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Journal articles on the topic '2-oxazines'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Thirunarayanan, Ganesamoorthy, V. Renuka, K. G. Sekar, K. Lakshmanan, and K. Anbarasu. "Insect Antifeedant Potent Unsaturated 1,3-Oxazine-2-Amines." International Letters of Chemistry, Physics and Astronomy 23 (November 2013): 66–81. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.23.66.

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Insect antifeedant activities of some halo substituted aryl 1,3-oxazine-2-amines have been measured using 4th instar larvae Achoea janata L by castor leaf discs-Dethler’s method. The highly halo substituted oxazine amines have shown good insect antifeedant activities. The 1,3-oxazine amines have been synthesised by greener method by solvent-free cyclization of aryl enones with urea under microwave irradiation. The yields of the oxazines were more than 80%. The synthesised oxazines were characterized by their physical constants, analytical and spectroscopic data.

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2

Kirila, Tatyana, Anna Smirnova, Vladimir Aseyev, Andrey Tenkovtsev, Heikki Tenhu, and Alexander Filippov. "Self-Organization in Dilute Aqueous Solutions of Thermoresponsive Star-Shaped Six-Arm Poly-2-Alkyl-2-Oxazines and Poly-2-Alkyl-2-Oxazolines." Polymers 13, no. 9 (2021): 1429. http://dx.doi.org/10.3390/polym13091429.

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The behavior of star-shaped six-arm poly-2-alkyl-2-oxazines and poly-2-alkyl-2-oxazolines in aqueous solutions on heating was studied by light scattering, turbidimetry and microcalorimetry. The core of stars was hexaaza [26] orthoparacyclophane and the arms were poly-2-ethyl-2-oxazine, poly-2-isopropyl-2-oxazine, poly-2-ethyl-2-oxazoline, and poly-2-isopropyl-2-oxazoline. The arm structure affects the properties of polymers already at low temperatures. Molecules and aggregates were present in solutions of poly-2-alkyl-2-oxazines, while aggregates of two types were observed in the case of poly-

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3

Dawood, Kamal M., Thoraya A. Farghaly, and Mohamed A. Raslan. "Heteroannulation Routes to Bioactive Pyrazolooxazines." Current Organic Chemistry 24, no. 17 (2020): 1943–75. http://dx.doi.org/10.2174/1570179417999200628035124.

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Pyrazolo-oxazine fused systems are interesting classes of heterocyclic compounds exhibiting pronounced biological applications such as anticancer, antitubercular, anti-inflammatory, antibacterial and antifungal activities as well as inhibiting COX-1 and COX-2 enzymes. Depending on the distribution position of the heteroatoms (N and O), there are fourteen different systems of pyrazolo-oxazine. Nine of them were biologically abundant in literature, for example, pyrazolo[3,4-e][1,3]oxazines are used as analogs of antibiotics Formycin, Formycin B, Oxoformycin B. This review article summarizes the

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4

Kirila, Tatyana, Anna Smirnova, Alla Razina, Andrey Tenkovtsev, and Alexander Filippov. "Influence of Salt on the Self-Organization in Solutions of Star-Shaped Poly-2-alkyl-2-oxazoline and Poly-2-alkyl-2-oxazine on Heating." Polymers 13, no. 7 (2021): 1152. http://dx.doi.org/10.3390/polym13071152.

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The water–salt solutions of star-shaped six-arm poly-2-alkyl-2-oxazines and poly-2-alkyl-2-oxazolines were studied by light scattering and turbidimetry. The core was hexaaza[26]orthoparacyclophane and the arms were poly-2-ethyl-2-oxazine, poly-2-isopropyl-2-oxazine, poly-2-ethyl-2-oxazoline, and poly-2-isopropyl-2-oxazoline. NaCl and N-methylpyridinium p-toluenesulfonate were used as salts. Their concentration varied from 0–0.154 M. On heating, a phase transition was observed in all studied solutions. It was found that the effect of salt on the thermosensitivity of the investigated stars depen

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5

Cherton, Jean-Claude, Paul-Louis Desbene, Marc Bazinet, Marc Lanson, Odile Convert, and Jean-Jacques Basselier. "Réactivité du nucléophile azoture vis à vis de cations hétérocycliques aromatiques. VI. Cas des triaryl-2,4,6 oxaziniums-1,3." Canadian Journal of Chemistry 63, no. 1 (1985): 86–94. http://dx.doi.org/10.1139/v85-015.

