[1]
Sindhu, T.J.; Arikkatt, S.D.; Vincent, G.; Chandran, M.; Bhat, A.R.; Krishnakumar, K. Biological activities of oxazine and its derivatives: A review. Int. J. Pharm. Sci. Res., 2013, 4, 134-143.
[2]
Tietze, L.F. Domino reactions in organic synthesis. Chem. Rev., 1996, 96, 115-136.
[3]
Tsoungas, P.G. Synthesis of 1,2-oxazines and their N-oxides. Heterocycles, 2002, 57, 1149-1178.
[4]
Varela, J.A.; Saa, C. Metal-catalyzed cyclizations to pyran and oxazine derivatives. Synthesis, 2016, 48(20), 3470-3478.
[5]
Smist, M.; Kwiecien, H. Synthesis of 3,4-dihydro-2H-1,4-benzoxazines and their oxo derivatives: A review. Curr. Org. Synth., 2014, 11, 676-695.
[6]
Achari, B.; Mandal, S.B.; Dutta, P.K.; Chowdhury, C. Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives. Synlett, 2004, 14, 2449-2467.
[7]
Pfrengle, F.; Reissig, H.U. Amino sugars and their mimetics via 1,2-oxazines. Chem. Soc. Rev., 2010, 39(2), 549-557.
[8]
Sukhorukov, A.Y.; Klenov, M.S.; Ivashkin, P.E.; Lesiv, A.V.; Khomutova, Y.A.; Loffe, S.L. A convenient procedure for the synthesis of 3-substituted 5, 6-dihydro-4H-1,2-oxazines from nitroethane. Synthesis, 2007, 1, 97-107.
[9]
Eicher, T.; Hauptmann, S.; Speicher, A. The chemistry of heterocycles:
Structures, reactions, synthesis, and applications, 3rd ed.;
John Wiley & Sons: New Jersy, , 2013.
[10]
George, M.; Joseph, L.; Sadanandan, H.R. A review on screening of novel oxazine derivatives for certain pharmacological activities. Ijppr. Human, 2016, 6, 1-6.
[11]
Yakovlev, I.P.; Prep’yalov, A.V.; Ivin, B.A. Unsaturated 4H-1,3-oxazines. Chem. Heterocycl. Compd., 1994, 30, 255-271.
[12]
Prostota, Y.; Berthet, J.; Delbaere, S.; Coelho, P.J. Bichromophoric dye derived from benzo[1,3]oxazine system. Dyes Pigm., 2013, 96, 569-573.
[13]
Herold, P.; Mah, R.; Stutz, S.; Tschinke, V.; Lyothier, I.; Jelakovic, S.; Quirmbach, M.; Marti, C. 2,5-disubstituted piperidines. WIPO
Patent 2007141318A1, 2007.
[14]
Sunil, D.; Upadhya, S.; Rama, M. Synthesis, characterization and QSAR studies of some new 1, 3-oxazines as patent antimicrobial agents. Res. J. Pharma. Sci., 2013, 2(2), 15-19.
[15]
Sauvaître, T.; Barlier, M.; Herlem, D.; Gresh, N.; Chiaroni, A.; Guenard, D.; Guillou, C. New potent acetylcholinesterase inhibitors in the tetracyclic triterpene series. J. Med. Chem., 2007, 50, 5311-5323.
[16]
Li, J.; Tao, H-U. Wang. C.J. Copper(I)/TF-BiphamPhos catalyzed asymmetric nitroso Diels-Alder reaction. Chem. Commun., 2017, 53, 1657-1659.
[17]
Brasholz, M.; Reissig, H-U.; Zimmer, R. Sugars, alkaloids, and heteroaromatics: Exploring heterocyclic chemistry with alkoxyallenes. Acc. Chem. Res., 2009, 42, 45-56.
[18]
Reissig, H.; Zimmer, R.; Medvecký, M.; Linder, I.; Schefzig, L. Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions. Beilstein J. Org. Chem., 2016, 12, 2898-2905.
[19]
Gaonkar, S.L.; Rai, K.M.L. A new method for the generation of α-nitrosoolefins from ketooximes and its application to the synthesis of 5,6-dihydro-4H-1,2-oxazine derivatives. J. Heterocycl. Chem., 2005, 42, 877-881.
