REGIO- AND STEREOSELECTIVE SYNTHESIS OF NITROFUNCTIONALIZED 1,2-OXAZOLIDINE ANALOGS OF NICOTINE

Authors

  • Agnieszka Fryźlewicz Cracov University of Technology, Depertment of Organic Chemistry, 31-155 Cracov
  • Agnieszka Łapczuk-Krygier Cracov University of Technology, Depertment of Organic Chemistry, 31-155 Cracov
  • Karolina Kula Cracov University of Technology, Depertment of Organic Chemistry, 31-155 Cracov
  • Oleg M. Demchuk Pharmaceutical Research Institute, 8 Rydygiera St., 01-793 Warsaw
  • Ewa Dresler Institute of Heavy Organic Synthesis “Blachownia”, 9 Energetyków St., 47-225 Kędzierzyn-Koźle
  • Radomir Jasiński Cracov University of Technology, Depertment of Organic Chemistry, 31-155 Cracov

DOI:

https://doi.org/10.1007/5404

Keywords:

nicotine analogs, nitroalkenes, nitrones, 1, 2-oxazolidines, [3 2] cycloaddition.

Abstract

(E)-3,3,3-Trichloro-1-nitroprop-1-ene undergoes [3+2] cycloaddition reaction with N-aryl(pyridin-3-yl) nitrones under mild conditions. The reaction is fully regio- and stereoselective and gives expected nitro-substituted nicotine analogs with 3,4-cis-4,5-trans-stereoconfiguration.

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Published

2020-01-31

Issue

Vol. 56 No. 1 (2020)

Section

Short Communications