[1]
Albini, A. Synthetic utility of amine N-oxides. Synthesis, 1993, 1993(3), 263-277.
[2]
Youssif, S. Recent trends in the chemistry of pyridine N-oxides. ARKIVOC, 2001, 12(4), 348-355.
[3]
Quagliano, J.V.; Fujita, J.; Franz, G.; Phillips, D.J.; Walmsley, J.A.; Tyree, S.Y. The Donor Properties of Pyridine N-Oxide. J. Am. Chem. Soc., 1961, 83(18), 3770-3773.
[4]
Carlin, R.L.; O’Connor, C.J.; Bhatia, S.N. Magnetic investigation of the electronic structure of hexakis (pyridine N-oxide) cobalt(II) perchlorate. J. Am. Chem. Soc., 1976, 98(3), 685-688.
[5]
Luh, T-Y. Trimethylamine N-oxide—A versatile reagent for organometallic chemistry. Coord. Chem. Rev., 1984, 60, 255-276.
[6]
Katritzky, A.R.; Lagowski, J.M. N-oxides and related compounds. Part XVIII. Proton nuclear magnetic resonance spectra of 4-substituted pyridines and pyridine 1-oxides. J. Chem. Soc., 1961, 43-46.
[7]
Garvey, R.G.; Nelson, J.H.; Ragsdale, R.O. The coordination chemistry of aromatic amine N-oxides. Coord. Chem. Rev., 1968, 3(3), 375-407.
[8]
Orchin, M.; Schmidt, P.J. Pyridine n-oxide complexes of platinum(II). Coord. Chem. Rev., 1968, 3(3), 345-373.
[9]
Kubota, T. Molecular Complexes and Their Spectra. XVIII. Iodine Complexes with Tertiary Amine N-Oxides. J. Am. Chem. Soc., 1965, 87(3), 458-468.
[10]
Ross, S.D.; Kelly, D.J.; Labes, M.M. Molecular compounds. VII. Interactions between 1,3,5-Trinitrobenzene and Pyridine-N-Oxides in Chloroform Solution. J. Am. Chem. Soc., 1956, 78(15), 3625-3627.
[11]
Chelucci, G.; Murineddu, G.; Pinna, G.A. Chiral pyridine N-oxides: useful ligands for asymmetric catalysis. Tetrahedron Asymmetry, 2004, 15(10), 1373-1389.
[12]
Kocovsky, P.; Malkov, A.V. From transition metals to organocatalysis. Russ. Chem. Bull., 2004, 53(9), 1806-1812.
[13]
Chen, J.; Takenaka, N. Helical chiral Pyridine N-Oxides: A new family of asymmetric catalysts. Chemistry Eur. J.,, 2009, 15(30), 7268-7276.
[14]
Jia, J.; Hubberstey, P.; Champness, N.R.; Schroder, M. Supramolecular chemistry of 4,4′-bipyridine-N,N′-dioxide in transition metal complexes: A rich diversity of coordinate, hydrogen-bond and aromatic stacking interactions. Struct. Bonding, 2009, 132, 135-161.
[15]
Kishbaugh, T.L.S. Six-membered ring systems: pyridine and benzo derivatives. Progress in Heterocyclic Chem., 2012, 24, 343-391.
[16]
Yeom, H-S.; Shin, S. Catalytic access to a-Oxo gold carbenes by N-O bond oxidants. Acc. Chem. Res., 2014, 47(3), 966-977.
[17]
Liu, X.; Lin, L.; Feng, X.; Chiral, N. N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis. Org. Chem. Front., 2014, 1, 298-302.
[18]
Liu, N.; Shu, Y-J.; Wang, B-Z.; Li, X-Z.; Bi, F-Q. Cyclization: A useful approach for the synthesis of nitrogen heterocyclic N-oxides. Curr. Org. Chem., 2015, 19(19), 1896-1915.
[19]
Koukal, P. Ulč. J.; Nečas, D.; Kotora, M. Pyridine N-Oxides and derivatives thereof in organocatalysis; Heterocyclic N-Oxides, 2017, pp. 29-58.
[20]
Katritzky, A.R. The chemistry of the aromatic heterocyclic N-oxides. Q. Rev. Chem. Soc., 1956, 10, 395-406.
