4.4 Article

First I2-K2CO3-promoted sequential C-N and C-O bond forming approach for one-pot synthesis of 1,4-benzoxazines

Journal

TETRAHEDRON LETTERS
Volume 54, Issue 52, Pages 7132-7135

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.10.092

Keywords

Iodine; One-pot reaction; alpha-Haloketones; beta-Aminoalcohol; 1,4-Benzoxazines

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I-2-K2CO3 combination has been found to be an efficient, reusable, and inexpensive catalyst system for the one-pot synthesis of 3-aryl-2H-benz[1,4]oxazine via rapid C=N and C-O bond formation. No by-product formation, operational simplicity, ambient temperature, and high yield (85-94%) are the attractive features of the envisaged reaction. The reported one-pot synthesis of 1,4-benzoxazine involves the application of I-2-K2CO3 catalyst system for the first time and proceeds via in situ imine formation followed by intramolecular ring transformation cascades. (C) 2013 Elsevier Ltd. All rights reserved.

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