Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Regioselective Synthesis of New Derivatives of 2-arylpyrido[3,4-b]pyrazines

Document Type : Research Article

Authors
Ahmad Poursattar Marjani
Jabbar Khalafy
Mohammad Taghi Kiani
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, I.R. IRAN
Abstract
A regioselective method for synthesis of pyrido[3,4-b]pyrazine derivatives were reported in high yield and short reaction times through condensation reaction between 3,4-diaminopyridine and arylglyoxals derivatives in DMF/EtOH at 55 oC. A regioselective method for synthesis of pyrido[3,4-b]pyrazine derivatives were reported in high yield and short reaction times through condensation reaction between 3,4-diaminopyridine and arylglyoxals derivatives in DMF/EtOH at 55 oC. A regioselective method for synthesis of pyrido[3,4-b]pyrazine derivatives were reported in high yield and short reaction times through condensation reaction between 3,4-diaminopyridine and arylglyoxals derivatives in DMF/EtOH at 55 oC. A regioselective method for synthesis of pyrido[3,4-b]pyrazine derivatives were reported in high yield and short reaction times through condensation reaction between 3,4-diaminopyridine and arylglyoxals derivatives in DMF/EtOH at 55 oC.
Keywords
Arylglyoxals
3
4-Diaminopyridine
Pyrido[3
4-b]pyrazines
Regioselective synthesis
Condensation reaction

