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

Authors(10) :-Mitsunori Oda, Satoshi Ito, Yosuke Fukuchi, Shun Kato, Yurie Fujiwara, Yoshimitsu Kumai, Kosuke Ariyasu, Akira Ohta, Shigeyasu Kuroda, Ryuta Miyatake

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.

Authors and Affiliations

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

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

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Publication Details

Published in : Volume 2 | Issue 3 | May-June 2016
Date of Publication : 2016-06-30
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 424-435
Manuscript Number : IJSRSET1623117
Publisher : Technoscience Academy

Print ISSN : 2395-1990, Online ISSN : 2394-4099

Cite This Article :

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.
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