Milton Joseph P, Gryko Dorota
Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw 01-224, Poland.
ACS Org Inorg Au. 2025 Mar 24;5(3):205-210. doi: 10.1021/acsorginorgau.5c00017. eCollection 2025 Jun 4.
Isoquinoline-1,3-(2,4)-diones have been the subject of numerous studies toward new pharmaceuticals, and therefore novel, mild functionalizations of this scaffold are highly desirable. As diazo compounds are versatile reagents in organic synthesis, 4-diazoisoquinoline-1,3-(2,4)-diones should give access to a broad range of various derivatives. Indeed, they enable the introduction of fluorinated moieties via photochemical O-H insertion reactions in serviceable yields, typically in under 2 h. Exchanging the 1-carbonyl group with the sulfoxide moiety causes a hypsochromic shift in the absorption of the diazo compounds, and thus, violet light is required for effective O-H and S-H insertion reactions.
异喹啉 -1,3-(2,4)-二酮一直是众多新型药物研究的主题，因此，对该骨架进行新颖、温和的官能化是非常必要的。由于重氮化合物是有机合成中的多功能试剂，4-重氮异喹啉 -1,3-(2,4)-二酮应该能够得到各种各样的衍生物。事实上，它们能够通过光化学O - H插入反应以可观的产率引入氟化部分，通常在2小时内即可完成。用亚砜部分取代1 - 羰基会导致重氮化合物吸收发生蓝移，因此，有效的O - H和S - H插入反应需要紫光。