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Nucleophilic attack of sodium azide on 2,4,6-triaryl-1,3-oxazinium species gives high yields of β-tetrazolo-trans-benzalacetophenones from the corresponding 2-azido-1,3-oxazines. The rearrangement of the azido oxazines likely proceeds via tautomerism of the intermediate iminoazides. If the formation of the 2-azido-1,3-oxazines is under kinetic control, these results are a rare example of high regioselectivity in nucleophilic attack at the C2 carbon of 1,3-oxazinium species.The reaction behaviour of the 1,3-oxazinium/N3− system is discussed, together with results obtained from the 2,4,6-triphen

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6

Vorbrüggen, Helmut, та Konrad Krolikiewicz. "A simple synthesis of Δ2-oxazines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles". Tetrahedron 49, № 41 (1993): 9353–72. http://dx.doi.org/10.1016/0040-4020(93)80021-k.

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7

Couture, Philippe, та John Warkentin. "Spiro-fused 2-alkoxy-2-amino-Δ3-1,3,4-oxadiazolines. Synthesis and thermolysis to corresponding aminooxycarbenes". Canadian Journal of Chemistry 75, № 9 (1997): 1264–80. http://dx.doi.org/10.1139/v97-153.

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Δ3-1,3,4-Oxadiazolines spiro-fused at C2 to C2 to oxazolidines (12) or to C2 of tetrahydro-1,3-oxazines (13) were synthesized. The oxadiazolines undergo thermolysis in benzene at 90 °C with first-order rate constants of (1.6–50) × 10−5 s−1. The dependence of these rate constants on the nature of the substituents present on the oxadiazoline ring is consistent with a mechanism involving a carbonyl ylide intermediate. Substituents on N of the oxazolidine or tetrahydro-1,3-oxazine moieties play a major role in determining the fragmentation pathways. Oxadiazolines with N-carbonyl groups (12c–j, 13d

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8

Sana, Michel, Georges Leroy, Jean-Luc Vaerman, and Heinz Gunter Viehe. "The thermal isomerization of bicyclic oxazines into epoxyepimines. A preliminary theoretical study." Canadian Journal of Chemistry 68, no. 9 (1990): 1625–28. http://dx.doi.org/10.1139/v90-251.

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The thermal isomerization of bicyclic oxazines 1 to epoxyepimines 2 depends on the N-substituent. BDE calculations on model systems agree with the mechanistic picture. The rate-determining step in N—O bond homolysis is facilitated by N-vinyl substituents. Keywords: oxazines, BDE, NO bond, substituent effect.

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9

Kirila, Tatyana, Anna Smirnova, Alla Razina, Andrey Tenkovtsev, and Alexander Filippov. "Synthesis and Conformational Characteristics of Thermosensitive Star-Shaped Six-Arm Polypeptoids." Polymers 12, no. 4 (2020): 800. http://dx.doi.org/10.3390/polym12040800.

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Star-shaped six-arm poly-2-alkyl-2-oxazine and poly-2-alkyl-2-oxazoline with hexaaza [26]orthoparacyclophane derivative core were synthesized successfully using cationic ring-opening polymerization. Conformational behavior of prepared polymer stars were investigated by the methods of molecular hydrodynamics and optics in molecular dispersed solutions. It was shown that conformation characteristics of star-shaped polypeptoids depends on arm length, while the chemical structure weakly affects the behavior of the studied polymers in solutions. This behavior is caused by the close equilibrium rigi

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10

Khlebnikov, Alexander F., Mikhail S. Novikov, Yelizaveta G. Gorbunova, et al. "Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines." Beilstein Journal of Organic Chemistry 10 (August 14, 2014): 1896–905. http://dx.doi.org/10.3762/bjoc.10.197.

