Modular Preparation of 5‑Halomethyl-2-oxazolines via PhI(OAc)2‑Promoted Intramolecular Halooxygenation of N‑Allylcarboxamides

A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)­benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-11, Vol.80 (22), p.11339-11350
Main Authors: Liu, Gong-Qing, Yang, Chun-Hua, Li, Yue-Ming
Format: Article
Language:English
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Summary:A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)­benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading to the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in good to excellent isolated yields. The 5-halomethyl products could be converted to different derivatives via conventional nucleophilic substitution methods. The reactions were carried out using easily available starting materials, and did not need harsh reaction conditions. All these features made this reaction a viable method for the construction of different oxazoline and thiazoline structures.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01832