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Journal articles on the topic '2-oxazine'

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Published: 4 June 2021

Last updated: 9 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 (April 29, 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-2-alkyl-2-oxazolines. On heating below the phase separation temperature, the characteristics of the investigated solutions did not depend practically on temperature. An increase in the dehydration degree of poly-2-alkyl-2-oxazines and poly-2-alkyl-2-oxazolines led to the formation of intermolecular hydrogen bonds, and aggregation was the dominant process near the phase separation temperature. It was shown that the characteristics of the phase transition in solutions of the studied polymer stars are determined primarily by the arm structure, while the influence of the molar mass is not so significant. In comparison with literature data, the role of the hydrophobic core structure in the formation of the properties of star-shaped polymers was analyzed.

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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 (November 12, 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 concerted efforts expended on most of the synthetic routes to the various types of pyrazolo-oxazines in the literature until the first quarter of 2020. The reactions of pyrazolo-oxazines with various reagents are also outlined.

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4

Lauro, Figueroa-Valverde, Díaz-Cedillo Francisco, Rosas-Nexticapa Marcela, García-Cervera Elodia, Pool-Gómez Eduardo, López-Ramos María, Hau-Heredia Lenin, and Sarabia-Alcocer Betty. "Design and Synthesis of Two Oxazine Derivatives Using Several Strategies." Journal of Chemistry 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/757953.

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Several oxazine derivatives have been synthesized; nevertheless, expensive reagents and special conditions are required. Therefore, in this study, two oxazine derivatives (2-chloro-3-{{2-[-(3-chloro-2-oxo-cyclobutyl)-(2,3-dimethoxy-9,10-dihydrostrychnid-10-yl)-amino]-ethyl}-[1,5-dimethyl-4-(1H-naphtho[1,2-e][1,3-oxazin-2-yl)-2-phenyl-2,3-dihydro-1H-pyrazol-3-yl]-amino}-cyclobutanone and 2-chloro-3-{{2-[(3-chloro-2-oxo-cyclobutyl)-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amino]-ethyl}-[1,5-dimethyl-4-(1H-naphtho[1,2-e][1,3]oxazin-2-yl)-2-phenyl-2,3-dihydro-1H-pyrazol-3-yl]-amino}-cyclobutanone) were synthesized using several strategies. The structure of compounds obtained was confirmed by elemental analysis, spectroscopy, and spectrometry data. In conclusion, the methods used offer some advantages such as good yields, simple procedure, low cost, and ease of workup.

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5

Farfán, Norberto, Rosa L. Santillan, Dolores Castillo, Reyna Cruz, Pedro Joseph-Nathan, and Jean-Claude Daran. "Fused heterocycles derived from pseudoephedrine and ephedrine." Canadian Journal of Chemistry 70, no. 11 (November 1, 1992): 2764–70. http://dx.doi.org/10.1139/v92-351.

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The formation of heterobicycles by condensation of (1R, 2R)-(−)-pseudoephedrine or (1R, 2S)-(−)-ephedrine with glyoxal is reported. In the case of pseudoephedrine, the nuclear magnetic resonance data of the crude reaction mixture indicate the presence of three isomeric compounds (5, 6, and 7), which were separated by fractional crystallization, while ephedrine afforded the oxazino-oxazine 8 and the known (5S*,6R*)-4,5-dimethyl-6-phenyl-1,4-oxazin-2-one (9). Conclusive spectroscopic evidence for the structures of the new compounds having the cis-[1,4]oxazino[3,2-b]-1,4-oxazine (5 and 8) and the 2,2′-bioxazolidine type structures (6 and 7) was obtained by measurement of the 13C satellite coupling constants in the 300 MHz 1H nmr spectra, combined with the evaluation of dihedral angles using a modified Karplus type relationship. Unequivocal 1H and 13C nmr spectral assignments for all new compounds were done using two-dimensional carbon–proton correlation experiments. Syntheses of the known 5a,6,11a,12-tetrahydro[1,4]benzoxazino[3,2-b]benzoxazine (3a) whose crystal structure has been previously determined, as well as of its N,N′-diisopropyl derivative 3b, allowed us to corroborate the above observations for the six-membered ring heterocycles. Moreover, the structures of 3b and 7 were independently verified by single crystal X-ray diffraction studies, thus validating the structural conclusions deduced from nmr satellite multiplicity measurements.

