Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles

A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90–120°C, 5–13h). Thermodynamically controlled E/Z-isomer ratio of 1-styryl...

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Published in:Tetrahedron 2012-02, Vol.68 (7), p.1963-1971
Main Authors: Dvorko, Marina Yu, Schmidt, Elena Yu, Glotova, Tatyana E., Shabalin, Dmitrii A., Ushakov, Igor' A., Kobychev, Vladimir B., Petrushenko, Konstantin B., Mikhaleva, Al'bina I., Trofimov, Boris A.
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Language:English
Subjects:
Analogs
Isomerization
Nucleophilic addition
Pyrroles
Stilbene
Styrylpyrroles
Superbase
Synthesis (chemistry)
Tetrahedrons
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cited_by cdi_FETCH-LOGICAL-c330t-611980eff92cb36f530faa114bc807d065b8da44ec5772eee1ca8e2b37bed7f33
cites cdi_FETCH-LOGICAL-c330t-611980eff92cb36f530faa114bc807d065b8da44ec5772eee1ca8e2b37bed7f33
container_end_page 1971
container_issue 7
container_start_page 1963
container_title Tetrahedron
container_volume 68
creator Dvorko, Marina Yu
Schmidt, Elena Yu
Glotova, Tatyana E.
Shabalin, Dmitrii A.
Ushakov, Igor' A.
Kobychev, Vladimir B.
Petrushenko, Konstantin B.
Mikhaleva, Al'bina I.
Trofimov, Boris A.
description A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90–120°C, 5–13h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole—phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole—phenylacetylene and 2-(2-thienyl)pyrrole—phenylacetylene, respectively). [Display omitted]
doi_str_mv 10.1016/j.tet.2011.12.050
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source ScienceDirect Freedom Collection
subjects Analogs
Isomerization
Nucleophilic addition
Pyrroles
Stilbene
Styrylpyrroles
Superbase
Synthesis (chemistry)
Tetrahedrons
title Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles
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