[21]
Abramovitch, R.A.; Grins, G.; Rogers, R.B.; Shinkai, I. Alkylation of pyridine 1-oxides and related compounds with activated acetylenes. A novel molecular rearrangement of heteroaromatic N-oxides. J. Am. Chem. Soc., 1976, 98(18), 5671-5677.
[22]
Vozza, J.F. Reactions of 2-Picoline 1-Oxide with Reactive Halides. J. Org. Chem., 1962, 27(11), 3856-3860.
[23]
Karayannis, N.M. Metal complexes of aromatic amine n-oxides. Coord. Chem. Rev., 1973, 11(2), 93-159.
[24]
Garvey, R.G.; Ragsdale, R.O. Co-ordination complexes of oxovanadium (IV) with substituted pyridine 1-oxides. Coord. Chem. Rev., 1967, 29(3), 745-754.
[25]
Lever, A.B.P.; Lewis, J.; Nyholm, R.S. Metal complexes of picolinic acid N-oxide. J. Chem. Soc., 1962, 5262-5270.
[26]
Simpson, P.G.; Vinciguerra, A.; Guagliano, J.V. The Donor Properties of 2,2′-Bipyridine N,N′-Dioxide. Inorg. Chem., 1963, 2(2), 282-286.
[27]
Sartorelli, U.; Canziani, F.; Zingales, F. Substituted halocarbonyl complexes of Rhenium(I) with ligands having oxygen as the donor atom. Inorg. Chem., 1966, 5(12), 2233-2236.
[28]
Reiff, W.M.; Baker, A. Transition metal complexes of 2,2′,2”-terpyridine 1,1′,1”-trioxide. Inorg. Chem., 1970, 9(3), 570-576.
[29]
Mirrison, M.M.; Sawyer, D.T. 2,2′-Bipyridine 1,1′-dioxide and 2,2′,2”-terpyridine 1,1′,1”-trioxide complexes of manganese(II), -(III), and -(IV). Inorg. Chem., 1978, 17(2), 338-339.
[30]
Thummel, R.P.; Lefoulon, F. Polyaza cavity shaped molecules. 2. Annelated derivatives of 2,2′-biquinoline and the corresponding N-oxides. J. Org. Chem., 1985, 50(5), 666-670.
[31]
Ito, K.; Nagata, T.; Tanaka, K. Synthesis and electrochemical properties of transition metal complexes of 2,2′:6′,2”-terpyridine 1,1”-dioxide. Inorg. Chem., 2001, 40(24), 6331-6333.
[32]
Amoroso, A.J.; Burrows, M.W.; Dickinson, A.A.; Jones, C.; Willock, D.J.; Wong, W-T. Geometrical preferences of complexes of terpyridine N-oxide ligands: synthesis and crystal structures of nickel(II) with terpyridine 1,1′,1″-trioxide, terpyridine 1,1″-dioxide and terpyridine 1-oxide. J. Chem. Soc., Dalton Trans., 2001, 0, 225-227.
[33]
Fallahpour, R.A.; Neuburger, M. An efficient, easy route for the synthesis of 2,2′:6′,2′′‐terpyridine 1′‐oxides. Eur. J. Org. Chem., 2001, 1853-1856.
[34]
Musumeci, A.; Bonomo, R.P.; Cucinotta, V.; Seminara, A. Lanthanide complexes with n-oxides. Complexes with pyridine 1-oxide, 2,2′-bipyridine 1,1′-dioxide and 2,2′,2″-terpyridine 1,1′, 1″-trioxide. Inorg. Chim. Acta, 1982, 59, 133-140.
[35]
Collado, D.; Perez-Inestrosa, E.; Suau, R.; Desvergne, J.P.; Bouas-Laurent, H. Bis(isoquinoline N-oxide) pincers as a new type of metal cation dual channel fluorosensor. Org. Lett., 2002, 4(5), 855-858.
[36]
Dyker, G.; Holzer, B.; Henkel, G. A chiral bis-N-oxide isoelectronic with Jacobsen’s salen ligand. Tetrahedron Asymmetry, 1999, 10(17), 3297-3307.
