o-quinonoid heterocycles synthesis and crystal structure of 2,3-dicyano-5,7-bismethylthieno[3,4-b]pyrazineo-quinonoid杂环化合物的合成及晶体结构的3-dicyano-5,7-bismethylthieno[3、4 b]吡嗪.pdfVIP

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o-quinonoid heterocycles synthesis and crystal structure of 2,3-dicyano-5,7-bismethylthieno[3,4-b]pyrazineo-quinonoid杂环化合物的合成及晶体结构的3-dicyano-5,7-bismethylthieno[3、4 b]吡嗪.pdf

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o-quinonoid heterocycles synthesis and crystal structure of 2,3-dicyano-5,7-bismethylthieno[3,4-b]pyrazineo-quinonoid杂环化合物的合成及晶体结构的3-dicyano-5,7-bismethylthieno[3、4 b]吡嗪

Molecules 2007, 12, 1623-1631 molecules ISSN 1420-3049 © 2007 by MDPI /molecules Full Paper o-Quinonoid Heterocycles: Synthesis and Crystal Structure of 2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine Eva H. Mørkved 1,*, Jon A. Beukes 2 and Frode Mo 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; E-mail: eva.morkved@chem.ntnu.no or frode.mo@ntnu.no Received: 1 June 2007; in revised form: 20 July 2007 / Accepted: 20 July 2007 / Published: 30 July 2007 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. Introduction Several years ago we reported studies on 5,6-bis(bromomethyl)pyrazine-2,3