4.4 Article

Iodine-mediated electrophilic cyclization of 2-alkynylbenzaldoximes leading to the formation of iodoisoquinoline N-oxides

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 38, Pages 5531-5533

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.07.061

Keywords

electrophilic cyclization; iodonium ion; iodine; isoquinoline N-oxide; 2-alkynylbenzaldoxime; isoquinoline

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Reaction of 2-alkynylbenzaldoximes 1 with 5 equiv of iodine in EtOH at room temperature gives the corresponding iodoisoquinoline N-oxides 2 in good to excellent yields. The cyclization proceeds very smoothly and quickly without any additives such as bases under very mild reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.

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