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Theoretical and experimental studies of the reaction of isoxazoles with diazo compounds show that the formation of 2H-1,3-oxazines proceeds via the formation of (3Z)-1-oxa-5-azahexa-1,3,5-trienes which undergo a 6π-cyclization. The stationary points corresponding to the probable reaction intermediates, isoxazolium N-ylides, were located by DFT calculations at the B3LYP/6-31G(d) level only for derivatives without a substituent in position 3 of the isoxazole ring. These isoxazolium N-ylides are thermodynamically and kinetically very unstable. According to the calculations and experimental result

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11

Mohammadpoor-Baltork, Iraj, Majid Moghadam, Shahram Tangestaninejad, Valiollah Mirkhani, and Zohre Eskandari. "H3PW12O40: An Efficient and Recyclable Heterogeneous Catalyst for the Selective Synthesis of 2-Aryl-5,6-dihydro-4H-1,3-oxazines and 2-Aryl-1,4,5,6-tetrahydropyrimidines." Zeitschrift für Naturforschung B 65, no. 4 (2010): 461–69. http://dx.doi.org/10.1515/znb-2010-0404.

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An environmentally friendly and highly efficient procedure has been developed for the selective synthesis of 2-aryl-5,6-dihydro-4H-1,3-oxazines and 2-aryl-1,4,5,6-tetrahydropyrimidines by cyclocondensation of arylnitriles with 3-amino-1-propanol and 1,3-diaminopropane in the presence of catalytic amounts of H3PW12O40 under thermal conditions and MW irradiation. Under the same reaction conditions, dicyanobenzenes are transformed to their corresponding mono-oxazines and monotetrahydropyrimidines with excellent chemoselectivity. These reactions are simple and clean, giving the products in high yi

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12

Singh, Kamaljit, Prasant K. Deb, and Sonia Behal. "ChemInform Abstract: 2-Arylsulfinylmethyl Oxazines: Chiral Carbonyl Equivalents." ChemInform 33, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.200208153.

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13

Firpo, Guadalupe, María L. Ramírez, Martín S. Faillace, et al. "Evaluation of the Antioxidant Activity of Cis/Trans-N-Phenyl-1,4,4a,5,8,8a-Hexahydro-3,1-Benzoxazin-2-Imines." Antioxidants 8, no. 6 (2019): 197. http://dx.doi.org/10.3390/antiox8060197.

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The growing interest in the chemistry of unsaturated ring-fused 1,3-heterocycles, in this particular case 1,3-oxazines, arise in part from their versatile pharmacological applications. In the present article, the evaluation of the in vitro and ex vivo antioxidant activity of two cyclohexene-fused oxazines is discussed. The in vitro antioxidant activity was evaluated by trapping the ABTS and hydroxyl radicals as well as the inhibition of the enzyme acetyl-cholinesterase and hemolysis of erythrocytes by 2,2’-Azobis(2-amidinopropane) dihydrochloride (AAPH). The results suggest that both unsaturat

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14

Belz, Tyson, Saleh Ihmaid, Jasim Al-Rawi, and Steve Petrovski. "Synthesis Characterization and Antibacterial, Antifungal Activity of N-(Benzyl Carbamoyl or Carbamothioyl)-2-hydroxy Substituted Benzamide and 2-Benzyl Amino-Substituted Benzoxazines." International Journal of Medicinal Chemistry 2013 (October 31, 2013): 1–20. http://dx.doi.org/10.1155/2013/436397.

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New N-(benzyl carbamothioyl)-2-hydroxy substituted benzamides 13, 20, and 21 were synthesized using sodium bicarbonate and benzyl amine with 2-thioxo-substituted-1,3-benzoxazines 6, 10a, b, 11c, and 12a–n. The 2-thioxo-substituted-1,3-oxazines 6, 10a-b, 11d 12a–n, and 26 were converted to the corresponding 2-methylthio-substituted-1,3-oxazines 14a–l and 24 which were then converted to 2-benzyl amino-substituted-benzoxazines 15a–i by refluxing with benzylamine. Products 15a, b, e, f, and g were also synthesized by boiling the corresponding N-(benzyl carbamothioyl)-2-hydroxy substituted benzamid

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15

Gyamfi, Abigail Owusuwaa, Martin Amponsah Yeboah, Richard Tia, and Evans Adei. "Computational study on the mechanism of transition metal-catalyzed formation of highly substituted furo [3,4-d] [1,2] oxazines." Journal of Theoretical and Computational Chemistry 17, no. 01 (2018): 1850011. http://dx.doi.org/10.1142/s0219633618500116.

