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Synthesis 2000; 2000(12): 1733-1737
DOI: 10.1055/s-2000-8195
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A Novel and Practical Synthesis of 3-Unsubstituted Indolizines

Lande Zhang* , Feng Liang, Lingzhi Sun, Yuefei Hu, Hongwen Hu
  • *Department of Chemistry, Nanjing University, Nanjing 210093, People's Republic of China
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Publication Date:
31 December 2000 (online)

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A novel and practical procedure for the preparation of 3-unsubstituted indolizines by 1,3-dipolar cycloaddition was developed. The requisite pyridinium N-methylides were generated simply from the corresponding N-(carboxymethyl)pyridinium halides. In the presence of MnO2, electron-deficient alkenes, instead of alkynes or vinyl bromides, were used successfully as dipolarophiles. This general method features cheap reagents, simple workup procedure and gives the products in moderate to high yields (57-92%).

cycloadditions - dehydrogenation - manganese dioxide - heterocycles