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6

Konstantinova, Lidia S., Mikhail A. Tolmachev, Vadim V. Popov, and Oleg A. Rakitin. "Ethyl 11a,12-Dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate." Molbank 2020, no. 3 (July 21, 2020): M1149. http://dx.doi.org/10.3390/m1149.

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The 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine heterocyclic system has been used in the construction of heteropropellanes, which attracted much attention not only on the possible modification of drugs, but also for novel materials with unusual and important physical properties. In this communication, the reaction of ethyl 2-(hydroxyimino)propanoate 1 with disulfur dichloride and o-aminophenol, which gave ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate in moderate yield, was described. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy, mass-spectrometry and X-ray analysis.

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7

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 (April 4, 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 depends on the structure of the salt and polymer and on the salt content in the solution. The phase separation temperature decreased with an increase in the hydrophobicity of the polymers, which is caused by both a growth of the side radical size and an elongation of the monomer unit. For NaCl solutions, the phase separation temperature monotonically decreased with growth of salt concentration. In solutions with methylpyridinium p-toluenesulfonate, the dependence of the phase separation temperature on the salt concentration was non-monotonic with minimum at salt concentration corresponding to one salt molecule per one arm of a polymer star. Poly-2-alkyl-2-oxazine and poly-2-alkyl-2-oxazoline stars with a hexaaza[26]orthoparacyclophane core are more sensitive to the presence of salt in solution than the similar stars with a calix[n]arene branching center.

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8

Chovatiya, Pankaj, Charmy Mehta, Hardik Senjani, Anamik Shah, and Hitendra S. Joshi. "Synthesis and Characterization of some New Schiff Bases of 2-Oxonaphtho[2,1-b][1,4]Oxazine." International Letters of Chemistry, Physics and Astronomy 31 (March 2014): 26–30. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.31.26.

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The literature review reveal that [1,4]-oxazine derivatives represent one of the most active classes of compounds possessing wide spectrum of biodynamic activities and use as potent therapeutic agents. In the present work, a series of Schiff base of 2-(2,3-dihydro-2-oxonaphtho[2,1-b][1,4]oxazin-1-yl)acetohydrazide, 5a-5j has been synthesized using 1-aminonaphthalen-2-ol. Various aromatic aldehyde were react with carbohydrazide 4 in the presence of acid to produce the 2-oxonaphtho[2,1-b][1,4]oxazin Schiff base derivatives with good yields. All synthesized compounds were characterized by IR, NMR and Mass spectrometry analysis.

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9

Bloksma, Meta M., Renzo M. Paulus, Huub P. C. van Kuringen, Friso van der Woerdt, Hanneke M. L. Lambermont-Thijs, Ulrich S. Schubert, and Richard Hoogenboom. "Thermoresponsive Poly(2-oxazine)s." Macromolecular Rapid Communications 33, no. 1 (November 25, 2011): 92–96. http://dx.doi.org/10.1002/marc.201100587.

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10

Pathan, Mosim, and Faiz Khan. "Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction." SynOpen 02, no. 02 (April 2018): 0150–60. http://dx.doi.org/10.1055/s-0036-1591960.

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Pyrido-oxazine derivatives have been synthesized by employing tandem SN2 and SNAr reaction between 2,4,6-tribromo-3-(2-bromoethoxy)pyridine or 2,4,6-tribromo-3-(3-bromopropoxy)pyridine and a variety of primary amines. Moderate to good regioselectivity in favor of cyclization at the 2-position is observed. Pyrido-oxazine products thus generated are converted into biarylated pyrido-oxazine and terpyridine ligands.

