Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides,The Journal of Organic Chemistry

当前位置： X-MOL 学术 › J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-09-13 , DOI: 10.1021/acs.joc.1c01552
Andrey Bubyrev ₁ , Maria Adamchik ₁ , Dmitry Dar'in ₁ , Grigory Kantin ₁ , Mikhail Krasavin ₁

Affiliation

A new type of diazo compounds, namely, CH-diazomethane sulfonamides (generated in situ from readily available α-acetyl-α-diazomethane sulfonamides), was employed in a 1,3-dipolar cycloaddition reaction with imines (also formed in situ from primary amines and aldehydes). The reaction gave hitherto undescribed 1,5-disubstituted 1,2,3-triazoline-4-sulfonamides, which were obtained in good to excellent yields with complete trans diastereoselectivity. These new sulfonamides based on the nonaromatic 1,2,3-triazoline core are rather attractive from a medicinal chemistry standpoint in light of the strong emphasis recently put on the nonflat, more saturated (higher Fsp3) scaffolds for lead-generation libraries. The oxidative aromatization of 1,2,3-triazoline-4-sulfonamides by manganese(IV) oxide gave nearly quantitative yields of 1,2,3-triazole-4-sulfonamides, of which only two examples have been reported in the literature.

中文翻译：

1,2,3-三唑啉-4-磺酰胺的无金属三组分合成

一种新型的重氮化合物，即 CH-重氮甲烷磺酰胺（由容易获得的 α-乙酰基-α-重氮甲烷磺酰胺原位生成），用于与亚胺的 1,3-偶极环加成反应（也原位形成）来自伯胺和醛）。该反应产生了迄今为止未描述的 1,5-二取代的 1,2,3-三唑啉-4-磺酰胺，其以良好至极好的产率获得，具有完全的反式非对映选择性。这些基于非芳香族 1,2,3-三唑啉核心的新型磺胺类药物从药物化学的角度来看相当有吸引力，因为最近非常重视用于铅生成文库的非平坦、更饱和（更高的 Fsp3）支架。通过氧化锰 (IV) 对 1,2,3-三唑啉-4-磺酰胺的氧化芳构化产生了几乎定量的 1,2,3-三唑-4-磺酰胺，文献中仅报道了其中两个例子。

更新日期：2021-10-01

点击分享查看原文

点击收藏

阅读更多本刊最新论文