[37]
Cerecetto, H.; Gerpe, A. ’ Gonzalez, M.; Aran, V.J.; de Ocariz, C.O. Pharmacological Properties of Indazole Derivatives: Recent Developments. Mini Rev. Med. Chem., 2005, 5(10), 869-878.
[38]
Mfuh, A.M.; Larionov, O.V. Heterocyclic N-Oxides – An emerging class of therapeutic agents. Curr. Med. Chem., 2015, 22(24), 2819-2857.
[39]
Dos Santos Fernandes, G.F.; Pavan, A.R.; Dos Santos, J.L. Heterocyclic N-oxides – A promising class of agents against tuberculosis, malaria and neglected tropical diseases. Curr. Pharm. Des., 2018, 24(12), 1325-1340.
[40]
Boyle, R.G.; Travers, S. N-oxide-containing pharmaceutical compounds.
PCT patent, WO2008139152A1, November 20, 2008.
[41]
Mlostoń, G.; Romański, J.; Jasiński, M.; Heimgartner, H. Exploration of 4,5-dimethyl-1H-imidazole N-oxide derivatives in the synthesis of new achiral and chiral ionic liquids. Tetrahedron Asymmetry, 2009, 20(9), 1073-1080.
[42]
Pieczonka, A.M.; Mlostoń, G.; Heimgartner, H. Synthesis of bis-heterocyclic 1h‐imidazole 3‐oxides from 3‐oxido‐1h‐imidazole‐4‐carbohydrazides. Helv. Chim. Acta, 2012, 95(3), 404-414.
[43]
Mlostoń, G.; Mucha, P.; Heimgartner, H. Chiral Imidazoles and imidazole N-Oxides as ligands for stereoselective cyclopropanation reactions. Lett. Org. Chem., 2012, 9(2), 89-91.
[44]
Kwiatkowski, P.; Muchac, P.; Mlostoń, G.; Jurczak, J. Novel chiral C 2-Symmetric bisimidazole-n-oxides as promising organocatalysts for enantioselective allylation of aromatic aldehydes. Synlett, 2009, 11, 1757-1760.
[45]
Mloston, G.; Wroblewska, A.; Obijalska, E.; Heimgartner, H. Optically active imidazole N-oxides derived from L-prolinamine. Tetrahedron Asymmetry, 2013, 24(15-16), 958-965.
[46]
Mloston, G.; Urbaniak, K.; Wojciechowska, A.; Linden, A.; Heimgartner, H. Unexpected course of the reaction of 2-unsubstituted 1h-imidazole 3-oxides with ethyl acrylate. Helv. Chim. Acta, 2012, 95(4), 577-585.
[47]
Wroblewska, A.; Mloston, G.; Heimgartner, H. Synthesis of optically active polycyclic N-heterocycles derived from L-prolinamine. Tetrahedron Asymmetry, 2015, 26(8-9), 505-509.
[48]
Adiulin, E.I.; Kutasevich, A.V.; Mityanov, V.S.; Tkach, I.I.; Koldaeva, T.Y. Nucleophilic halogenation of imidazole N-oxides. Chem. Heterocycl. Compd., 2015, 51(5), 500-502.
[49]
Mloston, G.; Wroblewska, A.; Heimgartner, H. Synthesis of optically active trifluoromethyl-substituted 2,3-dihydroimidazo[2,1-b]oxazoles. J. Fluor. Chem., 2016, 189, 1-6.
[50]
Mityanov, V.S.; Kutasevich, A.V.; Krayushkin, M.M.; Lichitsky, B.V.; Dudinov, A.A.; Komogortsev, A.N.; Kuzmina, L.G. Condensation of imidazole N-oxide with Meldrum’s acid and aldehydes: a new method for C2-functionalization of 2-unsubstituted imidazole N-oxides. Tetrahedron Lett., 2016, 57(48), 5315-5316.
[51]
Hossain, M.; Pradhan, K.; Nanda, A.K. An expeditious synthetic protocol for chlorination of imidazole N-oxide: Synthesis of 2-chloroimidazoles. Tetrahedron Lett., 2017, 58(39), 3772-3776.
