Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to beta-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea

An efficient, PhI(OAc)(2)-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-on...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 52; no. 16; pp. 2395 - 2409
Main Authors Du, Yiming, Chen, Yue, Liu, Yun-Lin, Qin, Weiwei, Li, Zhaodong
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 18.08.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
radical
AZIDO
ARYLATION
difunctionalization
UNACTIVATED ALKENES
transition-metal-free
OLEFINS
DIAZIDATION
domino
QUINOXALIN-2(1H)-ONES
DERIVATIVES
azide
AZIDOARYLATION
ARYLAMINES
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Summary:An efficient, PhI(OAc)(2)-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-one derivatives and could be extended to phosphinyl-alkylated quinoxalin-2(1H)-one in a single step in moderate to excellent yields under mild conditions, as demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time. Mechanistic studies revealed that this transformation undergoes a cascade addition pathway controlled by a polar radical.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707514