Rhodium‐Catalyzed (3+3) Cascade Cyclization of Diazobarbiturates with 2H‐Azirines for the Diastereoselective Construction of Spirooxazinopyrimidinediones

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-06-25 DOI:10.1002/ejoc.202500551

Hong-Wu Zhao, Yue Zhang, Yu-Hang Mi, Kuo Wang, Zhi-Yu Wang, Jin-Tao Li

引用次数: 0

Abstract

Under the catalysis of Rh2(esp)2 (10 mol%) and BINAP (20 mol%) in 1,2‐dichloroethane at 80 °C, a (3+3) cascade cyclization between diazobarbiturates and 2H‐azirines proceeded smoothly, yielding spirooxazinopyrimidinediones in 24‐92% yield with >20:1 diastereoselectivity. The chemical structure of one compound has been confirmed by X‐ray diffraction analysis, and the others are suggested by inference.

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铑催化重氮巴比妥酸盐与2H -氮嘧啶的（3+3）级联环化，用于螺恶嗪嘧啶嘧啶二酮的非对映选择性构建

在Rh2(esp)2 （10 mol%）和BINAP （20 mol%）在1,2‐二氯乙烷中80℃催化下，重氮巴比妥酸盐和2H‐氮嘧啶之间的（3+3）级联环化反应顺利进行，产率为24‐92%，非对构选择性为20:1。其中一种化合物的化学结构已通过X射线衍射分析得到证实，其他化合物的化学结构是通过推理得到的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.