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

Molecules

Volumn 12, Issue 8, 2007, Pages 1623-1631

  Mørkved, Eva H ^a   Beukes, Jon A ^a   Mo, Frode ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

Author keywords

Crystal structure; Di(1 bromoethyl)pyrazine; o quinonoid heterocycles; Pyrazine dicarbonitrile; Thieno 3,4 b pyrazine

Indexed keywords

2,3 DICYANO 5,7 BISMETHYLTHIENO(3,4 B)PYRAZINE; 2,3-DICYANO-5,7-BISMETHYLTHIENO(3,4-B)PYRAZINE; HETEROCYCLIC COMPOUND; PYRAZINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; SYNTHESIS; X RAY DIFFRACTION;

CRYSTALLIZATION; HETEROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; PYRAZINES; THIOPHENES; X-RAY DIFFRACTION;

EID: 34548391832     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12081623     Document Type: Article

References (17)

1. Mørkved, E.H.; Wang, C. Preparation and Reactions of 5,6-Bis(bromomethyl)pyrazine-2,3-dicarbonitrile with S, N and O Nucleophiles. Synthesis of Octa(propoxymethyl) Azaphthalocyaninato Magnesium. J. Prakt. Chem. 1997, 339, 473-476.
2. Büchi, G.; Demole, E.; Thomas, A.F. Syntheses of 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (Furaneol), a Flavor Principle of Pineapple and Strawberry. J. Org. Chem. 1973, 38, 123-125.
3. Eru, E.; Hawkes, G.E.; Utley, J.H.P.; Wyatt, P.B. Electro-organic Reactions. Part 41. Diels-Alder Reactions of o-Quinodimethanes from the Cathodic Reduction of ∀,∀'-Dibromo-1,2-dialkylbenzenes. Tetrahedron 1995, 51, 3033-3044.
4. Bieniarz, C.; Cornwell, M.J. A Facile, High-Yielding Method for the Conversion of Halides to Mercaptans. Tetrahedron. Lett. 1993, 34, 939-942.
5. King, B.; Demole, E.; Thomas, A.F. 4-Hydroxy-2,5-dimethyl-2,3- dihydrothiophen-3-one, useful as flavouring. Ger. Offen. 1972, 14pp. 2, 214, 540.
6. [Chem. Abstr. 1973, 78, 29615a].
7. Van den Ouweland, G.A.M.; Peer, H.G. Furan and thiophenes containing meat-like flavour components. Ger. Offen. 1970, 91 pp. 1, 932, 800.
8. [Chem. Abstr. 1970, 72, 90265d].
9. Outurquin, F.; Paulmier, C. Synthèse de nouveaux systèmes hétérocycliques thiophéniques azotés à partir du diamino-3,4-thiophène. Bull. Soc. Chim. Fr. 1983, II 159-163.
10. Thomas, K.R.J.; Lin, J.T.; Tao, Y-T.; Chuen, C-H. Star-Shaped Thieno-[3,4-b]-Pyrazines: A New Class of Red-Emitting Electroluminescent Materials. Adv. Mater. 2002, 14, 822-826.
11. Pohmer, J.; Lakshmikantham, M.V.; Cava, M.P. Synthesis of Thieno[3,4-b]quinoxaline and Derivatives. J. Org. Chem. 1995, 60, 8283-8288.
12. Aqad, E.; Lakshmikantham, M.V.; Cava, M.P.; Metzger, R.M. Intramolecular Charge-Transfer Interactions in B-Extended Tetrathiafulvalene Derivatives. J. Org. Chem. 2005, 70, 768-775.
13. Kenning, D.D.; Mitchell, K.A.; Calhoun, T.R.; Funfar, M.R.; Sattler, D.J.; Rasmussen, S.C. Thieno[3,4-b]pyrazines: Synthesis, Structure, and Reactivity. J. Org. Chem. 2002, 67, 9073-9076.
14. Kitamura, C.; Tanaka, S.; Yamashita, Y. Synthesis of New Narrow Bandgap Polymers Based on 5,7-Di(2-thienyl)thieno[3,4-b]pyrazine and its Derivatives. J. Chem. Soc., Chem. Commun. 1994, 1585-1586.
15. International Tables for Crystallography, Vol. C, Prince, E., Ed.; Kluwer: Dordrecht, 2004; Chap. 9.5; pp. 799-806.
16. Pierson, H.O. Handbook of Carbon, Graphite, Diamond and Fullerenes: Properties, Processing and Applications. Noyes Publications: Park Ridge, New Jersey, 1993; pp. 44-46, 58-61.
17. Sheldrick, G.M. SHELX-97 - Programs for Crystal Structure Analysis Release 97-2; University of Göttingen: Göttingen, Germany, 1997.