Isothiocyanate intermediates facilitate divergent synthesis of N-heterocycles for DNA-encoded libraries

Chemical Communications, Год журнала: 2024, Номер 60(59), С. 7638 - 7641

Опубликована: Янв. 1, 2024

DNA-compatible diversity-oriented synthesis of nitrogen-containing heterocycles via the in situ conversion primary amines into versatile isothiocyanates intermediates.

Язык: Английский

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DNA-Compatible Huisgen [3 + 2] Cycloaddition of In Situ Formed Nitrile Oxides with Alkenes or Alkynes to Synthesize Isoxazolines or Isoxazoles

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 13, 2025

DNA-encoded chemical library (DECL) technology is recognized as a robust screening platform for drug discovery. Developing new DNA-compatible reactions crucial expanding the space of DECLs. Cyclization reactions, particularly those involving formation heterocycles, offer unique and efficient methods accessing privileged scaffolds or lead-like small molecules. In this study, we introduce two that utilize readily accessible aldehydes to create substituted isoxazolines isoxazoles by 1,3-dipolar cycloaddition reaction. These demonstrate high conversion efficiency can be applied wide range substrates. The are do not cause significant DNA degradation.

Язык: Английский

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DNA-Compatible N-Formylation of Amines by Using TMSCF₂Br

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 15, 2025

DNA-encoded libraries (DELs) have emerged as powerful tools in drug discovery. Protected amino acids serve essential building blocks the construction of DELs, resulting widespread presence groups within these libraries. N-formylation free amines not only enhances activity lead compounds but also functions an effective amino-protecting strategy. In this study, we introduce trimethyl(bromodifluoromethyl)silane (TMSCF2Br) a novel reagent for DEL synthesis. This approach demonstrates robustness DEL-compatible synthesis and enables library diversification through functional group transformation (FGT). Additionally, achieved efficient removal formyl groups, enabling to be strategically used on-DNA protection orthogonal Fmoc Boc groups.

Язык: Английский

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Photoinduced Site-Selective Alkylation Enabling Synthesis of C-3-Alkylated Quinoxalinone on DNA

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 30, 2025

A mild and biocompatible strategy for the site-selective alkylation of quinoxalinones via photoinduced dehydrogenative has been developed. This protocol enables functionalization both unprotected quinoxalinone nonreactive dihydroquinoxalinone under DNA-compatible conditions. The optimized reaction proceeds efficiently while tolerating a diverse range alkyl donors from various radical precursors. Given its simplicity DNA compatibility, this methodology offers platform construction DNA-encoded libraries incorporating privileged scaffold.

Язык: Английский

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Electrochemical synthesis of 2-amino-1,3,4-oxadiazoles via TBAI-mediated desulfurative cyclization of isothiocyanates and hydrazines

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134746 - 134746

Опубликована: Май 1, 2025

Язык: Английский

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