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11

Cui, Shaoying, Carlos R. Arza, Pablo Froimowicz, and Hatsuo Ishida. "Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening." Polymers 12, no. 3 (March 20, 2020): 694. http://dx.doi.org/10.3390/polym12030694.

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In this study, 2-(aminomethyl)phenol and its derivatives, the reactants for 2-substituted 1,3-benzoxazines, are synthesized by HCl hydrolysis from the typical benzoxazines. The phenol/aniline-based mono-oxazine benzoxazine, PH-a, and the bisphenol A/aniline-based bis-oxazine benzoxazine, BA-a, are used as examples to demonstrate the feasibility of this new approach. Their chemical structures are characterized by nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman spectroscopies, and are further verified by elementary analysis. Their thermal properties are studied by differential scanning calorimetry (DSC). These two 2-(aminomethyl) phenolic derivatives are reacted with paraformaldehyde to close the oxazine rings. A benzoxazine with a phenyl substituent at the 2-position of the oxazine ring is obtained from the 2-((phenylamino)methyl)phenol (hPH-a) and benzaldehyde. All these results highlight the success of the HCl hydrolysis and the formation of stable intermediates, namely 2-(aminomethyl) phenolic derivatives, from readily available benzoxazine monomers. This further demonstrates the feasibility of using these intermediates as reactants for a novel benzoxazine synthesis.

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12

Ravikumar, Krishnan, Balasubramanian Sridhar, Jagadeesh Babu Nanubolu, Venkatasubramanian Hariharakrishnan, and Awadesh Narain Singh. "Structures of benzoxazine-fused triazoles as potential diuretic agents." Acta Crystallographica Section C Crystal Structure Communications 68, no. 8 (July 13, 2012): o302—o307. http://dx.doi.org/10.1107/s0108270112029800.

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6,8-Dinitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one, C9H5N5O6, (I), a potential diuretic, and its acetylacetone derivative (E)-2-(2-hydroxy-4-oxopent-2-en-3-yl)-6,8-dinitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one, C14H11N5O8, (II), both crystallize from methanol but in centrosymmetric and noncentrosymmetric space groups, respectively. To the best of our knowledge, this is the first report of crystal structures of benzoxazine–triazole fused systems. The acetylacetone group in (II) exists as the keto–enol tautomer and is oriented perpendicular to the triazol-3-one ring. Of the two nitro groups present, one is rotated significantly less than the other in both structures. The oxazine ring adopts a screw-boat conformation in (II), whereas it is almost planar in (I). N—H...N and N—H...O hydrogen bonds form centrosymmetric dimers in (I), while C—H...O interactions associate the molecules into helical columns in (II).

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13

Couture, Philippe, and John Warkentin. "Spiro-fused 2-alkoxy-2-amino-Δ3-1,3,4-oxadiazolines. Synthesis and thermolysis to corresponding aminooxycarbenes." Canadian Journal of Chemistry 75, no. 9 (September 1, 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,e) afford essentially quantitative yields of the corresponding aminooxycarbenes, while other fragmentation reactions compete with carbene generation in the case of oxadiazolines with N-methyl (12b, 13c) or N-sulfonyl (12k) groups. Keywords: nucleophilic carbene, aminooxycarbene, oxadiazoline, oxazolidin-2-ylidene, carbonyl ylide.

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14

Pospelov, Evgeny V., Ivan S. Golovanov, Sema L. Ioffe, and Alexey Yu Sukhorukov. "The Cyclic Nitronate Route to Pharmaceutical Molecules: Synthesis of GSK’s Potent PDE4 Inhibitor as a Case Study." Molecules 25, no. 16 (August 8, 2020): 3613. http://dx.doi.org/10.3390/molecules25163613.

