Preparation of new imidazol-2-yl-(amino)methylphosphonates, phosphinates and phosphine oxides and their unexpected cleavage under acidic conditions

详细信息    查看全文

• 作者：Bogdan Boduszek ; Tomasz K. Olszewski ; ^{tomasz.olszewski@pwr.wroc.pl} ; Waldemar Goldeman ; Kamila Grzegolec ; Patrycja Blazejewska
• 关键词：Imidazole ; Aminophosphonates ; Heterocycles ; Imines ; Cleavage
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：28 January, 2012
• 年：2012
• 卷：68
• 期：4
• 页码：1223-1229
• 全文大小：500 K

文摘

The efficient synthesis of new imidazol-2-yl-(amino)methylphosphonic acids, phosphonates phosphinate esters and phosphine oxides is described. The synthetic methodology is based on nucleophilic addition of phosphorus species to imidazole-2 derived imines. Additionally, it was discovered that heating the imidazol-2-yl-(amino)methylphosphonates with aqueous HCl or H₂SO₄ leads to their decomposition resulting in a rupture of the C-P bond, elimination of the phosphorous-containing fragment and formation of the corresponding secondary imidazole-2 alkylamines. A mechanistic pathway for the cleavage is postulated.