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.
Authors
- Winai Ieawsuwan (ORCID: https://orcid.org/0000-0001-8587-2972)
- Chatphorn Theppitak (ORCID: https://orcid.org/0000-0003-2091-4937)
- Somsak Ruchirawat (ORCID: https://orcid.org/0000-0001-5842-4330)
- Poonsakdi Ploypradith (ORCID: https://orcid.org/0000-0003-2893-1598)
- Suphaporn Limjirawatthana
Institutions
- Chulabhorn Graduate Institute (TH)
- Chulabhorn Research Institute (TH)
- Office of the Higher Education Commission (TH)
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
- Field-Weighted Citation Impact
- 0.00