6-Dialkylaminobenzimidazole nonlinear optical dyes

Synthetic Communications

Volumn 42, Issue 18, 2012, Pages 2664-2675

  Davis, Matthew C ^a   Groshens, Thomas J ^a  

^a NAVAL AIR WARFARE CENTER   (United States)

Author keywords

Benzimidazole; Chromophore; Nonlinear optical

Indexed keywords

6 DIALKYLAMINOBENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; HYDROGENATION; MELTING POINT;

EID: 84861995497     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.564342     Document Type: Article

References (26)

1. Hales, J. M.; Matichak, J.; Barlow, S.; Ohira, S.; Yesudas, K.; Brédas, J.-L.; Perry, J. W.; Marder, S. R. Design of polymethine dyes with large third-order optical nonlinearities and loss figures of merit. Science 2010, 327, 1485-1488.
2. Melikian, G.; Rouessac, F. P.; Alexandre, C. Synthesis of substituted dicyanomethylendihydrofurans. Synth. Commun. 1995, 25, 3045-3051.
3. Dachlauer, K. Verfahren zur herstellung von trichloracetonitril. German Patent 694,479, December 25, 1937.
4. Bonham, J. A.; Petrellis, P. C. Chromophore-substituted vinyl-halomethyl-s-triazines. U.S. Patent 3,987,037, October 19, 1976.
5. Greizerstein, W.; Brieux, J. A. The ortho:para ratio in the activation of the nucleophilic aromatic substitution by the nitro group. J. Am. Chem. Soc. 1962, 84, 1032-1036.
6. Suzuki, K.; Ohtaka, H.; Ozaki, A.; Morimoto, Y.; Sukamoto, T. Benzimidazole derivative, process for preparing the same, antiemetic agent containing the same as active ingredient, and intermediate compound for preparing the same. U.S. Patent 5.407,936, April 18, 1995.
7. Kuş, C. Synthesis of new substituted 6-(morpholin-4-yl)-1H- benzimidazole derivatives. Turk. J. Chem. 2002, 26, 559-564.
8. Baek, J.-B.; Harris, F. W. Development of an improved synthetic route to an AB phenylquinoxaline monomer. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 801-814. (Pubitemid 40206675)
9. Illig, C. R.; Chen, J.; Wall, M. J.; Wilson, K. J.; Ballentine, S. K.; Rudolph, M. J.; Des Jarlais, R. L.; Chen, Y.; Schubert, C.; Petrounia, I.; Crysler, C. S.; Molloy, C. J.; Chaikin, M. A.; Manthey, C. L.; Player, M. R.; Tomczuk, B. E.; Meegalla, S. K. Discovery of novel FMS kinase inhibitors as anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2008, 18, 1642-1648. (Pubitemid 351343803)
10. Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. Facile method for the synthesis of combinatorial libraries of benzimidazole, benzothiazole, benzoxazole, permidine, and quinazolinone. Chin. J. Chem. 2009, 27, 379-383.
11. Tertov, B. A.; Koblik, A. V. Formylation of 1-methylbenzimidazole. Chem. Heterocycl. Compd. 1967, 3, 870-871.
12. Katritzky, A. R.; He, H.-Y.; Long, Q.; Cui, X.; Level, J.; Wilcox, A. L. The preparation of some heteroaromatic and aromatic aldehydes. Arkivoc 2000, 3, 240-251. (Pubitemid 40224614)
13. Asakawa, K.; Dannenberg, J. J.; Fitch, K. J.; Hall, S. S.; Kadowski, C.; Karaday, S.; Kii, S.; Maeda, K.; Marcune, B. F.; Mase, T.; Miller, R. A.; Reamer, R. A.; Tschaen, D. M. Why are benzimidazoles efficiently acylated with esters? Identification of a tetrahedral hemiacetal alkoxide intermediate. Tetrahedron Lett. 2005, 46, 5081-5084. (Pubitemid 40840668)
14. Plater, M. J.; Barnes, P.; McDonald, L. K.; Wallace, S.; Archer, N.; Gelbrich, T.; Horton, P. N.; Hursthouse, M. B. Hidden signatures: New reagents for developing latent fingerprints. Org. Biomol. Chem. 2009, 7, 1633-1641.
15. Sauvetre, R.; Roux-Schmitt, M.-C.; Seyden-Penne, J. Factors controlling the regioselectivity of additions to α-enones, VI. Tetrahedron 1978, 34, 2135-2140.
16. Deschamps, B. Factors controlling the regioselectivity of additions to α-enones, VII. Tetrahedron 1978, 34, 2009-2013.
17. 13C-retinal. Can. J. Chem. 1985, 63, 1431-1435.
18. Chen, Y. L.; Hedberg, K.; Guarino, K.; Retsema, J. A.; Anderson, M.; Manousos, M.; Barrett, J. (6R,8S)-(2-Benzimidazolyl)hydroxymethylpenicillanic acids as potent antibacterial agents and b-lactamase inhibitors. J. Antibiotics 1991, 44, 870-884.
19. 1H NMR utilization of through-space effects in configurational assignments, I: Application to nitriles; determination of the separate effects of the field and anisotropy of the CN group. Org. Magn. Res. 1980, 13, 323-327.
20. Ji, Y.-H.; Bur, D.; Häsler, W.; Schmitt, V. R.; Dorn, A.; Bailly, C.; Waring, M. J.; Hockstrasser, R.; Leupin, W. Tris-benzimidazole derivatives: Design, synthesis, and DNA sequence recognition. Bioorg. Med. Chem. 2001, 9, 2905-2919.
21. Dietrich, S. A.; Lindauer, R.; Stierlin, C.; Gertsch, J.; Matesanz, R.; Notararigo, S.; Diaz, J. F.; Altmann, K.-H. Epothilone analogues with benzimidazole and quinoline side chains: Chemical synthesis, antiproliferative activity, and interactions with tubulin. Chem. Eur. J. 2009, 15, 10144-10157.
22. Yamamoto, H.; Maruoka, K. Regioselective carbonyl amination using diisobutylaluminum hydride. J. Am. Chem. Soc. 1981, 103, 4186-4194.
23. Boykin, D. W.; Göker, H. Ring cleavage of dicyano-substituted benzimidazoles by DIBAL. Heterocycl. Commun. 2001, 7, 529-534. (Pubitemid 33675038)
24. Solchinger, A.; Wurst, K.; Kopacka, H.; Bildstein, B. Supramolecular stabilization of hemiacetals of N-alkyl(benz)imidazole aldehydes. Cryst. Growth Dev. 2007, 7, 2380-2381.
25. Davis, M. C.; Chafin, A. P.; Hollins, R. A.; Baldwin, L. C.; Erickson, E. D.; Zarras, P.; Drury, E. C. Synthesis of an isophorone-based nonlinear optical chromophore. Synth. Commun. 2004, 34, 3419-3429. (Pubitemid 39363358)
26. Wakabayashi, K.; Tsunoda, M.; Suzuki, Y. Studies on s-triazines, I: Cotrimerization of trichloroacetonitrile with other nitriles. Bull. Chem. Soc. Jpn 1969, 42, 2924-2930.