Lewis Acid-Mediated Efficient Synthesis of 4H-1,3-benzo-xazines and Their Derivatives 4,5-dihydro-1,3-benzo-xazepines

(a)Taylor, A.P.; Robinson, R.P.; Fobian, Y.M.; Blakemore, D.C.; Jones, L.H.; Fadeyi, O. Modern advances in heterocyclic chemistry in drug discovery. Org. Biomol. Chem., 2016, 14(28), 6611-6637.
[http://dx.doi.org/10.1039/C6OB00936K] [PMID: 27282396]
(b)Chen, Z.P.; Zhou, Y.G. Asymmetric hydrogenation of heteroarenes with multiple heteroatoms. Synthesis, 2016, 48, 1769-1781.
[http://dx.doi.org/10.1055/s-0035-1561622]
(c)Rohokale, R.S.; Kshirsagar, U.A. Advanced synthetic strategies for constructing quinazolinone scaffolds. Synthesis, 2016, 48, 1253-1260.
[http://dx.doi.org/10.1055/s-0035-1560413]
(d)Cabrele, C.; Reiser, O. The modern face of synthetic heterocyclic chemistry. J. Org. Chem., 2016, 81(21), 10109-10125.
[http://dx.doi.org/10.1021/acs.joc.6b02034] [PMID: 27680573]
(e)Luo, Y.; Li, B.; Wang, W.; Wu, K.; Tan, B. Hypercrosslinked aromatic heterocyclic microporous polymers: a new class of highly selective CO2 capturing materials. Adv. Mater., 2012, 24(42), 5703-5707.
[http://dx.doi.org/10.1002/adma.201202447] [PMID: 23008146]
(f)Ryu, D.; Mouchiroud, L.; Andreux, P.A.; Katsyuba, E.; Moullan, N.; Félix, A.A.N.; Williams, E.G.; Jha, P.; Lo Sasso, G.; Huzard, D.; Aebischer, P.; Sandi, C.; Rinsch, C.; Auwerx, J. Urolithin A induces mitophagy and prolongs lifespan in C. elegans and increases muscle function in rodents. Nat. Med., 2016, 22(8), 879-888.
[http://dx.doi.org/10.1038/nm.4132] [PMID: 27400265]

