani Silvia; Leenstra Amber; Seitz Joshua D

来源：Tetrahedron Letters, 2009, 50(26): 3195-3197.

DOI：10.1016/j.tetlet.2009.01.138

• 9-Chloro-1,10-phenanthroline-2(1H)-thione
• 1,10-Dihydro-1,10-phenanthroline-2,9-dithione
• Sulfur-bridged bis-1,1-phenanthroline macrocycle
• 2-Amino- and 2,9-diamino-substituted 1,10-phenanthrolines
• Amino-substituted-2,2 '-bis-1,10-phenanthroline

The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1H)-thione and 1,10-dihydro-1,10-phenanthroline-2,9-dithione have been accomplished. The sulfur-bridged bis-1,10-phenanthroline macrocycle was readily prepared by heating the thione or equimolar amounts of the dithione and 2,9-dichloro-1,10-phenanthroline in diphenyl ether. Displacements of 2-chloro- or 2,9-dichloro-1,10-phenanthroline with N,N-dimethylethylenediamine afforded the corresponding airline and diamino analogues. Am amino-substituted-2,2'-bis-1,10-phenanthroline has been prepared.

• 出版日期2009-7-1