Sequential N‐Arylation and Intramolecular Imine Addition Reaction of Indoloazomethine Ylides with Arynes for the Synthesis of Thiadiazepine Derivatives

Metal‐free reaction of indoloazomethine ylides with 2‐(trimethylsilyl)aryl triflates in the presence of TMAF and MeOH provided 1,4‐thiadiazepines through sequential N‐arylation and intramolecular imine addition reaction, which is fully oxidized with p‐chloranil. These compounds are smoothly isomeriz...

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Published inAdvanced synthesis & catalysis Vol. 363; no. 5; pp. 1358 - 1367
Main Authors Kim, Dae Kyum, Son, Jeong‐Yu, Jung, Ilyong, Heo, Namrim, Han, Sang Hoon, Kim, Dongwook, Lee, Phil Ho
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 02.03.2021
Wiley Subscription Services, Inc
Subjects
Aromatic compounds
aryne
Chemistry
Chemistry, Applied
Chemistry, Organic
indoloazomethine ylide
metal-free
Physical Sciences
Science & Technology
thiadiazepine
TMAF
POTENT
aryne
SYDNONE DERIVATIVES
TMAF
thiadiazepine
indoloazomethine ylide
metal-free
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Summary:Metal‐free reaction of indoloazomethine ylides with 2‐(trimethylsilyl)aryl triflates in the presence of TMAF and MeOH provided 1,4‐thiadiazepines through sequential N‐arylation and intramolecular imine addition reaction, which is fully oxidized with p‐chloranil. These compounds are smoothly isomerized to indoloindolizines in quantitative yield. Moreover, formation of indoloindolizine was accessed from indoloazomethine ylide and 2‐(trimethylsilyl)aryl triflate in semi‐one‐pot.
Bibliography:Dedicated to Professor Shim Sung Lee (Gyeongsang National University) on the occasion of his retirememt.
D. K. Kim and J.‐Y. Son contributed equally to this work.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001310