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Mini-Reviews in Organic Chemistry

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ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Review Article

A Review on Current Synthetic Strategies of Oxazines

Author(s): Santosh L. Gaonkar*, Vignesh U. Nagaraj and Swarnagowri Nayak

Volume 16, Issue 1, 2019

Page: [43 - 58] Pages: 16

DOI: 10.2174/1570193X15666180531092843

Price: $65

Abstract

In the past three decades, the heterocyclic oxazine cores have been intensely concerned. Oxazine derivatives are promising vital heterocyclic motifs. They are eminent for their synthetic potential and extensive biological properties. Oxazines are versatile intermediates for the synthesis of a variety of heterocycles and bifunctional compounds. Researchers have reported several synthetic approaches for the preparation of oxazines. This review emphasises the recent approaches for the synthesis of oxazine derivatives.

Keywords: Diels-Alder reactions, cross-coupling reactions, 1, 2-oxazines, 1, 3-oxazines, 1, 4-oxazines, fused oxazines.

Graphical Abstract

[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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