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An efficient asymmetric synthesis of GlaxoSmithKline’s potent PDE4 inhibitor was accomplished in eight steps from a catechol-derived nitroalkene. The key intermediate (3-acyloxymethyl-substituted 1,2-oxazine) was prepared in a straightforward manner by tandem acylation/(3,3)-sigmatropic rearrangement of the corresponding 1,2-oxazine-N-oxide. The latter was assembled by a (4 + 2)-cycloaddition between the suitably substituted nitroalkene and vinyl ether. Facile acetal epimerization at the C-6 position in 1,2-oxazine ring was observed in the course of reduction with NaBH3CN in AcOH. Density functional theory (DFT) calculations suggest that the epimerization may proceed through an unusual tricyclic oxazolo(1,2)oxazinium cation formed via double anchimeric assistance from a distant acyloxy group and the nitrogen atom of the 1,2-oxazine ring.

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15

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 (April 3, 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 rigidity of arms. The star-shaped polypeptoids have relatively high intramolecular density. All synthesized stars exhibit LCST behavior. Phase separation temperature depends on arm structure. It is lower for poly-2-alkyl-2-oxazines, monomer units of which contains one methylene group more than monomers of poly-2-alkyl-2-oxazoline.

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16

Stasevych, Maryna, Svitlana Sabat, Rostyslav Musyanovych, and Volodymyr Novikov. "Synthesis of condensed S-, N- containing heterocyclic systems on the base of 2-amino-4,9-dioxo-4,9-dihydronaphto[2,3-b]thiophene-3-ethylcarboxilate." Chemistry & Chemical Technology 2, no. 3 (September 15, 2008): 157–62. http://dx.doi.org/10.23939/chcht02.03.157.

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Synthesis of a new 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones, 2-arylnaphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-4,5,10(3Н)-triones, 3-phenyl naphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-2,4,5,10(1Н, 3Н)-tetraone and 2-thioxo-2,3-dyhydronaphth[2’,3’,4,5]thieno[2,3-d]pyrimidine-4,5,10(1Н)-trione was carried out. The mechanism of 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones formation was suggested.

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17

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 (October 1, 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 barriers of the two pathways were nearly identical, differing by less than ~1 kcal/mol, no matter what the substituents were. The effect of a Lewis acid catalyst was examined and found to have a very large effect on the calculated barriers through coordination to the carbonyl oxygen atoms of the diester substituents on the cyclopropane. The reaction barrier was found to decrease by as much as ~19 kcal/mol when using a BF3 molecule as a model for the Lewis acid catalyst. Solvent effects and the nature of the regiospecificity of the reaction were also examined. Trends in the calculated barriers for the reaction were in good agreement with available trends in the reaction rates measured experimentally. Key words: 1,3-dipolar cycloaddition, cyclopropane, nitrone, tetrahydro-1,2-oxazines, ab initio quantum chemistry, mechanism.

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18

Ochędzan-Siodłak, Wioletta, Dawid Siodłak, Aleksandra Piontek, and Karel Doležal. "Titanium and Vanadium Catalysts with 2-Hydroxyphenyloxazoline and Oxazine Ligands for Ethylene-Norbornene (co)Polymerization." Catalysts 9, no. 12 (December 8, 2019): 1041. http://dx.doi.org/10.3390/catal9121041.

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A series of titanium and vanadium complexes with oxazoline 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol (L1), 2-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenol (L2), and oxazine 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol (L3) ligands were synthesized, and their structures were determined by NMR and MS methods as (L)2MtCl2. The vanadium complexes were found to be highly active in ethylene (7300 kgPE/(molV·h)) and ethylene/norbornene (5300 kgCop/(molV·h)) (co)polymerization. The polyethylene characteristics were melting temperature (123–142 °C), crystallinity degree (49–75%), molecular weight (5.7–8.5 × 105 g/mol), molecular weight distribution (1.5–2.4). The ethylene-norbornene (E-NB) copolymer characteristics were molecular weight (2.6–0.9 × 105 g/mol), molecular weight distribution (1.6–2.2), glass transition temperature (4–62 °C), norbornene incorporation (12.3–30.1 mol%) at initial concentration (0.5–1.5 mol/L). The microstructure of E-NB copolymers depends on the catalyst applied with the highest diads content for the (L3)2VCl2 and triads for the (L2)2VCl2 complexes.

