The first synthesis of pyridinium N-benzoylguanidines by bismuth- and mercury-promoted guanylation of N-iminopyridinium ylide with thioureas
- 作者：Silvio Cunha ; Manoel T. Rodrigues ; Jr. ; Cleuza C. da Silva ; Hamilton B. Napolitano ; Ivo Vencato and Carlito Lariucci
- 关键词：Pyridinium ; Guanidine ; Bismuth
- 刊名：Tetrahedron
- 出版年：2005
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：2005
- 卷：61
- 期：44
- 页码：10536-10540
- 文件大小：183 K
摘要
This work describes the first successful synthesis of five pyridinium N-benzoylguanidines. These new pyridinium ylides were prepared in moderate to good yields through the guanylation reaction of N-iminopyridinium ylide with N-benzoylthioureas, using both bismuth nitrate and mercury chloride as inorganic thiophiles. X-ray analysis of one pyridinium N-benzoylguanidine was investigated and the E configuration assigned. Intermolecular interactions of the type C–H
O and C–Hπ were observed in the solid state. The results related in this study represent the first description of a ylide as the nucleophilic partner in the guanylation reaction.
O and C–Hπ were observed in the solid state. The results related in this study represent the first description of a ylide as the nucleophilic partner in the guanylation reaction.