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Photochemical Functionalization of 4-Diazoisoquinoline-1,3(2H,4H)-diones and Their 1-Sulfoxide Analogues

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Isoquinoline-1,3(2 H,4 H )-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 H,4 H )-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.

Source: ACS Organic & Inorganic Au

DOI: 10.1021/acsorginorgau.5c00017

Authors: Joseph P. Milton, Dorota Gryko

Institutions: Institute of Organic Chemistry, Polish Academy of Sciences

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funder: H2020 Marie Skłodowska-Curie Actions