[20]
Krupkova, S.; Aguete, G.P.; Kocmanova, L.; Volna, T.; Grepl, M.; Novakova, L.; Miller, M.J.; Hlavac, J. Solid-Phase synthesis of ɤ-lactone and 1,2-oxazine derivatives and their efficient chiral analysis. PLoS One, 2016, 11(11), e0166558.
[21]
Kawade, R.K.; Liu, R.S. Copper-catalyzed three-component annulations of alkenes, nitrosoarenes, and n-hydroxyallylamines to form fused oxazinane/isoxazolidine heterocycles. Angew. Chem. Int. Ed., 2017, 56(8), 2035-2039.
[22]
Sugita, S.; Takeda, N.; Tohnai, N.; Miyata, M.; Miyata, O.; Ueda, M. Gold-catalyzed [3+2]/retro-[3+2]/[3+2] cycloaddition cascade reaction of N-alkoxyazomethine ylides. Angew. Chem. Int. Ed., 2017, 56, 2469-2472.
[23]
Fountoulaki, S.; Gkizis, P.L.; Symeonidis, T.S.; Kaminioti, E.; Karina, A.; Tamiolakis, I.; Armatas, G.S.; Lykakis, I.N. Titania-supported gold nanoparticles catalyze the selective oxidation of amines into nitroso compounds in the presence of hydrogen peroxide. Adv. Synth. Catal., 2016, 358, 1500-1508.
[24]
Zhao, D.; Johansson, M.; Bäckvall, J.E. In situ generation of nitroso compounds from catalytic hydrogen peroxide oxidation of primary aromatic amines and their one-pot use in Hetero-Diels-Alder reactions. Eur. J. Org. Chem., 2007, 2007(26), 4431-4436.
[25]
Andreini, M.; Paolis, M.; Chataigner, I. Thiourea-catalyzed dearomatizing [4 + 2]cycloadditions of 3-nitroindole. Catal., 2015, 63, 15-20.
[26]
Monbaliu, J.M.R.; Cukalovic, A.; Marchand-Brynaert, J.; Stevens, C.V. Straightforward hetero Diels-Alder reaction of nitroso dienophiles by microreactor technology. Tetrahedron Lett., 2010, 51(44), 5830-5833.
[27]
Mikhaylov, A.A.; Dilman, A.D.; Novikov, R.A.; Khoroshutina, Y.A.; Struchkova, M.I.; Arkhipov, D.E.; Nelyubina, Y.V.; Tabolin, A.A.; Ioffe, S.L. Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes. Tetrahedron Lett., 2016, 57(1), 11-14.
[28]
Frazier, C.P.; Bugarin, A.; Engelking, J.R.; de Alaniz, J.R. Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: Efficient and practical accessto nitroso compounds. Org. Lett., 2012, 14(14), 3620-3623.
[29]
Werner, L.; Hudlicky, J.R.; Wernerova, M.; Hudlicky, T. Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines. Tetrahedron, 2010, 66(21), 3761-3769.
[30]
Memeo, M.G.; Lapolla, F.; Maga, G.; Quadrelli, P. Synthesis and antiviral activity of anthracene derivatives of isoxazolino-carbocyclic nucleoside analogs. Tetrahedron Lett., 2015, 56, 1986-1990.
[31]
Xinfang, X.; Doyle, M.P. The [3 + 3]-cycloaddition alternative for heterocycle syntheses: Catalytically generated metalloenolcarbenes as dipolar adducts. Acc. Chem. Res., 2014, 47, 1396-1405.
[32]
Gaonkar, S.L.; Rai, K.M.L. Synthesis of fused-oxazines from cyclic ketoximes via α-nitrosoalkenes. Orient. J. Chem., 2017, 33, 893-896.
[33]
Lonca, G.H.; Tejo, C.; Chan, H.L.; Chiba, S.; Gagosz, F. Gold(I)-catalyzed 6-endo-dig azide–yne cyclization: Efficient access to 2H-1,3-oxazines. Chem. Commun., 2017, 53, 736-739.
[34]
Mollo, M.C.; Orelli, L.R. Microwave-assisted synthesis of 2-aryl-2-oxazolines, 5,6-dihydro-4H-1,3-oxazines, and 4,5,6,7-tetrahydro-1,3-oxazepines. Org. Lett., 2016, 18, 6116-6119.
