Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

被引：1
|
作者：
Kikuchi, Jun [1 ]
Nakajima, Roi [1 ]
Yoshikai, Naohiko [1 ]
机构：
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, 6-3 Aoba,Aramaki,Aoba ku, Sendai 9808578, Japan
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷
关键词：
alkynes; azoles; cross-coupling; hypervalent iodine; STEREOSELECTIVE-SYNTHESIS; PYRAZOLES; REGIO; VINYL; ARYL;
D O I：
10.3762/bjoc.20.79
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereoselective N -alkenylation of azoles with alkynes and iodine(III) electrophile is reported. The reaction between various azoles and internal alkynes is mediated by benziodoxole triflate as the electrophile in a trans -fashion, affording azole-bearing vinylbenziodoxoles in moderate to good yields. The tolerable azole nuclei include pyrazole, indazole, 1,2,3-triazole, benzotriazole, and tetrazole. The iodanyl group in the product can be leveraged as a versatile synthetic handle, allowing for the preparation of hitherto inaccessible types of densely functionalized N -vinylazoles.
引用
收藏
页码：891 / 897
页数：7
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