4.4 Article

Synthesis of highly functionalized oxazines by Vilsmeier cyclization of amidoalkyl naphthols

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 39, Pages 5474-5478

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.07.051

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Funding

  1. UGC
  2. CSIR (New Delhi)

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The intramolecular cyclization of amidoalkyl naphthols by Vilsmeier reagent produced 1,3-oxazines. The Vilsmeier reagent (chloromethylenedimethylammonium chloride) has been used as an efficient and cheap acid activator for the one-step synthesis of oxazine derivatives. A mechanism involving sequential haloformylation and intramolecular nucleophilic cyclization is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

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