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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Bibliographic Details
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.
Format: Article
Language:English
Subjects:
Analogs
Isomerization
Nucleophilic addition
Pyrroles
Stilbene
Styrylpyrroles
Superbase
Synthesis (chemistry)
Tetrahedrons
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Summary: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]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.12.050