Reaction of tetracyanoethylene with diselenium dichloride: a route to pyrrolo[2,3-c][1,2,6]selenadiazines
Literature Information
Publication Date
2023-12-13
DOI
10.1039/D3NJ04876D
Impact Factor
3.591
Authors
Cory Laurent, Andreas Kourtellaris, Panayiotis A. Koutentis
View Original
Abstract
Tetracyanoethylene reacts with Se2Cl2, SO2Cl2 and catalytic BnEt3NCl in 1,2-dichloroethane heated at ca. 70 °C for 40 h to give 4,6-dichloropyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile (42%) and 4-chloro-6-oxo-6,7-dihydropyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile (30%). A chromatography free procedure allows isolation of 4,6-dichloropyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile in 70% yield. Regioselective displacement of the 6-chloro by O- and N-nucleophiles is demonstrated. Treatment of 4-chloro-6-morpholinopyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile with morpholine gives a low yield of the 4,6-dimorpholinopyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile (8%) together with 2,5-dimorpholino-3-oxo-3H-pyrrole-4-carbonitrile (13%) and 3,5-dimorpholino-2-oxo-2H-pyrrole-4-carbonitrile (55%).
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Source Journal
New Journal of Chemistry
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5.3
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3.7%
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2153
NJC (New Journal of Chemistry) is a broad-based primary journal encompassing all branches of chemistry and its sub-disciplines. It contains full research articles, communications, perspectives and focus articles. This well-established journal, owned by the Centre National de la Recherche Scientifique (CNRS) of France, has been co-published with the Royal Society of Chemistry since January 1998. NJC is the forum for the publication of high-quality, original and significant work that opens new directions in chemistry or other scientific disciplines. In addition to having a significant chemical component, work published in NJC must demonstrate that it will have an impact on areas of research other than that of the reported work.
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