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Issue 42, 2016
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Intramolecular oxyacetoxylation of N-allylamides: an expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride–pyridine system

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Abstract

The synthesis of oxazolines and oxazines from N-allylamides was accomplished via an unprecedented reaction set. This reaction involved an intramolecular cyclization of N-allylamides resulting from nucleophilic attack of the allylamine on the benzoxazin-4-one. Unlike the previous literature, the isolable N-allylamide could readily be subjected to exo and endo fashion ring-closure under conditions to afford the title compounds.

Graphical abstract: Intramolecular oxyacetoxylation of N-allylamides: an expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride–pyridine system

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Publication details

The article was received on 12 Aug 2016, accepted on 01 Oct 2016 and first published on 04 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01752E
Citation: Org. Biomol. Chem., 2016,14, 10074-10079
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    Intramolecular oxyacetoxylation of N-allylamides: an expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride–pyridine system

    J. Ranjith, N. Rajesh, B. Sridhar and P. Radha Krishna, Org. Biomol. Chem., 2016, 14, 10074
    DOI: 10.1039/C6OB01752E

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