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The mechanism of gold(III)-catalyzed 1,3-dipolar [[Formula: see text]] cycloaddition reactions of 2-(1-alkynyl)-2-alken-1-ones with nitrones to afford highly-substituted furo [3,4-d] [1,2] oxazines, which are useful as structural skeletons in biologically active compounds and as synthetic building blocks in organic synthesis, have been studied computationally. The results show that the reaction proceeds via the formation of a [Formula: see text]-complex in which the gold moiety coordinates to the triple bond of the 2-(1-alkynyl)-2-alken-1-ones, resulting in an intramolecular cyclization of the

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16

Lin, Cheng-Tung, and Wen-Jei Hsu. "Study of trichloronitrosomethane: regioselective cycloadditions of 2-substituted-1,3-butadienes." Canadian Journal of Chemistry 67, no. 12 (1989): 2153–61. http://dx.doi.org/10.1139/v89-335.

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The regioselectivity of cycloaddition reactions of trichloronitrosomethane (1) with 2-alkyl (R = Me, Et, i-Pr, t-Bu, CF3, Bz, and Cl) and 2-aryl (Ar = Ph, 4-CH3OPh, 4-CH3Ph, 3-CH3Ph, and 4-ClPh) 1,3-butadienes is described. The orientation of cycloaddition is substituent dependent, producing 2,5-disubstituted (para) and 2,4-disubstituted (meta) 3,6-dihydro-1,2-oxazines from 2-alkyl- and 2-aryl-1,3-butadienes respectively. Increasing the bulk of the substituent from methyl to tert-butyl in 2-alkyl-1,3-butadienes increases the regioselectivity. Kinetic studies in various solvents indicate that p

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17

Anitha, Mandala, Mallepalli Shankar, and K. C. Kumara Swamy. "Reactivity of epoxy-ynamides with metal halides: nucleophile (Br/Cl/OH)-assisted tandem intramolecular 5-exo-digor 6-endo-digcyclisation and AgF2-promoted oxidation." Organic Chemistry Frontiers 6, no. 8 (2019): 1133–39. http://dx.doi.org/10.1039/c9qo00027e.

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18

Cwik, Agnieszka, Zoltán Hell, Adrienn Hegedüs, Zoltán Finta, and Zoltán Horváth. "A simple synthesis of 2-substituted oxazolines and oxazines." Tetrahedron Letters 43, no. 22 (2002): 3985–87. http://dx.doi.org/10.1016/s0040-4039(02)00723-2.

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19

Holzapfel, C. W., G. J. Kruger, and M. S. Van Dyk. "Structures of 3-cyanohexahydronaphth[2,3-e][1,2]oxazines. 2." Acta Crystallographica Section C Crystal Structure Communications 43, no. 3 (1987): 598–601. http://dx.doi.org/10.1107/s0108270187094861.

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20

Kukharev, B. F., V. K. Stankevich, G. R. Klimenko, V. V. Bayandin, and V. A. Kukhareva. "Reaction of perhydro-1,3-oxazines with 2-sulfanylacetic acid." Russian Journal of Organic Chemistry 42, no. 7 (2006): 1101–2. http://dx.doi.org/10.1134/s1070428006070359.

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21

Tolchinskii, S. E., M. V. Kormer, and I. A. Maretina. "Synthesis of 2-substituted naphth[1,8-de]-1,3-oxazines." Chemistry of Heterocyclic Compounds 27, no. 4 (1991): 424–25. http://dx.doi.org/10.1007/bf00480843.

