Novel Synthetic Methods for Disubstituted Pyrroles from Pyrrolidine and 2-Substituted 1-Pyrrolines

Authors

  • Mitsunori Oda  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Satoshi Ito  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Yosuke Fukuchi  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Shun Kato  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Yurie Fujiwara  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Yoshimitsu Kumai  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Kosuke Ariyasu  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Akira Ohta  Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano, Japan
  • Shigeyasu Kuroda  Graduate School of Science and Engineering for Education, University of Toyama, Gofuku 3190, Toyama, Japan
  • Ryuta Miyatake  Centre for Environmental Conservation and Research Safety, University of Toyama, Gofuku 3190, Toyama, Japan

Keywords:

Pyrroles, Pyrrolidine, 1-Pyrrolines, Pyrrolophanes, Indoles, Dipyrrins

Abstract

Development of facile synthetic methods for various disubstituted pyrroles from pyrrolidine and 2-substituted 1-pyrrolines is reviewed based on our recent findings. Various 1,3-disubstituted pyrroles were synthesized by reaction of pyrrolidine and aldehyde heating without any catalyst. On the other hand, 2,3-disubstituted pyrroles were synthesized from 2-substituted 1-pyrrolines by a sequece involving its aldol-type condensation with aldehyde and subsequent base-catalyzed double-bond isomerization. Application of the former method to one-pot synthesis of a pyrrolocyclophane and preparation of N-substituted indoles from indoline and aldehydes is disclosed. Some pyrrole products by the latter method were transformed into dipyrrin derivatives via their pyrrole-2-carbaldehydes, and chemical and structural properties of the dipyrrin derivatives are described.

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International Journal of Scientific Research in Science, Engineering and Technology

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2016-06-30

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Volume 2, Issue 3, May-June-2016

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Mitsunori Oda, Satoshi Ito, Yosuke Fukuchi, Shun Kato, Yurie Fujiwara, Yoshimitsu Kumai, Kosuke Ariyasu, Akira Ohta, Shigeyasu Kuroda, Ryuta Miyatake, " Novel Synthetic Methods for Disubstituted Pyrroles from Pyrrolidine and 2-Substituted 1-Pyrrolines, International Journal of Scientific Research in Science, Engineering and Technology(IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 2, Issue 3, pp.424-435, May-June-2016.