(a)Gandini, A.; Lacerda, T.M.; Carvalho, A.J.F.; Trovatti, E. Progress of polymers from renewable resources: furans, vegetable oils, and polysaccharides. Chem. Rev., 2016, 116(3), 1637-1669.
[http://dx.doi.org/10.1021/acs.chemrev.5b00264] [PMID: 26291381]
(b)Chinnappan, A.; Baskar, C.; Kim, H. Biomass into chemicals: green chemical conversion of carbohydrates into 5-hydroxymethylfurfural in ionic liquids. RSC Adv., 2016, 6, 63991-64002.
[http://dx.doi.org/10.1039/C6RA12021K]
(c)Clark, J.H.; Farmer, T.J.; Hunt, A.J.; Sherwood, J. Opportunities for bio-based solvents created as petrochemical and fuel products transition towards renewable resources. Int. J. Mol. Sci., 2015, 16(8), 17101-17159.
[http://dx.doi.org/10.3390/ijms160817101] [PMID: 26225963]
(d)Rodrigues, T.; Reker, D.; Schneider, P.; Schneider, G. Counting on natural products for drug design. Nat. Chem., 2016, 8(6), 531-541.
[http://dx.doi.org/10.1038/nchem.2479] [PMID: 27219696]
(e)Brown, L.E.; Konopelski, J.P. Turning the corner: recent advances in the synthesis of the welwitindolinones. Org. Prep. Proced. Int., 2008, 40, 411-445.
[http://dx.doi.org/10.1080/00304940809458104]
(f)Tan, L.P.; Wu, H.; Yang, P-Y.; Kalesh, K.A.; Zhang, X.; Hu, M.; Srinivasan, R.; Yao, S.Q. High-throughput discovery of Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) inhibitors using click chemistry. Org. Lett., 2009, 11(22), 5102-5105.
[http://dx.doi.org/10.1021/ol9023419] [PMID: 19852491]
(g)Boiani, M.; González, M. Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini Rev. Med. Chem., 2005, 5(4), 409-424.
[http://dx.doi.org/10.2174/1389557053544047] [PMID: 15853629]
(h)Bignan, G.C.; Battista, K.; Connolly, P.J.; Orsini, M.J.; Liu, J.; Middleton, S.A.; Reitz, A.B. Preparation of 3-spirocyclic indolin-2-ones as ligands for the ORL-1 receptor. Bioorg. Med. Chem. Lett., 2005, 15(22), 5022-5026.
[http://dx.doi.org/10.1016/j.bmcl.2005.08.009] [PMID: 16153834]
(i)Yurchenko, R.I.; Ponomarenko, A.D.; Svarovskaya, N.N. 2-(Adamantan-1-yl) imidazo [1, 2-a] pyridines and their Derivatives. Chem. Heterocycl. Compd., 2005, 41, 656-661.
[http://dx.doi.org/10.1007/s10593-005-0198-0]
(j)Ueda, T.; Mizushige, K.; Yukiiri, K.; Takahashi, T.; Kohno, M. Improvement of cerebral blood flow by olprinone, a phosphodiesterase-3 inhibitor, in mild heart failure. Cerebrovasc. Dis., 2003, 16(4), 396-401.
[http://dx.doi.org/10.1159/000072563] [PMID: 13130181]
(k)Hecker, E. Cocarcinogenic principles from the seed oil of Croton tiglium and from other Euphorbiaceae. Cancer Res., 1968, 28(11), 2338-2349.
[PMID: 5723975]

(a)indhu, 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.
(b)Tietze, L.F. Domino reactions in organic synthesis. Chem. Rev., 1996, 96(1), 115-136.
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
(c)Laobuthee, A.; Chirachanchai, S.; Ishida, H.; Tashiro, K. Asymmetric mono-oxazine: an inevitable product from Mannich reaction of benzoxazine dimers. J. Am. Chem. Soc., 2001, 123(41), 9947-9955.
[http://dx.doi.org/10.1021/ja004048o] [PMID: 11592873]

(a)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.
(b)Yakovlev, I.P.; Prep’yalov, A.V.; Ivin, B.A. Unsaturated 4H-1, 3-oxazines. Heterocycl. Compd., 1994, 30, 255-271.
[http://dx.doi.org/10.1007/BF01165688]
(c)Prostota, Y.; Berthet, J.; Delbaere, S.; Coelho, P.J. Bichromophoric dye derived from benzo [1, 3] oxazine system. Dyes Pigm., 2013, 96, 569-573.
[http://dx.doi.org/10.1016/j.dyepig.2012.09.017]

(a)Gaonkar, S.L.; Nagaraj, V.U.; Nayak, S. A review on current synthetic strategies of oxazines. Mini Rev. Org. Chem., 2019, 16(1), 43-58.
[http://dx.doi.org/10.2174/1570193X15666180531092843]
(b)Vibhute, A.Y.; Zangade, S.B.; Chavan, S.B.; Vibhute, Y.B. Pelagia research library. Pharm. Sin., 2011, 2, 217-222.
(c)Siddiqui, N.; Ali, R.; Alam, M.S.; Ahsan, W. Pharmacological profile of benzoxazines: a short review. J. Chem. Pharm. Res., 2010, 2, 309-316.

