Pyrazine Analogues of Dipyrrolylquinoxalines

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4141-4144

  Sessler, Jonathan L ^a   Pantos, G Dan ^a   Katayev, Evgeny ^a   Lynch, Vincent M ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZINE DERIVATIVE; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; DRUG SYNTHESIS; RECEPTOR BINDING; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRAZINES; PYRROLES; QUINOXALINES;

EID: 0345376250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0355635     Document Type: Article

References (16)

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2. Sorochinskii, V. V.; Kurganov, B. I. Appl. Biochem. Microbiol. 1997, 33, 579. Schreerder, J.; Engbersen, J. F. J.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1996, 115, 307.
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5. Sessler, J. L.; Davis, J. M. Acc. Chem. Res. 2001, 34, 989.
6. Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134. Kirkovits, G. J.; Zimmerman, R. S.; Huggins, M. T.; Lynch, V. M.; Sessler, J. L. Eur. J. Org. Chem. 2002, 3768.
7. Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134. Kirkovits, G. J.; Zimmerman, R. S.; Huggins, M. T.; Lynch, V. M.; Sessler, J. L. Eur. J. Org. Chem. 2002, 3768.
8. Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134. Kirkovits, G. J.; Zimmerman, R. S.; Huggins, M. T.; Lynch, V. M.; Sessler, J. L. Eur. J. Org. Chem. 2002, 3768.
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11. w = 0.1186 (all data), CCDC 217630. See the Supporting Information for CIF files.
12. Bucher, C.; Zimmerman, R. S.; Lynch, V.; Kral, V.; Sessler, J. L J. Am. Chem. Soc. 2001, 123, 2099. Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17.
13. Bucher, C.; Zimmerman, R. S.; Lynch, V.; Kral, V.; Sessler, J. L J. Am. Chem. Soc. 2001, 123, 2099. Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17.
14. Cotton, F. A.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 478.
15. 3Bpyrr = lithium pyrrolidinoborohydride was synthesized according to the literature; see: Thomas, L. S.; Collins, C. J.; Cuzens, J. R.; Spiciarich, D.; Goralski, C. T.; Singaram, B. J. Org. Chem. 2001, 66, 1999.
16. We performed molecular modeling calculations, using HyperChem, v7.1 in order to calculate the rotational barrier for the C2-C6 and C11-C12 bonds (numbering of the atoms is according with the X-ray structure). We used the di-tert-butyl analogues of both 7 and 8 so as to keep the calculations tractable. The PM3 semiempirical method in conjunction with the Conformation Search module was used to determine the structure with the minimum energy. The criteria for convergence was a difference in energy between two sequential structures below 0.01 kcal/(A mol). The results of these calculation show that the rotational barrier is 37% higher in the case of 8 vs 7. This is consistent with preorganization and conformation affects being significant aryl bridged dipyrrole anion receptors, and more so in the case of the larger dipyrrolylquinoxalines than in the smaller dipyrrolylpyrazines.