Thianaphthene-Annulated Tetrapyrazinoporphyrazines

Ekaterina S. Taraymovich,^a@ Yulia Yu. Enakieva,^b Yulia V. Mitasova,^a and Pavel A. Stuzhin^a@

^aIvanovo State University of Chemistry and Technology, Ivanovo, 153000, Russia

^bFrumkin Institute of Physical Chemistry and Elecrochemistry RAS, Moscow, 119991, Russia

^@Corresponding authors E-mail: stuzhin@isuct.ru, taraimoviches@bk.ru

DOI: 10.6060/mhc2010.1.48

Macroheterocycles 2010 3(1) 48-50

Tetrapyrazinoporphyrazine with fused thianaphthene fragments, i.e. tetra(benzo[4’,5’]thieno[2’,3’:5,6]pyrazino[2,3-b,g,l,q]porphyrazine, [H2TSNpPyzPA], and its tetra-tert-butyl-substituted derivative, [H2TSNpPyzPAtBu4], having enhanced solubility in organic solvents, have been prepared by cyclotetramerization in a melt of corresponding benzo[4,5]thieno[2,3-b]pyrazine-2,3-dicarbonitriles obtained by condensation of diaminomaleodinitrile with 2,3-thianaphthenquinones [2,3-dihydrobenzo[b]thiophene-2,3-diones] easily available by acylation of thiophenols with oxalylchloride.

References:

Click here to expand or collapse this section

1. Stuzhin P.A., Ercolani C. Porphyrazines with Annulated Heterocycles, in The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Edrs). Academic Press: Amsterdam, 2003, Vol. 15, pp 263-364.
http://dx.doi.org/10.1016/b978-0-08-092389-5.50011-0

2. (a) Donzello M.P., Ou Z., Monacelli F., Ricciardi G., Rizzoli C., Ercolani C., Kadish K.M. Inorg. Chem. 2004, 43, 8626.
http://dx.doi.org/10.1021/ic048909w
(b) Donzello M.P., Ou Z., Dini D., Meneghetti M., Ercolani C., Kadish K.M. Inorg. Chem. 2004, 43, 8637.
http://dx.doi.org/10.1021/ic0489084
(c) Bergami C., Donzello M.P., Monacelli F., Ercolani C., Kadish K.M. Inorg. Chem. 2005, 44, 9862.
http://dx.doi.org/10.1021/ic051085d
(d) Donzello M.P., Viola E., Cai X., Mannina L., Rizzoli C., Ricciardi G., Ercolani C., Kadish K.M., Rosa A. Inorg. Chem. 2008, 47, 3903.
http://dx.doi.org/10.1021/ic702430j

3. Zimcik P., Novakova V., Miletin M., Kopecky K., Macroheterocycles, 2008, 1, 21-29.
http://dx.doi.org/10.6060/mhc2008.1.21

4. Gal'pern, M.G., Luk'yanets E.A. Zh. Obshch. Khim. 1969, 39, 2536–2541 (in Russ.)

5. Freyer W. Z. Chem. 1986, 26, 217–218.

6. Kudrevich S.V., van Lier J.E. Can. J. Chem. 1996, 74, 1718–1723.
http://dx.doi.org/10.1139/v96-189

7. Efimova S.V., Korzhenevskii A.B., Koifman O.I. Russ. J. Gen. Chem. 2008, 78, 1447–1451.
http://dx.doi.org/10.1134/S1070363208070293

8. (a) Gal'pern M.G.; Luk'yanets E.A. Zh. Obshch. Khim. 1971, 41, 2549–2552.
(b) Freyer W. J. Prakt. Chem./Chem.-Z. 1994, 336, 693–694.
http://dx.doi.org/10.1002/prac.19943360810

9. (a) Kudrevich S.V., Galpern M.G., Luk'yanets E.A. van Lier J.E. Can. J. Chem. 1996, 74, 508–515.
http://dx.doi.org/10.1139/v96-055
(b) Wen T.C., Chen S.P., Tsai C.Y. Synth. Met. 1998, 97, 105–112.
http://dx.doi.org/10.1016/S0379-6779(98)00115-5

10. Jaung J.-Y., Matsuoka M., Fukunishi K. J. Chem. Res., Synop. 1998, 284–285; (M) 1301–1323.
http://dx.doi.org/10.1039/a708049b

11. Jaung, J.-Y., Matsuoka M., Fukunishi K. Synthesis 1998, 1347–1351.
http://dx.doi.org/10.1055/s-1998-6092

12. Matsui N., Hatano H., Nagasaki F., Takahashi H. Japanese Patent 03232886, Oct. 16, 1991; Chem. Abstr. 1992, 117, 48624.

13. Gal'pern E.G., Luk'yanets E.A., Gal'pern M.G. Izv. Akad. Nauk SSSR Ser. Khim. 1973, 9, 1976–1980 (in Russ.)

Прикрепленный файл	Размер
MHC2010_t03n01_48-50.pdf	491.39 кб

Журнал "Макрогетероциклы"

Навигация

Languages

Новости

Поиск