(a)Ishida, H.; Agag, T. Handbook of Benzoxazine Resins; Elsevier Publication, 2011.
(b)Fang, B.; Lu, X.; Hu, J.; Zhang, G.; Zheng, X.; He, L.; Cao, J.; Gu, J.; Cao, F. pH controlled green luminescent carbon dots derived from benzoxazine monomers for the fluorescence turn-on and turn-off detection. J. Colloid Interface Sci., 2019, 536, 516-525.
[http://dx.doi.org/10.1016/j.jcis.2018.10.088] [PMID: 30388529]

(a)Qiang, L.G.; Baine, N.H. A convenient synthesis of substituted quinolines by thermal or photochemical electrocyclic rearrangement of o-vinyl imidates under non-acidic conditions. Tetrahedron Lett., 1988, 29, 3517-3520.
[http://dx.doi.org/10.1016/0040-4039(88)85281-X]
(b)Capozzi, Giuseppe; Ottana, Rosaria; Romeo, Giovanni; Valle, Giovanni. Intramolecular cyclization using methylbis(methylthio)sulfonium salts. Part 3. Synthesis of 3,1-benzo-xazines. J. Chem. Res. Synop., 1986, 6, 200-201.

(a)Tsoungas, P.G. Synthesis of 1, 2-oxazines and their N-oxides. Heterocycles, 2002, 57, 1149-1178.
[http://dx.doi.org/10.3987/REV-02-547]
(b)Varela, J.A.; Saa, C. Metal-catalyzed cyclizations to pyran and oxazine derivatives. Synthesis, 2016, 48, 3470-3478.
[http://dx.doi.org/10.1055/s-0035-1562466]
(c)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.
[http://dx.doi.org/10.2174/1570179411666140623230529]
(d)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.
(e)Pfrengle, F.; Reissig, H.U. Amino sugars and their mimetics via 1,2-oxazines. Chem. Soc. Rev., 2010, 39(2), 549-557.
[http://dx.doi.org/10.1039/B914356D] [PMID: 20111779]
(f)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, 97-107.

(a)Liu, Y.; Zhao, S.; Wang, H.; Run, M. Synthesis, polymerization, and thermal properties of benzoxazine based on p-aminobenzonitrile. Thermochim. Acta, 2012, 549, 42-48.
[http://dx.doi.org/10.1016/j.tca.2012.09.017]
(b)Bendorf, H.D.; Vebrosky, E.N.; Eck, B.J. Synthesis and characterization of 1, 4-dihydro-3, 1-benzoxazines and 1, 2, 3, 4-tetrahydroquinazolines: an unknown structure determination experiment. J. Chem. Educ., 2016, 93, 1637-1641.
[http://dx.doi.org/10.1021/acs.jchemed.6b00155]
(c)Han, B.; Yang, X.L.; Wang, C.; Bai, Y.W.; Pan, T.C.; Chen, X.; Yu, W. CuCl/DABCO/4-HO-TEMPO-catalyzed aerobic oxidative synthesis of 2-substituted quinazolines and 4H-3,1-benzoxazines. J. Org. Chem., 2012, 77(2), 1136-1142.
[http://dx.doi.org/10.1021/jo2020399] [PMID: 22168403]
(d)Butler, J.D.; Solano, D.M.; Robins, L.I.; Haddadin, M.J.; Kurth, M.J. A facile synthesis of new 5H-indazolo[3,2-b]benzo[d]-1,3-oxazines via one-pot intramolecular bis-heterocyclizations. J. Org. Chem., 2008, 73(1), 234-240.
[http://dx.doi.org/10.1021/jo702067z] [PMID: 18052193]

(a)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. (Camb.), 2017, 53(4), 736-739.
[http://dx.doi.org/10.1039/C6CC08397H] [PMID: 27990524]
(b)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.
[http://dx.doi.org/10.1002/jhet.2674]
(c)Cai, Z.J.; Li, F.H.; Wang, S.Y.; Ji, S.J. Palladium-catalyzed cascade arene/alkyne annulation: synthesis of fluorene-benzoxazine derivatives. Org. Lett., 2016, 18(19), 4810-4813.
[http://dx.doi.org/10.1021/acs.orglett.6b02224] [PMID: 27616460]

