Synthesis and Mechanistic Study of Cyclic Oxoguanidines via Zn(OTf)2‐Catalyzed Guanylation/Amidation from Readily Available Amino Acid Esters and Carbodiimides |
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| Authors: | Yue Chi Ling Xu Shanshan Du Haihan Yan Prof Dr Wen‐Xiong Zhang Prof Dr Zhenfeng Xi |
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| Institution: | 1. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (P. R. China), Fax: (+86)?10‐62751708;2. State Key Laboratory of Elemento‐Organic Chemistry, Nankai University, Tianjin 300071 (P. R. China) |
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| Abstract: | The Zn(OTf)2‐catalyzed guanylation/amidation from readily available amino acid esters and carbodiimides is achieved to provide efficiently various cyclic oxoguanidines, including 2‐amino‐1H‐imidazol‐5(4H)‐ones and 2‐aminoquinazolin‐4(3H)‐ones in medium‐to‐high yields. It is the first time that an ammonium salt has been used in a guanylation reaction. The application of cyclic oxoguanidines to provide the conjugated heterocyclic compounds via oxidative C?N formation or aldol reaction is explored. The reaction mechanism is well elucidated by the isolation and characterization of three important intermediates. |
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| Keywords: | amino acid esters carbodiimides cyclic oxoguanidines cyclization guanylation |
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