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19

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 (February 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 gold intermediate to generate a carbocation intermediate which is trapped by the nucleophilic oxygen of the nitrone to form a furanyl–gold complex, which upon subsequent cyclization affords the furo [3,4-d] [1,2] oxazine as well as regenerates the gold catalyst. The highest activation barrier in the entire cycle is 19.5[Formula: see text]kcal/mol which accompanies the intramolecular cyclization step. The activation barriers for the reactions of 2-(1-alkynyl)2-alken-1-ones with electron-donating and cyclic substituents are generally lower compared to those of the parent 2-(1-alkynyl)2-alken-1-one while the reactions of 2-(1-alkynyl)2-alken-1-ones with electron-withdrawing substituents have higher activation barriers. Preliminary exploratory calculations on the possibility of replacing gold, an expensive and rare metal, with a copper-based catalyst for the reaction, show that for the key elementary steps, the Cu (III) catalyst is at least as active as the Au (III) complex, thus providing a cheaper route to furo [3,4-d] [1,2] oxazine.

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20

Görlach, Ekkehard, Hansruedi Gygax, Paolo Lubini, and Urs P. Wild. "Solvent relaxation of oxazine-4 in 2-methyltetrahydrofuran." Chemical Physics 194, no. 1 (May 1995): 185–93. http://dx.doi.org/10.1016/0301-0104(95)00002-6.

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21

Ghaffari-Nia, Nooshin, and Alireza Hassanabadi. "Three-Component One-Pot Condensation of 2-Hydroxy-1,4-Naphthoquinone with Aromatic Aldehydes and Methyl Carbamate: Synthesis of 4-aryl-3,4-Dihydronaphtho[3,4-e][1,3]Oxazine-2,5,10-Trione in Aqueous Media." Journal of Chemical Research 42, no. 6 (June 2018): 291–93. http://dx.doi.org/10.3184/174751918x15287173761289.

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A green and efficient method for oxazine ring formation is established using the reaction of 2-hydroxy-1,4-naphthoquinone and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydronaphtho[3,4- e][1,3] oxazine-2,5,10-triones in excellent yields. The salient features of this protocol are short reaction times and high yields while avoiding any hazardous organic solvent. Therefore, this procedure could be classified as green chemistry.

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22

Abdollahi–Irandegan, Allahbakhsh, and Alireza Hassanabadi. "Synthesis of 4-aryl-7-methyl-3,4-dihydropyrano[3,4-e][1,3]oxazine-2,5-dione in Aqueous Media." Journal of Chemical Research 40, no. 12 (December 2016): 727–28. http://dx.doi.org/10.3184/174751916x14787187457361.

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A novel method for oxazine ring formation is established using the reaction of 4-hydroxy-6-methyl-2H-pyran-2-one and aromatic aldehydes with methyl carbamate in the presence of p-toluene sulfonic acid (p-TSA) in aqueous media to afford 4-aryl-7-methyl-3,4-dihydropyrano[3,4-e][1,3]oxazine-2,5-dione in excellent yields. The present method does not involve any hazardous organic solvents and could therefore be considered a green process.

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23

Ohashi, Seishi, Francis Cassidy, Stephanie Huang, Kevin Chiou, and Hatsuo Ishida. "Synthesis and ring-opening polymerization of 2-substituted 1,3-benzoxazine: the first observation of the polymerization of oxazine ring-substituted benzoxazines." Polymer Chemistry 7, no. 46 (2016): 7177–84. http://dx.doi.org/10.1039/c6py01686c.