(a)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(23), 6116-6119.
[http://dx.doi.org/10.1021/acs.orglett.6b03122] [PMID: 27934376]
(b)de Brito, M.R.M.; Peláez, W.J.; Faillace, M.S.; Militão, G.C.G.; Almeida, J.R.G.S.; Argüello, G.A.; Szakonyi, Z.; Fülöp, 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.; de Moraes, J. Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects. Toxicol. In Vitro, 2017, 44, 273-279.
[http://dx.doi.org/10.1016/j.tiv.2017.07.021] [PMID: 28755871]
(c)Ranjith, J.; Rajesh, N.; Sridhar, B.; Radha Krishna, P. 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(42), 10074-10079.
[http://dx.doi.org/10.1039/C6OB01752E] [PMID: 27722637]
(d)Wang, J.; Zhou, R.; Zhuang, S.; Wu, A. Acid-mediated four-component tandem cyclization: access to multifused 1, 3-benzoxazine frameworks. Tetrahedron, 2018, 74, 7283-7289.
[http://dx.doi.org/10.1016/j.tet.2018.10.059]

(a)Maity, A.; Teets, T.S. Main group Lewis acid-mediated transformations of transition-metal hydride complexes. Chem. Rev., 2016, 116(15), 8873-8911.
[http://dx.doi.org/10.1021/acs.chemrev.6b00034] [PMID: 27164024]
(b)North, M.; Usanov, D.L.; Young, C. Lewis acid catalyzed asymmetric cyanohydrin synthesis. Chem. Rev., 2008, 108(12), 5146-5226.
[http://dx.doi.org/10.1021/cr800255k] [PMID: 19067648]
(c)Mahrwald, R. Diastereoselection in Lewis-acid-mediated aldol additions. Chem. Rev., 1999, 99(5), 1095-1120.
[http://dx.doi.org/10.1021/cr980415r] [PMID: 11749441]
(d)Hong, M.; Chen, J.; Chen, E.Y.X. Polymerization of polar monomers mediated by main-group Lewis acid-base pairs. Chem. Rev., 2018, 118(20), 10551-10616.
[http://dx.doi.org/10.1021/acs.chemrev.8b00352] [PMID: 30350583]
(e)Kessar, S.V.; Singh, P. Lewis acid complexation of tertiary amines and related compounds: a strategy for α-deprotonation and stereocontrol. Chem. Rev., 1997, 97(3), 721-738.
[http://dx.doi.org/10.1021/cr950082n] [PMID: 11848886]
(f)Liu, L.L.; Stephan, D.W. Radicals derived from Lewis acid/base pairs. Chem. Soc. Rev., 2019, 48(13), 3454-3463.
[http://dx.doi.org/10.1039/C8CS00940F] [PMID: 30724924]
(g)Liu, Y.; Lau, T.C. Activation of metal oxo and nitrido complexes by Lewis acids. J. Am. Chem. Soc., 2019, 141(9), 3755-3766.
[http://dx.doi.org/10.1021/jacs.8b13100] [PMID: 30707842]
(h)Bayne, J.M.; Stephan, D.W. Phosphorus Lewis acids: emerging reactivity and applications in catalysis. Chem. Soc. Rev., 2016, 45(4), 765-774.
[http://dx.doi.org/10.1039/C5CS00516G] [PMID: 26255595]
(i)Cañeque, T.; Truscott, F.M.; Rodriguez, R.; Maestri, G.; Malacria, M. Electrophilic activation of allenenes and allenynes: analogies and differences between Brønsted and Lewis acid activation. Chem. Soc. Rev., 2014, 43(9), 2916-2926.
[http://dx.doi.org/10.1039/C4CS00023D] [PMID: 24643348]
(j)Lichtenberg, C.; Pan, F.; Spaniol, T.P.; Englert, U.; Okuda, J. The bis(allyl)bismuth cation: a reagent for direct allyl transfer by Lewis acid activation and controlled radical polymerization. Angew. Chem. Int. Ed. Engl., 2012, 51(52), 13011-13015.
[http://dx.doi.org/10.1002/anie.201206782] [PMID: 23166056]
(k)Bai, Y.; Tao, W.; Ren, J.; Wang, Z. Lewis acid catalyzed intramolecular [4+2] and [3+2] cross-cycloaddition of alkynylcyclopropane ketones with carbonyl compounds and imines. Angew. Chem. Int. Ed. Engl., 2012, 51(17), 4112-4116.
[http://dx.doi.org/10.1002/anie.201200450] [PMID: 22407901]
(l)Denmark, S.E.; Beutner, G.L.; Wynn, T.; Eastgate, M.D. Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes. J. Am. Chem. Soc., 2005, 127(11), 3774-3789.
[http://dx.doi.org/10.1021/ja047339w] [PMID: 15771512]
(m)Corma, A.; García, H. Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem. Rev., 2003, 103(11), 4307-4365.
[http://dx.doi.org/10.1021/cr030680z] [PMID: 14611265]

