砜亚胺导向的钌催化（杂）芳烃的邻位C-H烯基化反应：EP3受体拮抗剂类似物的合成

Sulfoximine-directed ruthenium-catalyzed ortho-C-H alkenylation of (hetero)arenes: synthesis of EP3 receptor antagonist analogue.

作者信息

Yadav M Ramu, Rit Raja K, Shankar Majji, Sahoo Akhila K

机构信息

School of Chemistry, University of Hyderabad , Hyderabad 500046, India.

出版信息

J Org Chem. 2014 Jul 3;79(13):6123-34. doi: 10.1021/jo5008465. Epub 2014 Jun 24.

DOI:10.1021/jo5008465

PMID:24905413

Abstract

The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and α,β-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.

摘要

展示了可重复使用的亚砜亚胺导向基团辅助的Ru(II)催化的芳烃和杂芳烃与丙烯酸酯以及α,β-不饱和酮/乙烯基砜的化学和区域选择性邻位C-H烯基化反应。N-芳酰基亚砜亚胺与二苯乙炔发生环化反应，生成异喹啉酮和甲基苯亚砜。本方法成功用于合成EP3受体拮抗剂类似物。