铑（III）催化的酰亚胺 C-H 氨甲酰化和环化反应生成双环[1,3,5]三嗪酮。
Rh(III)-Catalyzed Imidoyl C-H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones.
机构信息
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
出版信息
Org Lett. 2020 Nov 20;22(22):8993-8997. doi: 10.1021/acs.orglett.0c03393. Epub 2020 Nov 10.
Abstract
A Rh(III)-catalyzed synthesis of bicyclic [1,3,5]triazinones from a diverse array of imines coupled with ethyl (pivaloyloxy)carbamate is reported. The preparation of [5,6]- and [6,6]-bicyclic heterocycles substituted with aryl, alkyl, and alkoxy groups demonstrated a broad reaction scope. The efficiency of this approach was further enhanced with the development of a three-component variant featuring in situ imine formation. X-ray crystallographic characterization of a rhodacycle formed by imidoyl C-H activation provides support for the proposed mechanism.
摘要
报道了一种通过 Rh(III)催化，从各种亚胺与乙基（特戊酰氧基）氨基甲酸酯的偶联反应中合成双环[1,3,5]三嗪酮的方法。该方法制备了取代基为芳基、烷基和烷氧基的[5,6]-和[6,6]-双环杂环，展示了广泛的反应范围。通过开发具有原位亚胺形成的三组分变体，进一步提高了该方法的效率。通过对亚胺酰基 C-H 活化形成的铑环的 X 射线晶体学表征，为所提出的机理提供了支持。
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