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

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

1,* , 2 and 2,*
1 Department of Chemistry, Norwegian University of Science and Technology, N-7491 Trondheim, Norway 2 Department of Physics, Norwegian University of Science and Technology, N-7491 Trondheim, Norway
* Authors to whom correspondence should be addressed.
Received: 1 June 2007 / Revised: 20 July 2007 / Accepted: 20 July 2007 / Published: 30 July 2007
(This article belongs to the Special Issue Heterocycles)
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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 (CC BY 3.0).

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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.

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