Development of heterocyclic compounds using various active species containing selenium

含有多个活性位点的化合物是制备杂环化合物非常有用的原料。然而，使用硒化合物如硒脲、硒酰胺、硒偶氮二烯和硒化乙炔的应用报告数量有限。近年来，我们开发了硒脲、硒酰胺、硒偶氮二烯和乙炔硒化物的制备方法。我们研究了利用各种含硒活性物质开发杂环化合物。以硒偶氮二烯为原料，与氯乙腈反应得到1,3-硒唑-5-碳腈，与氯乙酰氯和胺反应得到1,3-硒唑-5-羧酰胺，与卤酮反应得到5-酰基-2-氨基-1,3-硒唑。以硒脲为原料，与氯乙腈反应得到2-氨基-1,3-硒唑-4-氯化亚胺，与酮或醛反应得到2-氨基-1,3-硒唑。以异硒氰酸酯为原料，制备了1,2,4-三唑、1,3-硒化氮杂化、1,3-硒化氮杂化、1,3-硒化氮杂化和1-噻亚-6-氧- 6ab ^4-硒-3-氮杂二烯。因此，我们证实了具有多个活性位点的硒化合物是制备新型杂环化合物的优良起始材料。

Compounds bearing multiple active sites are very useful as starting materials for heterocyclic compounds. However, there are limited number of reports of applications using selenium compounds such as selenourea, selenoamide, selenazadiene, and acetylene selenide. Recently, we developed methods for the preparation of selenourea, selenoamide, selenazadiene, and acetylene selenide. We have investigated development of heterocyclic compounds using the various active species containing selenium. Using selenazadiene, reactions with chloroacetonitrile gave 1,3-selenazole-5-carbonitrile, reactions with chloroacetoyl chloride and amine gave 1,3-selenazole-5-carboxylamide, reactions with haloketone gave 5-acyl-2-amino-1,3-selenazole, respectively. Using selenourea, reactions with chloroacetonitrile gave 2-amino-1,3-selenazol-4-iminium chloride, reactions with ketone or aldehyde afforded 2-amino-1,3-selenazole. Using isoselenocyanate, 1,2,4-triazole, 1,3-selenazetizine, 1,3-selenazole, 1,3-selenazine and 1-thia-6-oxa-6aλ^4-seleno-3-azapentalene were prepared.Thus we have confirmed that selenium compounds bearing multiple active sites are excellent starting materials for preparation of novel heterocyclic compounds.