[52]
Ten, Y.A.; Salnikov, O.G.; Amitina, S.A.; Stass, D.V.; Rybalova, T.V.; Kazantsev, M.S. Bogomyakov, Artem S.; Mostovich, Evgeny A.; Mazhukin, Dmitrii G. The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4H-imidazole N-oxide series. RSC Advances, 2018, 8, 26099-26107.
[53]
Aguirre, G.; Boiani, M.; Cerecetto, H.; Gerpe, A.; Gonzalez, M.; Sainz, Y.F.; Denicola, A.; De Ocariz, C.O.; Nogal, J.J.; Montero, D. Novel antiprotozoal products: imidazole and benzimidazole N-oxide derivatives and related compounds. Arch. Pharm., 2004, 337(5), 259-270.
[54]
Nyerges, M.; Viranyi, A.; Zhang, W.; Groundwater, P.W.; Blasko, G.; Toke, L. Synthesis of indazole-N-oxides via the 1,7-electrocyclization of azomethine ylides. Tetrahedron, 2004, 60(44), 9937-9944.
[55]
Gerpe, A.; Piro, O.E.; Cerecetto, H.; Gonzalez, M. Structure of indazole N1-oxide derivatives studied by X-ray, theoretical methods, 1H, 13C, 15N NMR and EI/MS. J. Mol. Struct., 2007, 871(1-3), 98-107.
[56]
Gerpe, A.; Aguirre, G.; Boiani, L.; Cerecetto, H.; González, M.; Olea-Azar, C.; Rigol, C.; Maya, J.D.; Morello, A.; Piro, O.E.; Arán, V.J.; Azqueta, A.; de Ceráin, A.L.; Monge, A.; Rojas, M.A.; Yaluff, G. Indazole N-oxide derivatives as antiprotozoal agents: synthesis, biological evaluation and mechanism of action studies. Bioorg. Med. Chem., 2006, 14(10), 3467-3480.
[57]
Qu, S-J.; Liu, Q-W.; Tan, C-H.; Jiang, S-H.; Zhu, D-Y. New indole N-oxide alkaloids from Evodia fargesii. Planta Med., 2006, 72(3), 264-266.
[58]
Kaji, E.; Zen, S. Boron trifluoride-promoted transformation of 3,5-bis(methoxycarbonyl)-4-phenylisoxazoline N-oxide into 3H-indole N-oxide derivative. Heterocycles, 1979, 13(1), 187-190.
[59]
Canestrari, S.; Mar'in, A.; Sgarabotto, P.; Righi, L.; Greci, L. New insights
on the reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3Hindole
N-oxide: an indolic nitrone. Crystal structures of 1-diethylphosphoryl-
2-phenyl-3-phenylamino-1H-indole and 2-phenyl-4-phenylimino-4H-3,1-
benzoxazine. J. Chem. Soc. Perkin 2,, 2000, 4, 833-838.
[60]
Greci, L.; Tommasi, G. Bruni, Paolo; Sgarabotto, P.; Righi, L. Diastereoselectivity in 1,3-dipolar cycloaddition reactions between indolic nitrones and electron-deficient alkenes. Eur. J. Org. Chem., 2001, 16, 3147-3153.
[61]
Lantsetti, N.A.; Ryabova, S.Y.; Alekseeva, L.M.; Shashkov, A.S.; Granik, V.G. Synthesis and properties of [1,4]diazepino[6,5-b]indoles. Russ. Chem. Bull., 2002, 51(3), 506-512.
[62]
Yamada, F.; Kawanishi, A.; Tomita, A.; Somei, M. The chemistry of indoles. 121. The first preparation of the unstable 1-hydroxy-2,3-dimethylindole, and structural determination of its air-oxidized product, 3-hydroxy-2,3-dimethyl-3H-indole N-oxide. ARKIVOC, 2003, (8), 102-111.
[63]
Roh, H.J.; Kim, G.; Cho, S.; Ryu, J.Y.; Lee, J.; Kim, J.N. Synthesis of isatin-conjugated 3H-indole-N-oxides and their serendipitous conversion to spiroindolenines. Tetrahedron Lett., 2018, 59(15), 1484-1488.
