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‘One-flask’ transformation of isocyanates and isothiocyanates to guanidines hydrochloride by using sodium bis(trimethylsilyl)amide |
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| Authors: | Chun-Yen Chen Yu-Ying Huang Jiann-Jyh Huang Fung Fuh Wong |
| Institution: | a Graduate Institute of Pharmaceutical Chemistry, China Medical University, No. 91, Hsueh-Shih Rd. Taichung, Taiwan 40402, ROC b Department of Chemistry, National Cheng Kung University, No. 1, Ta Hsueh Rd., Tainan, Taiwan 70101, ROC c Development Center for Biotechnology, No. 101, Lane 169, Kangning St., Xizhi City, Taipei County, Taiwan 221, ROC d Sustainable Environment Research Center, National Cheng Kung University, No 500, Sec. 3, An-ming Rd., Tainan City, Taiwan 709, ROC e Department of Resources Engineering, National Cheng Kung University, No 1, Ta Hsueh Rd., Tainan, Taiwan 70101, ROC |
| 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 isocyanates or isothiocyanates with sodium bis(trimethylsilyl)amide. Addition of amines and catalytic amount of AlCl3 smoothly converted the cyanamides to the desired guanidines. |
| Keywords: | Guanidines Isocyanates Isothiocyanates Cyanamides Sodium bis(trimethylsilyl)amide |
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