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Molecules 2007, 12(8), 1623-1631; doi:10.3390/12081623
Article

o-Quinonoid Heterocycles: Synthesis and Crystal Structure of 2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine

1,* , 2 and 2,*
Received: 1 June 2007; in revised form: 20 July 2007 / Accepted: 20 July 2007 / Published: 30 July 2007
(This article belongs to the Special Issue Heterocycles)
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Abstract: 2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine (5), has been obtained as a minor product from reactions of S-nucleophiles with 5,6-di(1-bromoethyl)pyrazine-2,3- dicarbonitrile (3), or from a condensation of 4-hydroxy-2,5-dimethyl-2,3-dihydrothiophen- 3-one (4) with diaminomaleonitrile. The molecular structure of compound 5 has been confirmed by X-ray diffraction. A partial separation of charge causes a donor-acceptor type arrangement of the planar molecules in uniform parallel stacks with an interplanar spacing of 3.334(2) Å at 100 K.
Keywords: Thieno[3; 4-b]pyrazine; o-quinonoid heterocycles; pyrazine-dicarbonitrile;di(1-bromoethyl)pyrazine; crystal structure. Thieno[3; 4-b]pyrazine; o-quinonoid heterocycles; pyrazine-dicarbonitrile; di(1-bromoethyl)pyrazine; crystal structure.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Mørkved, E.H.; Beukes, J.A.; Mo, F. o-Quinonoid Heterocycles: Synthesis and Crystal Structure of 2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine. Molecules 2007, 12, 1623-1631.

AMA Style

Mørkved EH, Beukes JA, Mo F. o-Quinonoid Heterocycles: Synthesis and Crystal Structure of 2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine. Molecules. 2007; 12(8):1623-1631.

Chicago/Turabian Style

Mørkved, Eva H.; Beukes, Jon A.; Mo, Frode. 2007. "o-Quinonoid Heterocycles: Synthesis and Crystal Structure of 2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine." Molecules 12, no. 8: 1623-1631.



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