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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 3, pp 339–343 | Cite as

(Aza)indolizines and ethyl propiolate: [8+2] and [1,10] cyclizations

  • Eugene V. BabaevEmail author
  • Ivan A. Shadrin
  • Viktor B. Rybakov
Article

(Aza)indolizines reacted with ethyl propiolate regioselectively forming (aza)[2.2.3]cyclazines. The Sonogashira reaction of 5-iodo(aza)-indolizines and acetylenes led to 5-ethynyl(aza)indolizines. In the case of indolizine derivative the by-product was ethynylcyclazine. The structures of [2.2.3]cyclazines were proved by X-ray structural analysis.

Keywords

imidazo[1,2-a]pyridine indolizine [8+2] cycloaddition Sonogashira reaction 

Notes

The authors are grateful to Thermo Fisher Scientific Inc., MS Analitika (Moscow), and personally to Prof. A. A. Makarov for providing the mass spectrometric equipment used in this work

The work was carried out using the equipment (STOE STADIVARI Pilatus 100K diffractometer) purchased under the Moscow State University development program.

Supplementary material

10593_2018_2270_MOESM1_ESM.pdf (402 kb)
ESM 1 (PDF 402 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Eugene V. Babaev
    • 1
    Email author
  • Ivan A. Shadrin
    • 1
  • Viktor B. Rybakov
    • 1
  1. 1.Lomonosov Moscow State UniversityMoscowRussia

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