Efficient synthesis of 5-substituted 2-aryl- 6-cyanoindolizines via nucleophilic substitution reactions

• Eugene V. Babaev,
• Natalya I. Vasilevich and
• Anna S. Ivushkina

Beilstein J. Org. Chem. 2005, 1, No. 9, doi:10.1186/1860-5397-1-9

• -chloroindolizines readily underwent nucleophilic substitution at position 5 leading in high yields to novel 5-functionalised indolizines. Keywords: 5-chloroindolizine; 5-substituted indolizines; 5-indolizinone; nucleophilic substitution; Indolizines are an important class of heterocyclic compounds since many

• natural alkaloids contain in their structure a saturated (swainsonine) or aromatic (camptothecin) indolizine moiety. While the chemistry of indolizines has been widely investigated[1] the chemistry of 5-substituted indolizines remains very poor because there are only a few reliable ways for their

• products in good yields.[3] An interesting method for preparing 5-substitutied indolizines by recyclization of oxazolo[3,2-a]pyridinium salts was developed in our laboratory.[4][5] Using this strategy a series of 5-substituted indolizines have been prepared in good yields, but (although the method seems to