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Sc(OTf)3-catalyzed tandem (3+3)-annulation/lactonization of cyclopropanes with salicylaldehyde nitrones to access polycyclic 1,2-oxazines
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2024-01-07 , DOI: 10.1002/jhet.4775
Zhiping Liu 1 , Jie Pang 1 , Lijie Che 1 , Liping Pang 1 , Chunfang Gan 1 , Jianguo Cui 1 , Yanmin Huang 1
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A Sc(OTf)3-catalyzed tandem (3 + 3)-annulation/lactonization of donor-acceptor cyclopropane 1,1-dieters with salicylaldehyde nitrones has been reported, affording a wide range of tetrahydrochromeno[4,3-c][1,2]oxazin-5(1H)-ones in moderate yields with excellent diastereoselectivities. Besides, the gram-scale reaction has also been explored to demonstrate the utility of this protocol. Moreover, the mechanism was investigated through control experiments, which show the reaction proceeds via a tandem (3 + 3)-annulation/lactonization reaction.

中文翻译:

Sc(OTf)3-催化环丙烷与水杨醛硝酮的串联 (3+3)-环化/内酯化反应生成多环 1,2-恶嗪

据报道,Sc(OTf) 3催化供体-受体环丙烷 1,1-二酯与水杨醛硝酮的串联 (3 + 3) 成环/内酯化反应,可产生多种四氢色烯[4,3- c ][1 ,2]恶嗪-5(1 H )-酮,产率适中,具有优异的非对映选择性。此外,还探索了克级反应来证明该方案的实用性。此外,通过对照实验研究了该机理,结果表明该反应是通过串联 (3 + 3)-环化/内酯化反应进行的。
更新日期:2024-01-07
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