Hypervalent Iodine(III)‐Mediated Oxidative Cyclization of <i>Exo</i>‐Cyclic Ene‐Carbamate to Tetrahydroisoquinoline‐Oxazol‐2(3<i>H</i>)‐one Derivatives

The new development of a transition-metal-free method for the synthesis of THIQ-oxazol-2(3H)-one motif from exo-cyclic ene-carbamates by using hypervalent iodine as an oxidant is reported. Various functional groups substituted on the aryl rings of the ene-carbamate substrates as well as the N- and S-heterocyclic substrates afforded the corresponding THIQ-oxazol-2(3H)-one products in up to 91 % yield. Moreover, the synthetic utility was highlighted for the synthesis of phthalide-THIQ natural product, (±)-corlumine.

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Publication Details

Journal
Chemistry - An Asian Journal
Published
2025-02-26
DOI
https://doi.org/10.1002/asia.202401754
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
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article

Hypervalent Iodine(III)‐Mediated Oxidative Cyclization of Exo‐Cyclic Ene‐Carbamate to Tetrahydroisoquinoline‐Oxazol‐2(3H)‐one Derivatives

Winai Ieawsuwan, Chatphorn Theppitak, Somsak Ruchirawat, Poonsakdi Ploypradith et al.
Chemistry - An Asian Journal
Oxidative Organic Chemistry Reactions
article

Hypervalent Iodine(III)‐Mediated Oxidative Cyclization of Exo‐Cyclic Ene‐Carbamate to Tetrahydroisoquinoline‐Oxazol‐2(3H)‐one Derivatives

Winai Ieawsuwan, Chatphorn Theppitak, Somsak Ruchirawat, Poonsakdi Ploypradith, Suphaporn Limjirawatthana
article en

Abstract

The new development of a transition-metal-free method for the synthesis of THIQ-oxazol-2(3H)-one motif from exo-cyclic ene-carbamates by using hypervalent iodine as an oxidant is reported. Various functional groups substituted on the aryl rings of the ene-carbamate substrates as well as the N- and S-heterocyclic substrates afforded the corresponding THIQ-oxazol-2(3H)-one products in up to 91 % yield. Moreover, the synthetic utility was highlighted for the synthesis of phthalide-THIQ natural product, (±)-corlumine.

Chemistry - An Asian JournalVol. 20(10)
Chulabhorn Graduate Institute (TH), Chulabhorn Research Institute (TH), Office of the Higher Education Commission (TH)
Openalex Percentile: Top 97%
Oxidative Organic Chemistry Reactions
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