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Abstract—Convenient and regioselective syntheses of 1,2-annulated, and 1,2-, 5,6- and 1,2-, 7,8-bisannulated polycyclic indolizine deriv- atives have been achieved by one-pot tandem reactions of cyclic N-ylides derived from the corresponding N-substituted pyridinium, quino- linium, and isoquinolinium salts 1–3 with dichloro substituted a,b-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. ? 2007 Elsevier Ltd. All rights reserved. |
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