Synthesis of Indole-Fused Dihydrothiopyrano Scaffolds via (3+3)- Annulations of Donor-Acceptor Cyclopropanes with Indoline-2-Thiones

被引：17
|
作者：
Gopal, Braj [1 ]
Singh, Prasoon Raj [1 ]
Kumar, Madan [1 ]
Goswami, Avijit [1 ]
机构：
[1] Indian Inst Technol Ropar, Dept Chem, Rupnagar 140001, Punjab, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
关键词：
FORMAL 3+3 CYCLOADDITION; ORGANOSULFUR COMPOUNDS; MERCAPTOACETALDEHYDE; 1,1-DIESTERS; BRASSILEXIN; ANALOGS; SCOPE;
D O I：
10.1021/acs.joc.2c01990
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new methodology for the synthesis of N-haloindole-fused dihydrothiopyrano derivatives via (3 + 3) -annulation of donor-acceptor cyclopropanes (DACs) with indoline-2-thiones in the presence of Sc(OTf)3 as a Lewis acid catalyst has been developed. This protocol provides a variety of indole-fused dihydrothiopyrano molecules in good to excellent yields, which architecturally resemble other indole-fused tricyclic molecules having potential medicinal value. In addition, we have described a detailed reaction mechanism and transformation of the furnished product into N-fused thiazino indole molecule.
引用
收藏
页码：132 / 142
页数：11
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