O- and N-alkylated diketopyrrolopyrrole derivatives

Tetrahedron Letters

Volumn 52, Issue 44, 2011, Pages 5769-5773

  Frebort, Štěpán ^a,b   Eliáš, Zdeněk ^a,c   Lyčka, Antonín ^b   Luňák Jr , Stanislav ^a   Vyňuchal, Jan ^c   Kubáč, Lubomir ^a,b   Hrdina, Radim ^a   Burgert, Ladislav ^a  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

^b Centre for Organic Chemistry Ltd   (Czech Republic)

^c Synthesia As   (Czech Republic)

Author keywords

1,4 Diketo pyrrolo 3,4 c pyrroles; Alkylation; NMR; O Alkyl

Indexed keywords

ALKYL GROUP; PYRROLE DERIVATIVE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; ISOLATION PROCEDURE; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80054974892     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.113     Document Type: Article

References (26)

1. Iqbal, A.; Cassar, L. EP 98808, 1984;
2. Chem. Abstr. 1984, 100, 176461.
3. Herbst, W.; Hunger, K. Industrial Organic Pigments; Wiley-VCH: Weinheim, 2004. pp 489.
4. (a) Potrawa, T.; Langhals, H. Chem. Ber. 1987, 120, 1075;
5. (b) Lange, G.; Tieke, B. Macromol. Chem. Phys. 1999, 200, 106-112;
6. (c) Tieke, B.; Beyerlein, T. Macromol. Rapid Commun. 2000, 21, 182-189;
7. (d) Colonna, G.; Pilati, T.; Rusconi, F.; Zecchi, G. Dyes Pigments 2007, 75, 125-129.
8. (a) Tamayo, A. B.; Dang, X. D.; Walker, B.; Seo, J.; Kent, T.; Nguyen, T. Q. Appl. Phys. Lett. 2009, 94, 103301;
9. (b) Yuan, M.; Rice, A. H.; Luscombe, Ch. K. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 701-711;
10. (c) Chen, G.-Y.; Chiang, Ch.-M.; Kekuda, D.; Lan, S.-C.; Chu, C.-W.; Wei, K.-H. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1669-1675.
11. Qu, S.; Wu, W.; Hua, J.; Kong, C.; Long, Y.; Tian, H. J. Phys. Chem. C 2010, 114, 1343-1349.
12. (a) Vala, M.; Weiter, M.; Vyňuchal, J.; Toman, P.; Luňak, S., Jr. J. Fluoresc. 2008, 18, 1181-1186;
13. (b) Qu, Y.; Hua, J.; Tian, H. Org. Lett. 2010, 12, 3320-3323.
14. Iqbal, A.; Jost, M.; Kirchmayr, R.; Pfenninger, J.; Rochat, A.; Wallquist, O. Bull. Soc. Chim. Belg. 1988, 97, 615-643.
15. Stas, S.; Sergeyev, S.; Geerts, Y. Tetrahedron 2010, 66, 1837-1845.
16. Zabicky, J. The Chemistry of Amides; Intersicience Publishers: London, 1970. pp 159.
17. Avcibasi, N.; Smet, M.; Metten, B.; Dehaen, W.; De Schryver, F. C.; Bultynck, G.; Callewaert, G.; De Smedt, H.; Missiaen, L.; Boens, N. Int. J. Photoenergy 2004, 6, 159-167.
18. (a) Luňak, S., Jr.; Vyňuchal, J.; Vala, M.; Havel, L.; Hrdina, R. Dyes Pigments 2009, 82, 102-108;
19. (b) Luňak, S., Jr.; Havel, L.; Vyňuchal, J.; Horakova, P.; Kučerik, J.; Weiter, M.; Hrdina, R. Dyes Pigments 2010, 85, 27-36;
20. (c) Luňak, S., Jr.; Vyňuchal, J.; Horačkova, P.; Frumarova, B.; Žak, Z.; Kučerik, J.; Salyk, O. J. Mol. Struct. 2010, 983, 39-47.
21. Berger, S.; Braun, S. 200 and More NMR Experiments. A Practical Course; Wiley-VCH: Weinheim, 2004.
22. Kalinowski, H. O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: Chichester, 1988.
23. The B3LYP hybrid xc functional in combination with the 6-311G(d,p) basis set was used for geometry optimization. The excitation energies in DMSO were computed using the PCM (polarized continuum model) TD (time dependent) DFT (B3LYP/6-311+G(2d,p)) methodology on the above described ground state geometries.
24. Gaussian 09, Revision A.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian; Inc. Wallingford, CT, 2009.
25. (a) Tamayo, A. B.; Tantiwiwat, M.; Walker, B.; Nguyen, T. Q. J. Phys. Chem. C 2008, 112, 15543;
26. (b) Burckstummer, H.; Weissenstein, A.; Bialas, D.; Wurthner, F. J. Org. Chem. 2011, 76, 2426.