252-01-7Relevant articles and documents
On the utility of the azido transfer protocol: Synthesis of 2- And 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole - azole bisheteroaryls
Zanirato, Paolo,Cerini, Stefano
, p. 1508 - 1513 (2007/10/03)
The azido transfer procedure of heteroaryllithium and tosyl azide was used to synthesize selected 2- and 5-azidoazoles. This procedure, which is based on the fragmentation of the appropriate lithium triazene salts 1a-7a, successfully afforded 2-azido-N-methylimidazole 1, 2-azido-l,3-thiazole 2, 2-azidobenzo-1.3-thiazole 3, 5-azido-N-methylpyrazole 4, 5-azido-N- methylimidazole 6 [via 2-(trimethylsilyl)-5-azido-N-methylimidazole 5], and 5-azido-l,3-thiazole 7 (via 5-lithio-1,3-thiazole), but attempts to prepare 5-azido-2-(trimethylsilyl)-1,3-thiazole 8 from the corresponding triazene 7a failed, affording only the desilylated azide 7 in poor yield. Azidcs 1-7 underwent 1,3-dipolar cycloaddition when mixed with neat (trimethylsilyl) acetylene, giving 1-heteroaryl-4-trimethylsilyl-1,2.3-triazoles 1b-7b generally in very high yields. The Royal Society of Chemistry 2005.