ASSESSMENTS OF ELECTRONIC PROPERTIES IN PHENOTHIAZINE CARBALDEHYDE REGIOISOMERS SERIES

Balász  BRÉM; Emese  GÁL; Tamás  LOVÁSZ; Castelia  CRISTEA; Luiza  GĂINĂ; Luminiţa  SILAGHI-DUMITRESCU

ASSESSMENTS OF ELECTRONIC PROPERTIES IN PHENOTHIAZINE CARBALDEHYDE REGIOISOMERS SERIES

Authors

Balász BRÉM Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: bbrem@chem.ubbcluj.ro. https://orcid.org/0000-0001-6091-5817
Emese GÁL Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: emese.gal@ubbcluj.ro. https://orcid.org/0000-0003-4324-0787
Tamás LOVÁSZ Department of Chemisty and Chemical Engineering in Hungarian Language, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: tlovasz@chem.ubbcluj.ro. https://orcid.org/0000-0003-2923-7442
Castelia CRISTEA Faculty of Chemistry and Chemical Engineering, “Babeș-Bolyai” University, Cluj-Napoca, Romania. Email: castelia.cristea@ubbcluj.ro. https://orcid.org/0000-0003-1138-2596
Luiza GĂINĂ Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: gluiza@chem.ubbcluj.ro. https://orcid.org/0000-0002-1328-0107
Luminiţa SILAGHI-DUMITRESCU Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: lusi@chem.ubbcluj.ro. https://orcid.org/0000-0001-8800-4839

Keywords:

Phenothiazine carbaldehyde, UV-Vis absorption, Fluorescence, DFT

Abstract

Regioselective C-formylation of phenothiazine using N,N-dimethylformamide is revisited and optimized synthesis of 10-methyl-10Hphenothiazine-carbaldehyde regioisomers are presented. Recorded NMR and UV-Vis spectroscopic data are compared in the regioisomers series. Fluorescence emissions in the visible range are described. Density Functional Theory (DFT) computational results regarding structural characteristics in the regioisomers series are supporting the recorded spectral properties.

References

K. Pluta, B. Morak-Młodawska, M Jeleń, Eur. J. Med. Chem., 2011, 46, 3179.

a) C. Garcia, R. Oyola, L.E. Pinero, R. Arce, J. Silva, V. Sanchez, J. Phys. Chem. A. 2005, 109, 3360; b) Meyer T., Ogermann D., Pankrath A., Kleinermanns K., Müller T.J.J., J. Org. Chem. 2012, 77, 3704; c) Zhang X., Qiu X., Lu R., Zhou H., Xue P., Liu X., Talanta, 2010, 82,1943.

A. Vilsmeier, A. Haak, Ber. Dtsch. Chem. Ges., 1927, 60(1), 119.

J.C. Duff, J. Chem. Soc., 1941, 547.

Ng.Ph. Buu-Hoï, N.G. Hoán, J. Chem. Soc., 1951, 1834.

V. Fărcăşan, I. Oprean, C. Bodea, Rev. Roum. Chim., 1968, 13, 647; (b) V. Fărcăşan, I. Oprean, C. Bodea, Rev. Roum. Chim., 1970, 15, 1433.

Y. Tian, M. Zhang, X. Yu, G. Xu, Y. Ren, J. Yang, J. Wu, X. Zhang, X. Tao, S. Zhang, M. Jiang, Chem. Phys. Lett., 2004, 388, 325.

L. Gaina, D. Porumb, I. Silaghi-Dumitrescu, C. Cristea, L. Silaghi-Dumitrescu, Can. J. Chem., 2010, 88(1), 42.

a) G. Gauquil, A. Cassadavall, E. Cassadavall, Bull. Soc. Chim. Fr., 1960, 1049; b) H.W. Gschwend, H.R. Rodriguez, Org. React., 1979, 26, 47; c) A. Halberg, A.R. Martin, J. Heterocycl. Chem., 1982, 19, 433; d) A. Halberg, A.R. Martin, Synth. Commun., 1983, 13, 467; e) A. Halberg, I. Al-Showaier, A.R. Martin, J. Heterocycl. Chem., 1983, 20, 1435.

J. Mortier, T.H. Nguyen, D. Tilly, A.S. Castanet, ARKIVOC, 2007, vi, 47.

A.R. Katritzky, L.M. Vazquez de Miguel, G.W. Rewcastle, Synthesis, 1988, 3, 215.

A. Hallberg, A. Martin, J. Heterocyclic Chem., 1982, 19, 433.

a) H. Gilman, P.R. Van Ess, D.A. Shirley, J. Am. Chem. Soc., 1944, 66, 1214; b) R.D. Nelson, Iowa State Coll. J. Sci., 1953, 27, 229.

S. Ebdrup, J. Chem. Soc., Perkin Trans., 1998, 1, 1147.

SPARTAN 06 Wavefunction, Inc. Irvine, CA.

L. Yang, J.K. Feng, A.M. Ren, J. Org. Chem., 2005, 70, 5987.

G. Cerbai, L.Turbanti, Bollettino chimico farmaceutico, 1969, 108 (7), 433.

G. Cauquil, A. Casadevall, Bull. Soc. Chim.Fr., 1955, 768.

H. Spreitzer, M. Scholz, G. Gescheidt, J. Daub, Liebigs Annales, 1996, 12, 2069.

J. Bergman, L. Renstrom, B. Sjoberg, Tetrahedron, 1980, 36 (17), 2505.

STUDIA UBB CHEMIA, Volume 60 (LX), No. 2, June 2015

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Published

2015-06-30

How to Cite

BRÉM, B. ., GÁL, E. ., LOVÁSZ, T. ., CRISTEA, C. ., GĂINĂ, L. ., & SILAGHI-DUMITRESCU, L. . (2015). ASSESSMENTS OF ELECTRONIC PROPERTIES IN PHENOTHIAZINE CARBALDEHYDE REGIOISOMERS SERIES. Studia Universitatis Babeș-Bolyai Chemia, 60(2), 271–279. Retrieved from https://studia.reviste.ubbcluj.ro/index.php/chemia/article/view/8449