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22

Kurlykin, M. P., M. M. Dudkina, and A. V. Ten’kovtsev. "Star-Shaped Thermosensitive Poly(2-ethyl-2-oxazines) with the Calixarene Core." Polymer Science, Series B 61, no. 1 (2019): 51–55. http://dx.doi.org/10.1134/s156009041806009x.

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23

Thirunarayanan, Ganesamoorthy, R. Sundararajan, and R. Arulkumaran. "Aryl Chalcones as Efficient Precursors for Deriving Oxazine: Solvent-Free Synthesis and Antimicrobial Activities of some Oxazine-2-amines." International Letters of Chemistry, Physics and Astronomy 23 (November 2013): 82–97. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.23.82.

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A series of some oxazine derivatives has been synthesised by fly-ash:H2SO4 catalyzed solvent-free cyclization of aryl chalcones and urea under microwave irradiation. The yields of the oxazines were more than 85%. The synthesised oxazines were characterized by their physical constants, analytical and spectroscopic data. The antimicrobial activities of these oxazines have been studied using Bauer-Kirby method.

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24

Nabeya, Aiko, Tadatoshi Endo, Jun Saito, Takatoshi Mitsuishi, and Masashi Inahara. "Reaction of isocyanates with 2-phenyliminotetrahydro-1,3-thiazines and oxazines." Journal of Heterocyclic Chemistry 27, no. 4 (1990): 903–7. http://dx.doi.org/10.1002/jhet.5570270416.

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25

Belasri, Khadija, Leila Topal, Matthias Heydenreich, et al. "Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives." Molecules 25, no. 11 (2020): 2524. http://dx.doi.org/10.3390/molecules25112524.

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The synthesis of new phenanthr[9,10-e][1,3]oxazines was achieved by the direct coupling of 9-phenanthrol with cyclic imines in the modified aza-Friedel–Crafts reaction followed by the ring closure of the resulting bifunctional aminophenanthrols with formaldehyde. Aminophenanthrol-type Mannich bases were synthesised and transformed to phenanthr[9,10-e][1,3]oxazines via [4 + 2] cycloaddition. Detailed NMR structural analyses of the new polyheterocycles as well as conformational studies including Density Functional Theory (DFT) modelling were performed. The relative stability of ortho-quinone met

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26

Wanapun, D., K. A. Van Gorp, N. J. Mosey, M. A. Kerr, and T. K. Woo. "The mechanism of 1,3-dipolar cycloaddition reactions of cyclopropanes and nitrones A theoretical study." Canadian Journal of Chemistry 83, no. 10 (2005): 1752–67. http://dx.doi.org/10.1139/v05-182.

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The 1,3-dipolar cycloaddition reaction of cyclopropanes and nitrones to give tetrahydro-1,2-oxazine has been studied with density functional theory calculations at the B3LYP/6-31+G(d,p) level of theory. Realistic substituents were modelled including those at the 2-, 3-, 4-, and 6-positions of the final oxazine ring product. The strained σ bond of the cyclopropane was found to play the role of an alkene in a conventional [3+2] dipolar cycloaddition. Two distinct, but similar, reaction mechanisms were found an asymmetric concerted pathway and a stepwise zwitterionic pathway. The reaction barri

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27

Natarajan, Palani, Priya, and Deachen Chuskit. "Persulfate-activated charcoal mixture: an efficient oxidant for the synthesis of sulfonated benzo[d][1,3]oxazines from N-(2-vinylphenyl)amides and thiols in aqueous solution." RSC Advances 11, no. 26 (2021): 15573–80. http://dx.doi.org/10.1039/d1ra02377b.

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A simple method for the synthesis of 2,4-aryl-4-((arylsulfonyl)methyl)-4H-benzo[d][1,3]oxazines using an easily accessible K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-activated charcoal mixture and thiols, respectively, as an oxidant and sulfonylating precursors has been described.

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28

Scholz, S., and B. Plietker. "Fe-Catalyzed reductive NO-bond cleavage – a route to the diastereoselective 1,4-aminohydroxylation of 1,3-dienes." Organic Chemistry Frontiers 3, no. 10 (2016): 1295–98. http://dx.doi.org/10.1039/c6qo00255b.