Subjects

[1] Birkofer L., Das Verhalten Der Diazoketone Bei Der Katalytischen Hydrierung; Eine Neue Synthese Des Threonins. Chem. Ber., 80(1): 83-94 (1947).
[2] Dömling A., Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. Chem. Rev., 1069(1): 17-89 (2006).
[3] Yuan M.-C., Chiu M.-Y., Chiang C.-M., Wei K.-H., Synthesis and Characterization of Pyrido[3,4-b]pyrazine-Based Low-Bandgap Copolymers for Bulk Heterojunction Solar Cells. Macromolecules, 43(15): 6270–6277 (2010).
[4] Ying W., Yang J., Wielopolski M., Moehl T., Moser J.-E., Comte P.,  Hua J., Zakeeruddin S.M., Tiana  H., Grätzel M., New Pyrido[3,4-b]pyrazine-based Sensitizers for Efficient and Stable Dye-Sensitized Solar Cells. Chem. Sci., 5(1): 206-214 (2014).
[5] Zhang X., Mao J., Wang D., Li X., Yang J., Shen Z., Wu W., Li J., Ågren H., Hua J., Comparative Study on Pyrido[3,4-b]pyrazine-based Sensitizers by Tuning Bulky Donors for Dye-Sensitized Solar Cells. ACS Appl. Mater. Interfaces., 7(4): 2760-2771 (2015).
[6] Lee B.-L., Yamamoto T., Syntheses of New Alternating CT-Type Copolymers of Thiophene and Pyrido[3,4-b]pyrazine Units:  Their Optical and Electrochemical Properties in Comparison with Similar CT Copolymers of Thiophene with Pyridine and Quinoxaline. Macromolecules, 32(5): 1375-1382 (1999).
[7] Nikolou M., Dyer A.L., Steckler T.T., Donoghue E.P., Wu Z., Heston N.C., Rinzler A.G., Tanner D.B., Reynolds J.R., Dual N- and p-Type Dopable Electrochromic Devices Employing Transparent Carbon Nanotube Electrodes. Chem. Mater., 21(22): 5539-5547 (2009).
[8] Olczak A., Główka M.L., Gołka J., Szczesio M., Bojarska J., Kozłowska K., Foks H., Orlewska C., Is Planarity of Pyridin-2-yl- and Pyrazin-2-yl-formamide Thiosemicarbazones Related to Their Tuberculostatic Activity? X-Ray Structures of two Pyrazine-2-carboxamide-N′-carbonothioyl-hydrazones. J. Mol. Struct., 830(1): 171-175 (2007).
[9] Dubinina G.G., Platono M.O., Golovach S.M., Borysko P.O., Tolmachov A.O., Volovenko Y.M., Novel 5,7-Disubstituted 6-Amino-5H-pyrrolo[3,2-b]pyrazine-2,3-dicarbonitriles, the Promising Protein Kinase Inhibitors with Antiproliferative Activity. Eur. J. Med.Chem., 21(6): 727-737 (2006).
[10] Barbier P., Peyrot V., Sarrazin M., Rener G.A.S., Briand C., Differential Effects of Ethyl 5-Amino-2-methyl-1,2-dihydro-3-phenylpyrido[3,4-b]pyrazin-7-Yl Carbamate Analogs Modified at Position C2 on Tubulin Polymerization, Binding, and Conformational Changes. Biochemistry, 34(51): 16821-16829 (1995).
[11] Antoine M., Schuster T., Seipelt I., Aicher B., Teifel M., Günther E., Gerlach M., Marchand P., Efficient Synthesis of Novel Disubstituted Pyrido[3,4-b]pyrazines for the Design of Protein Kinase Inhibitors. Med. Chem. Commun., 7(2): 224-229 (2016).
[12] Jr Temple C., Laseter A.G., Rose J.D., Montgomery J.A., Synthesis of Potential Antimalarial Agents. VII. Azaquinolines. I. The Preparation of Some Pteridines and Pyrido[3,4‐b]pyrazines. J. Heterocycl. Chem., 7(5): 1195-1202 (1970).
[13] Kano S., Yuasa Y., Synthesis of 2‐Arylpyrido[3,4‐b]pyrazine Derivatives through Condensation of 3,4‐Diaminopyridine with β‐Keto Sulfoxides. J. Heterocycl. Chem., 20(3): 769-770 (1983).
[14] Herbich J., Kapturkiewicz A., Nowacki J., Goliński J., Dabrowski Z., Intramolecular Excited Charge-transfer States in Donor–acceptor Derivatives of Naphthalene and Azanaphthalenes. Phys. Chem. Chem. Phys., 3: 2438-2449 (2001).
[15] Mederski W.W.K.R., Kux D., Knoth M., Schwarzkopf-Hofmann M. J., Pyrido[3,4-b]pyrazines. A New Application of 2-Chloro-3,4-diaminopyridine. Heterocycles., 60(4): 925-932 (2003).
[16] Sako M., In Science of Synthesis:Houben-Weyl Methods of Molecular Transformations, Yamamoto Y., Stuttgart: Georg Thieme Verlag. 16: 1269-1290 (2004).
[17] Khalafy J., Parsa Habashi B., Poursattar Marjani A., Najafi Moghadam P., The Synthesis of 2-Arylquinoxaline Derivatives. Current Chem. Lett., 1(3): 139-146 (2012).
[18] Khalafy J., Poursattar Marjani A., Haghipour M., Regioselective Synthesis of 3-Arylpyrido [2,3-b]pyrazines by Reaction of Arylglyoxals with 2,3-Diaminopyridine. Current Chem. Lett., 2(1): 21-26 (2013).
[19] Poursattar Marjani A., Khalafy J., Chitan M., Mahmoodi S., Microwave-assisted Synthesis of Acridine-1,8(2H,5H)-diones via a One-pot, Three Component Reaction, Iran J. Chem. Chem. Eng. (IJCCE)., 36(2): 1-6 (2017).
[20] Poursattar Marjani A., Ebrahimi Saatluo B., Nouri F., An Efficient Synthesis of 4H-chromene Derivatives by a One-pot, Three-component Reaction, Iran J. Chem. Chem. Eng. (IJCCE)., 37(1): 149-157 (2018).
[21] Khalafy J., Eslamipour P., Poursattar Marjani A., Ahmadi Sabegh M., Synthesis of a New Series of 4H-benzo[H]chromenes by a Multicomponent Reaction under Solvent-free Microwave Conditions, Iran J. Chem. Chem. Eng. (IJCCE)., 38(4): 51-57 (2019).
[22] Riley H.A., Gray A.R. “Organic Syntheses”, John  Wiley & Sons. New York: Vol. II, 509 (1943).