Reaction of tetracyanoethylene with diselenium dichloride: a route to pyrrolo[2,3-c][1,2,6]selenadiazines

文献情報

出版日 2023-12-13

DOI 10.1039/D3NJ04876D

インパクトファクター 3.591

著者

Cory Laurent, Andreas Kourtellaris, Panayiotis A. Koutentis

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要旨

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%).

掲載誌

New Journal of Chemistry

CiteScore: 5.3

自己引用率: 3.7%

年間論文数: 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.

Reaction of tetracyanoethylene with diselenium dichloride: a route to pyrrolo[2,3-c][1,2,6]selenadiazines

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New Journal of Chemistry

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