[64]
Pan, W.; Dong, D.; Sun, S.; Liu, Q. One-pot synthesis of substituted indole N-oxides: TiCl4-mediated Baylis-Hillman reaction of a-oxo cyclic ketene-S,S-acetal with ortho-nitrobenzaldehydes and subsequent intramolecular cyclization. Synlett, 2006, (7), 1090-1094.
[65]
Yang, Y.; Wang, X.; Li, Y.; Zhou, B.A. [4+1] Cyclative Capture Approach to 3H-Indole-N-oxides at Room Temperature by Rhodium(III)-Catalyzed C-H Activation. Angew. Chem. Int. Ed., 2015, 54(51), 15400-15404.
[66]
Hulme, C.; Mathew, R.; Moriarty, K.; Miller, B.; Ramanjulu, M.; Cox, P.; Souness, J.; Page, K.M.; Uhl, J.; Travis, J.; Labaudiniere, R.; Huang, F.; Djuric, S.W. Orally active indole N-oxide PDE4 inhibitors. Bioorg. Med. Chem. Lett., 1998, 8(21), 3053-3058.
[67]
Sugie, Y.; Hirai, H.; Inagaki, T.; Ishiguro, M.; Kim, Y.J.; Kojima, Y.; Sakakibara, T.; Sakemi, S.; Sugiura, A.; Suzuki, Y.; Brennan, L.; Duignan, J.; Huang, L.H.; Sutcliffe, J.; Kojima, N. A new antibiotic CJ-17665 from Aspergillus ochraceus. J. Antibiot. , 2001, 54(11), 911-916.
[68]
Igeta, H.; Tsuchiya, T.; Yamada, M.; Arai, H. Synthesis of pyridazine derivatives. IX. Photo-induced oxygenation of hydrocarbons by pyridazine N-oxide. Chem. Pharm. Bull., 1968, 16(4), 767-769.
[69]
Tsuchiya, T.; Arai, H.; Igeta, H. Photo-induced oxygenation by pyridazine N-oxide. II. Formation of epoxides from ethylenic compounds. Tetrahedron Lett., 1969, (32), 2747-2750.
[70]
Tang, Y.; He, C.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Energetic 1,2,5-Oxadiazolo-Pyridazine and its N-Oxide. Chemistry Eur. J.,, 2017, 23(60), 15022-15025.
[71]
Altuntas, T.G.; Gorrod, J.W. The in vitro oxidation of isomeric aromatic diazines to mono-N-oxides. Pharm. Sci. Commun, 1994, 4(2), 117-124.
[72]
Igeta, H.; Tsuchiya, T.; Nakai, T. Reactions of pyridazine N-oxides with organometallic compounds. Tetrahedron Lett., 1969, (31), 2667-2670.
[73]
Kurita, J.; Kakusawa, N.; Yasuike, S.; Tsuchiya, T. Reaction of pyridazine N-oxides with pyridynes: formation of the first examples of pyrido-oxepins. Heterocycles, 1990, 31(11), 1937-1940.
[74]
Lian, Y.; Coffey, S.B.; Li, Q.; Londregan, A.T. Preparation of Heteroaryl Ethers from Azine N-Oxides and Alcohols. Org. Lett., 2016, 18(6), 1362-1365.
[75]
Roudesly, F.; Veiros, L.F.; Oble, J.; Poli, G. Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N-Oxides. Org. Lett., 2018, 20(8), 2346-2350.
[76]
Leclerc, J-P.; Fagnou, K. Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides. Angew. Chem. Int. Ed., 2006, 45(46), 7781-7786.
[77]
Popp, C.J.; Garlough, G.D. Transition metal complexes of diazine N-oxides. J. Inorg. Nucl. Chem., 1981, 43(3), 501-507.
[78]
Kurita, J.; Kakusawa, N.; Yasuike, S.; Tsuchiya, T. Reaction of Pyridazine N-Oxides with Pyridynes: Formation of the First Examples of Pyrido-oxepins. Heterocycles, 1990, 31(11), 1937-1940.
[79]
Giorgio, B.; Cesare, C.; Gabriele, N.; Francesco, S. 17-(Pyridazine-N-oxide)-
substituted steroidal compounds active on the cardiovascular system. European
Patent EP0551953A2, January 16, 1992.
