o-Quinonoid heterocycles: synthesis and crystal structure of 2,3-dicyano-5,7-bismethylthieno[3,4-b]pyrazine

Eva H Mørkved; Jon A Beukes; Frode Mo

doi:10.3390/12081623

o-Quinonoid heterocycles: synthesis and crystal structure of 2,3-dicyano-5,7-bismethylthieno[3,4-b]pyrazine

Molecules. 2007 Jul 30;12(8):1623-31. doi: 10.3390/12081623.

Authors

Eva H Mørkved¹, Jon A Beukes, Frode Mo

Affiliation

¹ Department of Chemistry, Norwegian University of Science and Technology, N-7491 Trondheim, Norway. eva.morkved@chem.ntnu.no

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) A at 100 K.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallization
Heterocyclic Compounds / chemical synthesis
Heterocyclic Compounds / chemistry*
Molecular Conformation
Pyrazines / chemical synthesis
Pyrazines / chemistry*
Thiophenes / chemical synthesis
Thiophenes / chemistry*
X-Ray Diffraction

Substances

2,3-dicyano-5,7-bismethylthieno(3,4-b)pyrazine
Heterocyclic Compounds
Pyrazines
Thiophenes