Wang, Y-M.; Wu, J.; Hoong, C.; Rauniyar, V.; Toste, F.D. Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis. J. Am. Chem. Soc., 2012, 134(31), 12928-12931.
[http://dx.doi.org/10.1021/ja305795x] [PMID: 22830953]

Jana, S.; Ashokan, A.; Kumar, S.; Verma, A.; Kumar, S. Copper-catalyzed trifluoromethylation of alkenes: synthesis of trifluoromethylated benzoxazines. Org. Biomol. Chem., 2015, 13(31), 8411-8415.
[http://dx.doi.org/10.1039/C5OB01196E] [PMID: 26166814]

Xia, H.D.; Zhang, Y.D.; Wang, Y.H.; Zhang, C. Water-soluble hypervalent Iodine(III) having an I-N bond. A reagent for the synthesis of indoles. Org. Lett., 2018, 20(13), 4052-4056.
[http://dx.doi.org/10.1021/acs.orglett.8b01615] [PMID: 29911872]

Du, W.; Gu, Q.; Li, Z.; Yang, D. Palladium(II)-catalyzed intramolecular tandem aminoalkylation via divergent C(sp3)-H functionalization. J. Am. Chem. Soc., 2015, 137(3), 1130-1135.
[http://dx.doi.org/10.1021/ja5102739] [PMID: 25541675]

Pereira, G.J.V.; Tavares, M.T.; Azevedo, R.A.; Martins, B.B.; Cunha, M.R.; Bhardwaj, R.; Cury, Y.; Zambelli, V.O.; Barbosa, E.G.; Hediger, M.A.; Filho, R.P. Capsaicin-like analogue induced selective apoptosis in A2058 melanoma cells: design, synthesis and molecular modeling. Bioorg. Med. Chem., 2019, 27(13), 2893-2904.
[http://dx.doi.org/10.1016/j.bmc.2019.05.020] [PMID: 31104785]

Wang, Y.F.; Chen, H.; Zhu, X.; Chiba, S. Copper-catalyzed aerobic aliphatic C-H oxygenation directed by an amidine moiety. J. Am. Chem. Soc., 2012, 134(29), 11980-11983.
[http://dx.doi.org/10.1021/ja305833a] [PMID: 22789112]

Zimaity, T.; Anwar, M.; Abdel, I. Study of the reaction of Grignard reagents with 4(3H)-quinazolinones and 4H-3,1-benzoxazin-4-ones. Acta Chir. Acad. Sci. Hung., 1975, 87(3), 251-255.

Qiang, L.G.; Baine, N.H. A convenient synthesis of substituted quinolines by thermal electrocyclic rearrangement of o-vinyl anils under nonacidic conditions. J. Org. Chem., 1988, 53(18), 4218-4222.
[http://dx.doi.org/10.1021/jo00253a011]

Katritzky, A.R.; Zhang, G.; Jiang, J.; Steel, P.J. A novel o-iminophenyl anion route to heterocycles and ortho-substituted anilines. J. Org. Chem., 1995, 60(23), 7625-7630.
[http://dx.doi.org/10.1021/jo00128a040]