[35]
De Brito, M.R.M.; Peláez, W.J.; Faillace, M.S.; Militao, G.C.G.; Almeida, J.R.G.S.; Arguello, G.A.; Szakonyi, Z.; Fulop, F.; Salvadori, M.C.; Teixeira, F.S.; Freitas, R.M.; Pinto, P.L.S.; Mengarda, A.C.; Silva, M.P.N.; Da Silva Filho, A.A.; Moraes, J. Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects. Toxicol. In Vitro, 2017, 44, 273-279.
[36]
El-Bayouki, K.A.M.; Basyouni, W.M.; Khatab, T.K.; Kandel, E.M.; Badawy, D.S.; Abdel-Galil, E.; El-Henawy, A.A. Efficient one-pot synthesis, antimicrobial and docking studies of some newer tetrahydro-4H-benzo [1,3-e]oxazines and related β-acylamino ketone derivatives. J. Heterocycl. Chem., 2016, 54, 1054-1064.
[37]
Krishna, P.R.; Ranjith, J.; Rajesh, N.; Sridhar, B. Intramolecular oxyacetoxylation of N-allylamides: An expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride–pyridine system. Org. Biomol. Chem., 2016, 14, 10074-10079.
[38]
Kumaraswamy, K.C.; Shiva Kumari, A.L.; Reddy, A.S. Transition metal-free cascade cyclization of epoxy-ynamides: To go for 1,3-oxazines or 1,4-oxazines? Org. Lett., 2016, 18, 5752-5755.
[39]
Li, P.H.; Yang, J.M.; Wei, Y. Silver(I)-catalyzed intramolecular cyclizations of epoxide-propargylic esters to 1,4-oxazine derivatives. Chem. Open, 2017, 6, 21-24.
[40]
Lee, S.; Ko, Y.O.; Jeon, H.J.; Jung, D.J.; Kim, U.B. Rh(II)/Mg(OtBu)2-catalyzed tandem one-pot synthesis of 1,4-oxazepines and 1,4-oxazines from N-sulfonyl-1,2,3-triazoles and glycidols. Org. Lett., 2016, 18(24), 6432-6435.
[41]
Nejib, H.M. A simple and efficient intramolecular 1,3-dipolar azidoalkyne cycloaddition: Synthesis of 6-perfluoroalkylated fused exo-bicyclic 1,2,3-triazolo-1,4-oxazines. J. Florine Chem., 2016, 186, 97-100.
[42]
Soural, M.; Králová, P.; Fülöpová, V.; Malon, M.; Volná, T.; Popa, I. Stereoselective polymer-supported synthesis of morpholine- and thiomorpholine-3-carboxylic acid derivatives. ACS Comb. Sci., 2017, 19(3), 173-180.
[43]
Anderson, L.L.; Son, J.; Kim, K.H.; Dong-Liang, M.; Wing, D.J. Single-step modular synthesis of unsaturated morpholine N-oxides and their cycloaddition reactions. Angew. Chem. Int. Ed., 2017, 56, 3059-3063.
[44]
Claveau, E.; Gillaizeau, I.; Blu, J.; Bruel, A.; Coudert, G. Easy access to new heterocyclic systems: 1,4-Oxazine and substituted 1,4-oxazines. J. Org. Chem., 2007, 72, 4832-4836.
[45]
Jaya, K.V.; Wan-Ping, H.; Hsing-Yin, C.; Gopal, C.S.; Chung-Yu, C.; Jeh-Jeng, W. A new approach to 1,4-oxazines and 1,4-oxazepines via base-promoted exo mode cyclization of alkynyl alcohols: Mechanism and DFT Studies. Org. Lett., 2012, 14, 3134-3137.
[46]
Paramesh, J.; Jajula, K.; Biswanath, D. Synthesis of dihydrobenzo[1,4]oxazines using copper catalyzed intramolecular ring closure reaction. Tetrahedron Lett., 2013, 54, 3453-3456.
[47]
Deb, M.L.; Pegu, C.D.; Borpatra, J.P.; Baruah, P.K. Metal-free intramolecular α-sp3 C–H oxygenation of tert-amine: An efficient approach to 1,3-oxazines. Tetrahedron Lett., 2016, 57, 5479-5483.