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We describe the iron-catalyzed reductive cleavage of N–O-bonds in oxazines using malononitrile as reductant, which – in sequence with a [4 + 2]-cycloaddition – can be considered as an efficient way for the diastereoselective 1,4-aminohydroxylation of 1,3-dienes.

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29

Korepin, A. G., P. V. Galkin, E. K. Perepelkina, N. M. Glushakova, I. L. Eremenko та L. T. Eremenko. "N-substituted tetrahydro-1,3-oxazines and -oxazolidines. 2. Nitration of N-(ω-acylamino-β,β-dinitroalkyl)tetrahydro-1,3-oxazines and -oxazolidines". Russian Chemical Bulletin 58, № 10 (2009): 2103–8. http://dx.doi.org/10.1007/s11172-009-0287-9.

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30

Fülöp, Ferenc, György Csirinyi, Gábor Bernáth, and József A. Szabó. "An Efficient Method for the Preparation of 2-Thioxotetrahydro-1,3-oxazines." Synthesis 1985, no. 12 (1985): 1149–51. http://dx.doi.org/10.1055/s-1985-31458.

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31

Cwik, Agnieszka, Zoltan Hell, Adrienn Hegedues, Zoltan Finta, and Zoltan Horvath. "ChemInform Abstract: A Simple Synthesis of 2-Substituted Oxazolines and Oxazines." ChemInform 33, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.200237131.

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TOLCHINSKII, S. E., M. V. KORMER, and I. A. MARETINA. "ChemInform Abstract: Synthesis of 2-Substituted Naphth(1,8-de)-1,3-oxazines." ChemInform 23, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199238182.

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33

Rostovskii, Nikolai V., Mikhail S. Novikov, Alexander F. Khlebnikov, Galina L. Starova та Margarita S. Avdontseva. "Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization". Beilstein Journal of Organic Chemistry 11 (2 березня 2015): 302–12. http://dx.doi.org/10.3762/bjoc.11.35.

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Strained azirinium ylides derived from 2H-azirines and α-diazoketones under Rh(II)-catalysis can undergo either irreversible ring opening across the N–C2 bond to 2-azabuta-1,3-dienes that further cyclize to 2H-1,4-oxazines or reversibly undergo a 1,5-cyclization to dihydroazireno[2,1-b]oxazoles. Dihydroazireno[2,1-b]oxazoles derived from 3-aryl-2H-azirines and 3-diazoacetylacetone or ethyl diazoacetoacetate are able to cycloadd to acetyl(methyl)ketene generated from 3-diazoacetylacetone under Rh(II) catalysis to give 4,6-dioxa-1-azabicyclo[3.2.1]oct-2-ene and/or 5,7-dioxa-1-azabicyclo[4.3.1]de

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34

Prep'yalov, A. V., I. P. Yakovlev, and V. E. Zakhs. "Reactions of Unsaturated 1,3-Oxazines; I. Reaction of 6-Alkoxy-2-aryl-4H-1,3-oxazine-4-one with Hydrazine Derivatives." Synthesis 1999, no. 03 (1999): 483–86. http://dx.doi.org/10.1055/s-1999-3409.

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35

Deniz, Erhan, Stefania Impellizzeri, Salvatore Sortino, and Françisco M. Raymo. "A photoswitchable bichromophoric oxazine with fast switching speeds and excellent fatigue resistance." Canadian Journal of Chemistry 89, no. 2 (2011): 110–16. http://dx.doi.org/10.1139/v10-070.

