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

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-30 DOI:10.1021/acs.orglett.5c01236

Kyeong Seop Kim, Junseok Ra, Madala Hari Babu, Eunbin Jang, Seohyeon Kang, Minhyeok Yoo, Thinh T. M. Bui, Kyuho Moon, Jaehoon Sim

引用次数: 0

Abstract

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

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光诱导选择性烷基化在DNA上合成c -3-烷基化喹啉酮

提出了一种温和的、生物相容性良好的喹诺啉酮光诱导脱氢烷基化的位点选择性烷基化策略。该方案使未受保护的喹诺沙林酮和非反应性的二氢喹诺沙林酮在dna相容条件下功能化。优化后的反应可以有效地进行，同时可以耐受来自不同自由基前体的各种烷基给体。鉴于其简单性和DNA兼容性，该方法为构建包含特权喹诺沙林酮支架的DNA编码文库提供了平台。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.