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

被引：0
|
作者：
Limjirawatthana, Suphaporn [1 ]
Ploypradith, Poonsakdi [1 ,2 ,3 ]
Ruchirawat, Somsak [1 ,2 ,3 ]
Theppitak, Chatphorn [1 ]
Ieawsuwan, Winai [1 ,2 ]
机构：
[1] Chulabhorn Res Inst, Lab Med Chem, 54 Kamphaeng Phet 6 Rd, Laksi 10210, Bangkok, Thailand
[2] Minist Higher Educ Sci Res & Innovat MHESI, Inst Off Permanent Secretary OPS, Ctr Excellence Environm Hlth & Toxicol EHT, Bangkok 10400, Thailand
[3] Chulabhorn Grad Inst, Program Chem Sci, 54 Kamphaeng Phet 6 Rd, Laksi 10210, Bangkok, Thailand
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2025年
关键词：
hypervalent iodine; ene-carbamate; tetrahydroisoquinoline; oxazol-2(3H)-one; acyliminium ion; INTERMOLECULAR ADDITION-REACTIONS; 7-OXYGENATED APORPHINE ALKALOIDS; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; 7-HYDROXYAPORPHINES; PROTOBERBERINE; (-)-EGENINE; ENAMINES; INDOLES; ACCESS;
D O I：
10.1002/asia.202401754
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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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页数：7
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