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In search of strategies to regulate the photochemical and photophysical properties of photochromic oxazines, we designed a multichromophoric compound incorporating 3H-indole, benzooxazine, and 2-(4-dimethylaminophenyl)ethynyl fragments. We synthesized this molecule in two steps in an overall yield of 51%, starting from commercial precursors. The ultraviolet irradiation of this photochrome opens a [1,3]oxazine ring in less than 6 ns to generate a zwitterionic isomer with a quantum yield of 0.10. In particular, the photoinduced ring opening generates a 4-nitrophenolate anion and a 3H-indolium ca

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36

Burger, Klaus, Norbert Sewald, Erasmus Huber, and Ralph Ottlinger. "Reaktionen 4,4-Bis(trifluormethyl)-substituierter Heterodiene mit Alkinen / Reactions of 4,4-Bis(trifluoromethyl) Substituted Heterodienes with Alkynes." Zeitschrift für Naturforschung B 44, no. 10 (1989): 1298–312. http://dx.doi.org/10.1515/znb-1989-1026.

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4,4-Bis(trifluoromethyl) substituted 1-oxa-3-azabuta-1,3-dienes (1) and alkynes react to give open-chain trifluoromethyl substituted N-propargylic amides (4), 4H-1,3-oxazines (5) and 2-oxazolines (6, 7), respectively. The selectivity of the reaction can be controlled effectively by the reaction conditions used.

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37

Szakonyi, Zsolt, Istvan Zupko, and Ferenc Fulop. "Stereoselective Synthesis and Antiproliferative Activity of Monoterpene-Fused 2- Imino-1,3-oxazines." Current Organic Synthesis 14, no. 4 (2017): 612–19. http://dx.doi.org/10.2174/1570179414666161116110813.

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38

Vainiotalo, Pirjo, Ferenc Fülöp, GÁBor Bernáth, and Kalevi Pihlaja. "Mass spectrometric intramolecular cyclization reactions of some 2-N-phenyliminoperhydro-1,3-oxazines." Journal of Heterocyclic Chemistry 26, no. 5 (1989): 1453–59. http://dx.doi.org/10.1002/jhet.5570260540.

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39

Sheradsky, Tuvia, and Elliad R. Silcoff. "The reaction of phenylglyoxal with 2-aminoalcohols. Rearrangement of 2-acyloxazolidines to 2-hydroxy-5,6-dihydro-1,4-oxazines." Journal of Heterocyclic Chemistry 33, no. 4 (1996): 1271–74. http://dx.doi.org/10.1002/jhet.5570330445.

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40

TINANT, B., and J. P. DECLERCQ. "ChemInform Abstract: Structures of N-Substituted 1,2-Oxazines. Part 2. Bicyclic Bridged Derivatives." ChemInform 22, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199138056.

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41

Tishkov, Alexander A., Alexey V. Lesiv, Yulya A. Khomutova, et al. "2-Silyloxy-1,2-oxazines, a New Type of Acetals of Conjugated Nitroso Alkenes." Journal of Organic Chemistry 68, no. 24 (2003): 9477–80. http://dx.doi.org/10.1021/jo034669a.

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42

Tabolin, Andrey A., Alexey V. Lesiv, Yulia A. Khomutova, Yulia V. Nelyubina та Sema L. Ioffe. "Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines". Tetrahedron 65, № 23 (2009): 4578–92. http://dx.doi.org/10.1016/j.tet.2009.03.082.

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43

Lai, Ellen C. K., Donald Mackay, Nicholas J. Taylor, and Kenneth N. Watson. "Competitive [4 + 2] and [3 + 2] cycloadditions of nitrosoalkenes to the imino bond of bicyclic 1,2-oxazines." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1990): 1497. http://dx.doi.org/10.1039/p19900001497.

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44

Pongó, László, Péter Dvortsák, and József Reiter. "The Reaction of Dimethyl N-(1,2,4-Triazol-5-yl)iminodithiocarbonates with Dinucleophiles." Collection of Czechoslovak Chemical Communications 57, no. 1 (1992): 134–52. http://dx.doi.org/10.1135/cccc19920134.

