‘One-flask’ transformation of isocyanates and isothiocyanates to guanidines hydrochloride by using sodium bis(trimethylsilyl)amide

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• 作者：Chun-Yen Chen ; Hui-Chang Lin ; Yu-Ying Huang ; Kun-Lung Chen ; Jiann-Jyh Huang ; Mou-Yung Yeh ; Fung Fuh Wong
• 关键词：Guanidines ; Isocyanates ; Isothiocyanates ; Cyanamides ; Sodium bis(trimethylsilyl)amide
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：6 March 2010
• 年：2010
• 卷：66
• 期：10
• 页码：1892-1897
• 全文大小：557 K

文摘

A ‘one-flask’ synthesis of guanidines was developed by reacting isocyanates and isothiocyanates with sodium bis(trimethylsilyl)amide followed by addition of primary or secondary amines with a catalytic amount of AlCl₃. The desired guanidines were obtained in good yields and the reaction was applicable to aliphatic and aromatic substrates. A plausible mechanism was proposed through the generation of cyanamide anion from isocyanates or isothiocyanates with sodium bis(trimethylsilyl)amide. Addition of amines and catalytic amount of AlCl₃ smoothly converted the cyanamides to the desired guanidines.