Journal
TETRAHEDRON
Volume 58, Issue 25, Pages 5023-5038Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)00469-6
Keywords
iodine heterocycles; pyrones; isocoumarins; Stille coupling; palladium catalysis
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5-Iodo-2(2H)-pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH2Cl2 or C6H6 at 20degreesC (Method C) or by treatment of these esters with ICl in CH2Cl2 at 20degreesC (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2H)-pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
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