[48]
Kategaonkar, A.H.; Sonar, S.S.; Shelke, S.K.; Shingate, B.B.; Shingare, M.S. Ionic liquid catalyzed multicomponent synthesis of 3,4-dihydro-3-substituted-2H-naphtho[2,1-e][1,3]oxazine derivatives. Org. Commun., 2010, 3, 1-7.
[49]
Ghomi, J.S.; Zahedi, S.; Ghasemzadeh, M.A. Nano silica supported ferric chloride as a green and efficient catalyst for one pot synthesis of 1, 2-dihydro-1-arylnaphtho [1, 2-e][1, 3] oxazine-3-ones. Iran. J. Catal., 2012, 2(1), 27-30.
[50]
Borpatra, P.J.; Deb, M.L.; Baruah, P.K. Visible light prompted metal-free intramolecular dehydrogenative coupling approach to 1,3-Oxazines. Tetrahedron Lett., 2017, 58, 4006-4010.
[51]
Leitão, M.P.S.; Raju, B.R.; Coutinho, C.S.; Maria, J.S. Synthesis and photophysical studies of new benzo[a]phenoxazinium chlorides as antifungal agents. Tetrahedron Lett., 2016, 47(35), 3936-3941.
[52]
Saleh, T.S.; Al-Bogami, A.S.; Mekky, A.E.M.; Alkhathlan, H.Z. Sonochemical synthesis of novel pyrano[3,4-e][1,3]oxazines: A green protocol. Ultrason. Sonochem., 2017, 36, 474-480.
[53]
Chen, H.; Wu, G.; Lv, T.; Mo, W.; Yang, X.; Gao, Y. One-pot synthesis of tricyclo-1,4-benzoxazines via visible-light photoredox catalysis in continuous flow. Tetrahedron Lett., 2017, 58, 1395-1398.
[54]
Jaiswal, P.K.; Sharma, V.; Prikhodko, J.; Mashevskaya, I.V.; Chaudhary, S. “On water” ultrasound-assisted one pot efficient synthesis of functionalized 2-oxo-benzo[1,4]oxazines: First application to the synthesis of anticancer indole alkaloid, Cephalandole A. Tetrahedron Lett., 2017, 58, 2077-2083.
[55]
Sarmiento-Sánchez, J.I. Montes-Avila, J.; Ochoa-Terán, A.; Delgado-Vargas, F.; Wilson-Corral, V.; Díaz-Camacho, S.P.; García-Páez, F.; Bastidas-Bastidas, P. Synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides: Evaluation of antioxidant and antimicrobial activities. Quim. Nova, 2014, 37(8), 1297-1301.
[56]
Sun, M.; Zhao, J.; Chen, X.; Zong, Z.; Han, J.; Du, Y.; Sun, H.; Wang, F. Synthesis and biological evaluation of novel tricyclic oxazine and oxazepine fused quinazolines. Part 2: Gefitinib analogs. Bioorg. Med. Chem. Lett., 2016, 26, 4842-4845.
[57]
Waghmode, N.A.; Kalbandhe, A.H.; Thorat, P.B.; Karade, N.N. Metal-free new synthesis of 1,3-naphthoxazines via intramolecular cross dehydrogenative-coupling reaction of 1-(α-aminoalkyl)-2-naphthols using hypervalent iodine(III) reagent. Tetrahedron Lett., 2016, 57, 680-683.
[58]
Kiskan, B.; Yusuf, Y. Synthesis and characterization of naphthoxazine functional poly(ε-caprolactone). Polymer, 2005, 46, 11690-11697.
[59]
Morrison, R.; Zheng, Z.; Jennings, G.; Thompson, P.E.; Al-Rawi, J.M. Synthesis of linear and angular aryl-morpholino-naphth-oxazines, their DNA-PK, PI3K, PDE3A and antiplatelet activity. Bioorg. Med. Chem. Lett., 2016, 26, 5534-5538.
[60]
Lin, A.; Russell, C.; Baker, J.R.; Frailey, S.L.; Sakoff, J.; McCluskey, A. A facile hybrid ‘flow and batch’ access to substituted 3,4-dihydro-2H-benzo[b][1,4]oxazinones. Org. Biomol. Chem., 2016, 14, 8732-8742.
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