[80]
Ikekawa, N.; Honna, Y. Photochemical reactions of pyrazine N-oxides. Tetrahedron Lett., 1967, (13), 1197-1200.
[81]
Paudler, W.W.; Humphrey, S.A. Basicities and H-D exchange of pyrazine N-oxide. J. Org. Chem., 1970, 35(10), 3467-3470.
[82]
Uchimaree, F.; Okada, S.; Kosasayama, A.; Konno, T. Mass spectra of pyrazine N-oxide. Pyrazine derivatives. III. J. Heterocycl. Chem., 1971, 8(1), 99-104.
[83]
Okada, S.; Kosasayama, A.; Konno, T.; Uchimaru, F. Pyrazine derivatives. II. Synthesis, reactions, and spectra of pyrazine N-oxide derivatives. Chem. Pharm. Bull. , 1971, 19(7), 1344-1357.
[84]
Stanovnik, B.; Tišler, M.R.; Katritxky, A.; Denisko, O.V. The tautomerism of heterocycles. six-membered heterocycles: Part 1, annular tautomerism. Adv. Heterocycl. Chem., 2001, (81), 253-303.
[85]
Andersson, H.; Banchelin, T.S-L.; Das, S.; Gustafsson, M.; Olsson, R.; Almqvist, F. Complete regioselective addition of grignard reagents to pyrazine n-oxides, toward an efficient enantioselective synthesis of substituted piperazines. Org. Lett., 2010, 12(2), 284-286.
[86]
Aitken, R.A.; Fodi, B.; Palmer, M.H.; Slawin, A.M.Z.; Yang, J. Experimental and theoretical molecular and electronic structures of the N-oxides of pyridazine, pyrimidine and pyrazine. Tetrahedron, 2012, 68(29), 5845-5851.
[87]
Speca, A.N.; Karayannis, N.M.; Pytlewski, L.L.; Owens, C. Cobalt(II), nickel(II), and copper(II) nitrate complexes with pyrazine N-oxide. J. Inorg. Nucl. Chem., 1976, 38(1), 91-94.
[88]
Speca, A.N.; Karayannis, N.M.; Pytlewski, L.L. Transition metal perchlorate complexes with pyrazine N-oxide. J. Inorg. Nucl. Chem., 1973, 35(9), 3113-3128.
[89]
Vicentini, G.; Zinner, L.B. Pyrazine N-oxide adducts of some lanthanide perchlorates. Inorg. Nucl. Chem. Lett., 1974, 10(8), 629-635.
[90]
Alencar, F.L.; Matos, J.R.; Zinner, L.B. Pyrazine-N-oxide (pyzNO) complexes of lanthanide(III) trifluoroacetates (TFA). J. Alloys Compd., 1994, 207-208, 461-464.
[91]
Marinho, E.P.; Araujo Melo, D.M.; Zinner, L.B.; Vicentini, G.; Zukerman-Schpector, J.; Zinner, K. Hydrated neodymium(III) and europium(III) picrate complexes with pyrazine-N-oxide. J. Alloys Compd., 2000, 303-304, 116-1120.
[92]
Usui, I.; Lin, D.W.; Masuda, T.; Baran, P.S. Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε. Org. Lett., 2013, 15(9), 2080-2083.
[93]
Tone, H.; Matoba, K.; Goto, F.; Torisawa, Y.; Nishi, T.; Minamikawa, J-I. Progress in the synthesis of opc-15161: easy access to dioxygenated pyrazine n-oxide structure. Org. Process Res. Dev., 2000, 4(5), 312-317.
[94]
Xia, Q.; Zhang, L.; Zhang, J.; Sheng, R.; Yang, B.; He, Q.; Hu, Y. Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4-benzotriazine 1,4-dioxide derivatives. Eur. J. Med. Chem., 2011, 46(3), 919-926.
[95]
Chowdhury, G.; Sarkar, U.; Pullen, S.; Wilson, W.R.; Rajapakse, A.; Fuchs-Knotts, T.; Gates, K.S. DNA strand cleavage by the phenazine di-N-oxide natural product myxin under both aerobic and anaerobic conditions. Chem. Res. Toxicol., 2012, 25(1), 197-206.
