Tetrahedron

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

…, YY Huang, KL Chen, JJ Huang, MY Yeh, FF Wong

Index: Chen, Chun-Yen; Lin, Hui-Chang; Huang, Yu-Ying; Chen, Kun-Lung; Huang, Jiann-Jyh; Yeh, Mou-Yung; Wong, Fung Fuh Tetrahedron, 2010 , vol. 66, # 10 p. 1892 - 1897

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Citation Number: 14

Abstract

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 ...