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Palladium-catalysed stereoselective [3 + 2] annulation of vinylethylene carbonates and tryptanthrin-based ketones
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-11-22 , DOI: 10.1039/d1qo01543e
Yang Fan 1, 2 , Qing-Zhu Li 2 , Jun-Long Li 2 , Bin Zhang 2 , Zhen Dai 2 , Ke Xie 2 , Rong Zeng 2 , Liang Zou 3 , Xiang Zhang 2
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The palladium-catalysed [3 + 2] annulation of vinylethylene carbonates (VECs) and ketones remains challenging in organic synthesis. Herein, we successfully achieved the [3 + 2] annulation of tryptanthrin-based ketones and VECs for the efficient synthesis of indoloquinazolinone derivatives with generally excellent yields and good diastereoselectivity. Notably, the asymmetric version of this [3 + 2] annulation can also be achieved by using a chiral spiroketal-based diphosphine ligand. In addition, preliminary biological studies reveal that some of the products exhibit promising antibacterial activity.

中文翻译:

钯催化立体选择性 [3 + 2] 乙烯基碳酸亚乙酯和色氨酸基酮的环化

钯催化的 [3 + 2] 乙烯基碳酸亚乙酯 (VEC) 和酮的环化在有机合成中仍然具有挑战性。在此,我们成功地实现了基于色胺酮的酮和 VEC 的 [3 + 2] 环化,用于高效合成吲哚喹唑啉酮衍生物,并且通常具有优异的收率和良好的非对映选择性。值得注意的是,这种 [3 + 2] 环化的不对称形式也可以通过使用基于手性螺缩酮的二膦配体来实现。此外,初步的生物学研究表明,一些产品表现出有希望的抗菌活性。
更新日期:2021-11-30
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