[96]
Cugola, A.; Donati, D.; Guarneri, M.; Micheli, F.; Missio, A.; Pecunioso, A.; Reggiani, A.; Tarzia, G.; Zanirato, V. Synthesis and biological evaluation of pyrido[2,3-b]pyrazine and pyrido[2,3-b]pyrazine-N-oxide as selective glycine antagonists. Bioorg. Med. Chem. Lett., 1996, 6(22), 2749-2754.
[97]
Rusinov, V.L.; Kovalev, I.S.; Kozhevnikov, D.N.; Ustinova, M.M.; Chupakhin, O.N.; Pokrovskii, A.G.; Ilicheva, T.N.; Belanov, E.F.; Bormotov, N.I.; Serova, O.A.; Volkov, G.N. Synthesis and antiviral activity of 2-amino-3-ethoxycarbonylpyrazine derivatives. Pharm. Chem. J., 2005, 39(12), 630-635.
[98]
Cresswell, R.M.; Maurer, H.K.; Strauss, T.; Brown, G.B. Purine N-Oxides. XIV. A Total synthesis of a Pyrimidine N-Oxide, a Pteridine 1-N-Oxide, and Xanthine 3-N-Oxide. J. Org. Chem., 1965, 30(2), 408-410.
[99]
Delia, T.J.; Venton, D.L. Pyrimidine N-oxide. Preparation of 6-chloro-2,4-diaminopyrimidine 3-N-oxide and its reactions. J. Heterocycl. Chem., 1972, 9(1), 73-75.
[100]
Muller, J.C.; Ramuz, H.; Wagner, H.P. A new route to the synthesis of 2-amino-6-(methoxycarbonyl)amino-4-(tetrahydropyridyl)pyrimidine 1-oxide. Helv. Chim. Acta, 1983, 66(3), 809-813.
[101]
Yamanaka, H.; Sakamoto, T.; Niitsuma, S. Pyrimidine N-oxides: syntheses, structures, and chemical properties. Heterocycles, 1990, 31(5), 923-967.
[102]
Ranjbar, M.; Celik, O.; Mahmoudi, N.; Heydar, S.; Sheshmani, S.; Mobarakeh, N.A. Synthesis of lead(ii) minoxidil coordination polymer: A new precursor for lead(ii) oxide and lead(ii) hydroxyl bromide. J. Inorg. Organomet. Polym., 2012, 22(4), 837-844.
[103]
Hirshey, S.J.; Falany, C.N. Purification and characterization of rat liver minoxidil sulphotransferase. Biochem. J., 1990, 270(3), 721-728.
[104]
Youssif, S. Recent trends in the chemistry of pyridine N-oxides. ARKIVOC, 2001, (1), 242-268.
[105]
Zhang, L.; Cole, J.M. Anchoring groups for dye-sensitized solar cells. ACS Appl. Mater. Interfaces, 2015, 7(6), 3427-3455.
[106]
Liu, Y.; Liu, D.; Wang, C. Bivalent metal-based MIL-53 analogues: Synthesis, properties and application. J. Solid State Chem., 2015, 223, 84-94.
[107]
Shiina, I. An adventurous synthetic journey with MNBA from its reaction chemistry to the total synthesis of natural products. Bull. Chem. Soc. Jpn., 2014, 87(2), 196-233.
[108]
Odani, R.; Hirano, K.; Satoh, T.; Miura, M. Copper-mediated formally dehydrative biaryl coupling of azine N-Oxides and oxazoles. J. Org. Chem., 2015, 80(4), 2384-2391.
[109]
Chen, Y. g; Huang, J.; Hwang, T.-L.; Chen, M.J.; Tedrow, J.S.; Farrell, R.P.; Bio, M.M.; Cui, S. Highly regioselective halogenation of pyridine N-oxide: Practical access to 2-halo-substituted pyridines. Org. Lett., 2015, 17(12), 2948-2951.
[110]
Cenacchi, V.; Battaglia, R.; Cinato, F.; Riccardi, B.; Spinabelli, D.; Brogin, G.; Puccini, P.; Pezzetta, D. In vitro and in vivo metabolism of CHF 6001, a selective phosphodiesterase (PDE4) inhibitor. Xenobiotica, 2015, 45(8), 693-710.
