title: Synthesis and Mechanistic Study of Cyclic Oxoguanidines via Zn(OTf)2 -Catalyzed Guanylation/Amidation from Readily Available Amino Acid Esters and Carbodiimides.
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.
authors.affiliation: 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.
authors.forename: Yue
authors.initials: Y
authors.lastname: Chi
authors.affiliation: 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.
authors.forename: Ling
authors.initials: L
authors.lastname: Xu
authors.affiliation: 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.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Du
authors.affiliation: 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.
authors.forename: Haihan
authors.initials: H
authors.lastname: Yan
authors.affiliation: 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. wx_zhang@pku.edu.cn.|State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P. R. China). wx_zhang@pku.edu.cn.
authors.forename: Wen-Xiong
authors.initials: WX
authors.lastname: Zhang
authors.affiliation: 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.
authors.forename: Zhenfeng
authors.initials: Z
authors.lastname: Xi
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000634:Aminoquinolines / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000634:Aminoquinolines; D002234:Carbodiimides; D004952:Esters; D006146:Guanidines; D006571:Heterocyclic Compounds; D007093:Imidazoles; D008698:Mesylates; C117197:imidazolone; C012077:trifluoromethanesulfonic acid
keywords: amino acid esters; carbodiimides; cyclic oxoguanidines; cyclization; guanylation