Journal
TETRAHEDRON
Volume 63, Issue 9, Pages 2024-2033Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.12.050
Keywords
annulated indolizines; pyridinium ylides; quinolinium ylides; isoquinolinium ylides; [3+2] cycloadditions
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Convenient and regioselective syntheses of 1,2-annulated, and 1,2-, 5,6- and 1,2-, 7,8-bisannulated polycyclic indolizine derivatives have been achieved by one-pot tandem reactions of cyclic N-ylides derived from the corresponding N-substituted pyridinium, quinolinium, and isoquinolinium salts 1-3 with dichloro substituted alpha,beta-unsaturated carbonyl compounds 4-7. The reactions of the N-ylides with 2,3-dichloroindenone 4, 3,4-dichlorocoumarin 5, and 4a,6,7,8a-tetrachloro-1,4-methanonaphthalene-5,8-dione 6 proceed by sequential [3+2] cycloaddition and elimination of hydrogen chlorides from the cycloadducts. On the other hand, reactions of the N-ylides with 2,3-dichloro-1,4-naphthoquinone 7 take place via a novel reaction sequence to give the products 15-17. (c) 2007 Elsevier Ltd. All rights reserved.
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