[111]
Ishihara, K.; Lu, Y. Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and. Chem. Sci., 2016, 7(2), 1276-1280.
[112]
Brugarolas, P.; Freifelder, R.; Cheng, S-H.; DeJesus, O. Synthesis of meta-substituted [18F]3-fluoro-4-aminopyridine via direct radiofluorination of pyridine N-oxides. Chem. Commun. , 2016, 52(44), 7150-7152.
[113]
Saikia, B.; Khatioda, R.; Bora, P.; Sarma, B. Pyridine N-oxides as coformers in the development of drug cocrystals. CrystEngComm, 2016, 18(43), 8454-8464.
[114]
Kaieda, A.; Takahashi, M.; Takai, T.; Goto, M.; Miyazaki, T.; Hori, Y.; Unno, S.; Kawamoto, T.; Tanaka, T.; Itono, S.; Takagi, T.; Hamada, T.; Shirasaki, M.; Okada, K.; Snell, G.; Bragstad, K.; Sang, B.C.; Uchikawa, O.; Miwatashi, S. Structure-based design, synthesis, and biological evaluation of imidazo[1,2-b]pyridazine-based p38 MAP kinase inhibitors. Bioorg. Med. Chem., 2018, 26(3), 647-660.
[115]
Balzarini, J.; Stevens, M.; De Clercq, E.; Schols, D.; Pannecouque, C. Pyridine N-oxide derivatives: unusual anti-HIV compounds with multiple mechanisms of antiviral action. J. Antimicrob. Chemother., 2005, 55, 135-138.
[116]
Fallahpour, R-A.; Neuburger, M. An efficient, easy route for the synthesis of 2,2′:6′,2”-terpyridine 1′-oxides. Eur. J. Org. Chem., 2001, 10, 1853-1856.
[117]
Amoroso, A.J.; Burrows, M.W.; Haigh, R.; Hatcher, M.; Jones, M.; Kynast, U.; Malik, K.M.; Sendor, D. The synthesis and characterisation of europium terpyridine-N-oxide complexes. Dalton Trans., 2007, 16, 1630-1638.
[118]
Amoroso, A.J.; Burrows, M.W.; Coles, S.J.; Haigh, R.; Farley, R.D.; Hursthouse, M.B.; Jones, M.; Malik, K.M.; Murphy, D.M. The synthesis and structure of terpyridine-N-oxide complexes of copper(II) perchlorate. Dalton Trans., 2008, 0, 506-513.
[119]
Amoroso, A.J.; Burrows, M.W.; Dickinson, A.A.; Jones, C.; Willock, D.J.; Wong, W-T. Geometrical preferences of complexes of terpyridine N-oxide ligands: synthesis and crystal structures of nickel(II) with terpyridine 1,1′,1”-trioxide, terpyridine 1,1”-dioxide and terpyridine 1-oxide. Dalton Trans., 2001, 0, 225-227.
[120]
Lopez, J.P.; Kraus, W.; Reck, G.; Thuenemann, A.; Kurth, D.G. Synthesis, structure and reactivity of the homoleptic iron(II) complex of the novel 4′-(4”'-pyridyl-N-oxide)-2,2′:6′,2”-terpyridine ligand. Inorg. Chim. Acta, 2005, 358(12), 3384-3390.
[121]
Hamaguchi, T.; Inoue, Y.; Ujimoto, K.; Ando, I. Synthesis, crystal structure and electrochemistry of a ruthenium complex coordinated with an ambidentate 2-mercaptopyridinato N-oxide ligand. Polyhedron, 2008, 27(9-10), 2031-2034.
[122]
Wong, W-L.; Lee, W-S.; Kwong, H-L. Synthesis of new chiral terpyridine mono-N-oxide and di-N-oxide ligands and their applications in coppercatalyzed asymmetric cyclopropanation. Tetrahedron Asymmetry, 2002, 13(14), 1485-1492.
[123]
Wong, W-L.; Lee, C-S.; Leung, H-K.; Kwong, H-L. The first series of chiral 2,2′:6′,2”-terpyridine tri-N-oxide ligands for Lewis base-catalyzed asymmetric allylation of aldehydes. Org. Biomol. Chem., 2004, 2, 1967-1969.