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Abstract:

A series of N-(3-methylthio-1,2,4-triazol-5-yl) substituted carbamimidothioates (III), 2-iminoazolidines (IV, X = O, S, NH, n = 2), 2-iminohexahydro-1,3-oxazines (IV, X = O, n = 3), 2-iminohexahydropyrimidines (IV, X = NH, n = 3), and N,N'-alkylenebis(carbamimidothioates) (V) was prepared from dimethyl N-(3-methylthio-1,2,4-triazol-5-yl)iminodithiocarbonates (I). N-substituted azolidines IV, X = O, S, NH, n = 2, such as acetyl, methyl, (ethoxycarbonyl)methyl, 1-(ethoxycarbonyl)ethyl, 2-chloroethylcarbamoyl, 2-cyano-2-(ethoxycarbonyl)ethenyl, and 2,2-dicyanoethenyl, were also prepared. The stru

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45

Prep'yalov, A. V., I. P. Yakovlev, and V. E. Zakhs. "ChemInform Abstract: Reactions of Unsaturated 1,3-Oxazines. Part 1. Reaction of 6-Alkoxy-2-aryl-4H-1,3-oxazine-4-one with Hydrazine Derivatives." ChemInform 30, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199927174.

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46

Holzapfel, C. W., G. J. Kruger, and M. S. Dyk. "Structures of 3-cyanohexahydronaphth-[2,3-e]-1,2-oxazines part 3: Comparison of the conformations of some 3-cyanotetrahydro-1, 2-oxazine ring systems." Journal of Crystallographic and Spectroscopic Research 17, no. 4 (1987): 515–32. http://dx.doi.org/10.1007/bf01180324.

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47

Shahrisa, Aziz, Reza Teimuri-Mofrad, and Mahdi Gholamhosseini-Nazari. "Chemoselective Sequential Reactions for the Synthesis of 12H-Benzo[a]xanthenes and Dihydro-1H-naphtho[1,2-e][1,3]oxazines." Synlett 26, no. 08 (2015): 1031–38. http://dx.doi.org/10.1055/s-0034-1380323.

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Abstract:

Novel sequential Betti–Ullmann and Betti–C–H activation reactions for the synthesis of 12H-benzo[a]xanthenes and dihydro-1H-naphtho[1,2-e][1,3]oxazines have been developed. Depending on the used conditions selective Ullmann-type arylation or α-C-H aryloxylation of 2-bromophenyl alkylaminonaphthols occurred. A simple, fast, green, and high-yielding method for the synthesis of aminonaphthols catalyzed by bismuth(III) chloride under solvent-free conditions is reported.

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48

SHERADSKY, T., and E. R. SILCOFF. "ChemInform Abstract: The Reaction of Phenylglyoxal with 2-Aminoalcohols. Rearrangement of 2- Acyloxazolidines to 2-Hydroxy-5,6-dihydro-1,4-oxazines." ChemInform 28, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199701205.

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49

Glover, SA, GP Hammond, DG Harman, JG Mills, and CA Rowbottom. "Cyclization of Alkoxyiminyl Radicals Onto Olefins: Formation of 2-Alkoxy-Delta(1)-Pyrrolines, 4,5-Dihydrooxazoles and 5,6-Dihydrol-4h-1,3-Oxazines." Australian Journal of Chemistry 46, no. 8 (1993): 1213. http://dx.doi.org/10.1071/ch9931213.

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Abstract:

Alkoxyiminyl radicals, generated by photolysis of N-bromo imidates, undergo exo-1,5 and exo-1,6 cyclization onto olefins on the O-alkyl side chains giving good yields of 4,5-dihydrooxazoles and 5,6-dihydro-4H-1,3-oxazines, respectively. exo-1,5 Cyclization onto an olefin on the iminyl side chain gives 2-alkoxy-Δ1-pyrrolines. 4,5-Dihydrooxazole formation is more favourable than cyclization to 2-alkoxy-Δ1-pyrrolines and both reactions are irreversible. These preferences are supported by MNDO molecular orbital calculations which predict that both processes are exothermic but cyclization onto the

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50

Kurihara, Takushi, Tatsuya Terada, Yoshitaka Matsubara, and Ryuji Yoneda. "A New Synthetic Method of 6-Aryl- or Vinyl-substituted 2-Oxotetrahydro-1,3-oxazines." HETEROCYCLES 26, no. 3 (1987): 641. http://dx.doi.org/10.3987/r-1987-03-0641.

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