Abstract:
:Brønsted acid-induced fragmentation of a triazoline is used as a tool to identify Brønsted base additives capable of playing the role of a proton shuttle. Relative to water, dimethyl formamide accelerates proton transfer substantially under these conditions. A series of alcohols and ethers were also used to demonstrate that the Brønsted basicity of additive functionality, not their Brønsted acidity, is responsible for their ability to accelerate proton transfer from triazoline N3 to N1. This knowledge was then used to develop a convenient two step protocol for the synthesis of oxazolidine diones from benzyl azide and an unsaturated imide that employs a substoichiometric additive for triazolinium fragmentation.
journal_name
Bioorg Med Chem Lettjournal_title
Bioorganic & medicinal chemistry lettersauthors
Donahue MG,Hong KB,Johnston JNdoi
10.1016/j.bmcl.2009.07.067subject
Has Abstractpub_date
2009-09-01 00:00:00pages
4971-3issue
17eissn
0960-894Xissn
1464-3405pii
S0960-894X(09)01032-4journal_volume
19pub_type
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