Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation

Ivan, Beatrice Cristina; Caira, Mino Rodolfo; Dumitrascu, Florea

Beatrice Cristina Ivan, Mino Rodolfo Caira, Florea Dumitrascu

Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation

Abstract:

The condensation of 1,4-benzoquinones with enamines reported ninety years ago is a name reaction known as the Nenitzescu indole synthesis which has proved to be a very useful method for obtaining both 5-hydroxyindoles and nonindole derivatives. An unexpected compound containing two condensed azepine rings was isolated in 1988 from the reaction between 1,4-benzoquinone and ethyl 3-aminocinnamate performed in 1-butanol. The reinvestigation of the proposed bisazepine structure by X-ray analysis revealed instead a pyrrole-azepine hybrid having the two heterocycles rings connected by a double bond.

Keywords:
Nenitzescu 5-hydroxyindole synthesis; X-ray diffraction; pyrrole; azepine

Issue: 2020, Volume 71, Issue 5

Pages: 51-57

Publication date: 2020/5/29

https://doi.org/10.37358/RC.20.5.8112

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
IVAN, B.C., CAIRA, M.R., DUMITRASCU, F., Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation, Rev. Chim., 71(5), 2020, 51-57.

Vancouver
Ivan BC, Caira MR, Dumitrascu F. Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation. Rev. Chim.[internet]. 2020 May;71(5):51-57. Available from: https://doi.org/10.37358/RC.20.5.8112

APA 6th edition
Ivan, B.C., Caira, M.R. & Dumitrascu, F. (2020). Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation. Revista de Chimie, 71(5), 51-57. https://doi.org/10.37358/RC.20.5.8112

Harvard
Ivan, B.C., Caira, M.R., Dumitrascu, F. (2020). 'Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation', Revista de Chimie, 71(5), pp. 51-57. https://doi.org/10.37358/RC.20.5.8112

IEEE
B.C. Ivan, M.R. Caira, F. Dumitrascu, "Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation". Revista de Chimie, vol. 71, no. 5, pp. 51-57, 2020. [online]. https://doi.org/10.37358/RC.20.5.8112

Text
Beatrice Cristina Ivan, Mino Rodolfo Caira, Florea Dumitrascu,
Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation,
Revista de Chimie,
Volume 71, Issue 5,
2020,
Pages 51-57,
ISSN 2668-8212,
https://doi.org/10.37358/RC.20.5.8112.
(https://revistadechimie.ro/Articles.asp?ID=8112)
Keywords: Nenitzescu 5-hydroxyindole synthesis; X-ray diffraction; pyrrole; azepine

RIS
TY - JOUR
T1 - Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation
A1 - Ivan, Beatrice Cristina
A2 - Caira, Mino Rodolfo
A3 - Dumitrascu, Florea
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2020
VL - 71
IS - 5
SP - 51
EP - 57
UR - https://doi.org/10.37358/RC.20.5.8112
KW - Nenitzescu 5-hydroxyindole synthesis
KW - X-ray diffraction
KW - pyrrole
KW - azepine
ER -

BibTex
@article{RevCh2020P51,
author = {Ivan Beatrice Cristina and Caira Mino Rodolfo and Dumitrascu Florea},
title = {Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation},
journal = {Revista de Chimie},
volume = {71},
number = {5},
pages = {51-57},
year = {2020},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.20.5.8112},
url = {https://revistadechimie.ro/Articles.asp?ID=8112}
}

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