Synthesis ( IF 2.2 ) Pub Date : 2018-02-27 , DOI: 10.1055/s-0037-1609304 Kamil Kabala 1 , Barbara Grzeszczyk 1 , Bartłomiej Furman 1 , Marek Chmielewski 1 , Jolanta Solecka 2 , Adam Guśpiel 2
|
Abstract
The Kinugasa reaction between phthalimidoacetylene and cyclic nitrones derived from l-phenylglycine or l-serine and glyoxylic acid, catalyzed by copper(I) chloride in the presence of triethylamine, is reported. The acetylene molecule approaches the nitrone exclusively anti to the bulky substituent next to the nitrogen atom to provide the cis-substituted β-lactam ring preferentially. The six-membered oxazinone ring can be easily opened, the phthaloyl residue can be transformed into a Boc protecting group, and substituents at the C-4 carbon atom and the nitrogen atom of the β-lactam ring can be easily removed or transformed into groups suitable for further synthesis of a variety of monobactam structures. Selected synthesized compounds were evaluated for their biological activity, showing interesting properties.
The Kinugasa reaction between phthalimidoacetylene and cyclic nitrones derived from l-phenylglycine or l-serine and glyoxylic acid, catalyzed by copper(I) chloride in the presence of triethylamine, is reported. The acetylene molecule approaches the nitrone exclusively anti to the bulky substituent next to the nitrogen atom to provide the cis-substituted β-lactam ring preferentially. The six-membered oxazinone ring can be easily opened, the phthaloyl residue can be transformed into a Boc protecting group, and substituents at the C-4 carbon atom and the nitrogen atom of the β-lactam ring can be easily removed or transformed into groups suitable for further synthesis of a variety of monobactam structures. Selected synthesized compounds were evaluated for their biological activity, showing interesting properties.
中文翻译：
通过非对映选择性Kinugasa反应合成Monobactams
摘要
据报道，在三乙胺存在下，氯化亚铜催化了邻苯二甲酰亚胺乙炔与衍生自1-苯基甘氨酸或1-丝氨酸的环硝酮与乙醛酸之间的Kinugasa反应。乙炔分子接近硝酮专门抗到大体积取代基旁边的氮原子以提供顺-取代的β-内酰胺环优先。六元恶嗪酮环可轻松打开，邻苯二甲酰基残基可转化为Boc保护基，β-内酰胺环的C-4碳原子和氮原子上的取代基可轻松除去或转化为基团适用于进一步合成多种单bactam结构。评价了选定的合成化合物的生物活性，显示出令人感兴趣的特性。
据报道，在三乙胺存在下，氯化亚铜催化了邻苯二甲酰亚胺乙炔与衍生自1-苯基甘氨酸或1-丝氨酸的环硝酮与乙醛酸之间的Kinugasa反应。乙炔分子接近硝酮专门抗到大体积取代基旁边的氮原子以提供顺-取代的β-内酰胺环优先。六元恶嗪酮环可轻松打开，邻苯二甲酰基残基可转化为Boc保护基，β-内酰胺环的C-4碳原子和氮原子上的取代基可轻松除去或转化为基团适用于进一步合成多种单bactam结构。评价了选定的合成化合物的生物活性，显示出令人感兴趣的特性。
京公网安备 11010802027423号