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24

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 (December 1, 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 plots of log km/kH vs. Hammett σ+ values give straight lines with the ρ values lying between −0.60 and −0.91 for the reactions with 2-aryl-1,3-butadienes. A concerted reaction mechanism is proposed and the orientation preference is consistent with frontier molecular orbital predictions for 2-alkyl-1,3-butadienes. In the reactions with 2-aryl-1,3-butadienes, a transition state leading to a spin-paired diradical, which then converts by partial electron transfer to zwitterionic structure, is proposed. Keywords: trichloronitrosomethane, 3,6-dihydro-1,2-oxazine, regioselectivity, [2 + 4] cycloaddition.

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25

Sharma, S. D., Paloth Venugopalan, and Susmita Bhaduri. "Synthesis and X-ray Crystallographic Analysis of 4,4′-Disubstituted N–(2-Hydroxypropyl)Azetidin-2-One from Benzil and (±)-2-Amino-1-Methylethanol." Journal of Chemical Research 2003, no. 3 (March 2003): 170–71. http://dx.doi.org/10.3184/030823403103173372.

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5,6-Dihydro-2-hydroxy-6-methyl-2,3-diphenyl-2 H-1,4-oxazine 1, derived from benzil and (±)-2-amino-1-methylethanol, reacts with phenoxyacetyl chloride in the presence of triethylamine to give a single isomer of a 4,4′-disubstituted azetidin-2-one 2, whose structure has been unambiguously confirmed by X-ray crystallographic analysis.

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26

Rivera, Augusto, Jicli José Rojas, Jaime Ríos-Motta, and Michael Bolte. "Crystal structure of 1-[(2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-2-yl)methyl]naphthalen-2-ol: a possible candidate for new polynaphthoxazine materials." Acta Crystallographica Section E Crystallographic Communications 71, no. 9 (August 26, 2015): 1089–92. http://dx.doi.org/10.1107/s2056989015015583.

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In the title compound, C23H19NO2, an oxazine Mannich base derivative, the oxazine ring has a half-chair conformation. The 2-hydroxynaphthalen-1-yl substituent is placed in an axial position. There is an intramolecular O—H...N hydrogen bond, forming anS(6) graph-set motif. In the crystal, molecules are connected by a pair of C—H...π interactions into an inversion dimer, which is reinforced by another pair of weak C—H...π interactions. The dimers are linked by a π–π interaction [centroid-centroid distance = 3.6268 (17) Å], consolidating a column along theaaxis. Furthermore, the columns interact with each other by a weak C—H...π interaction, generating a three-dimensional network.

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27

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 (February 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 cation. Additionally, this process brings the 2-(4-dimethylaminophenyl)ethynyl appendage into conjugation with the 3H-indolium cation. As a result, two distinct bands for the anionic and cationic fragments of the photogenerated zwitterion appear in the visible region of the absorption spectrum. The photogenerated isomer has a lifetime of 2 µs and switches back to the original form with first-order kinetics. Furthermore, this bichromophoric photochrome tolerates hundreds of switching cycles with no sign of degradation and can be operated within rigid polymer matrices. Thus, this particular structural design can lead to the development of a new family of bichromophoric photochromes and photoresponsive materials with microsecond switching times and excellent fatigue resistances.

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28

Shoja, M., and S. Saba. "3-Isopropyl-2-(4-nitrophenyl)-2,3,4,5-tetrahydro-1,3-oxazine." Acta Crystallographica Section C Crystal Structure Communications 47, no. 9 (September 15, 1991): 1994–96. http://dx.doi.org/10.1107/s0108270191001658.

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29

Rivera, Augusto, Juan E. Cepeda-Santamaría, Jaime Ríos-Motta, and Michael Bolte. "Crystal structure of 2,2′-(ethane-1,2-diyl)bis(2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine): a prospective raw material for polybenzoxazines." Acta Crystallographica Section E Crystallographic Communications 73, no. 6 (May 9, 2017): 832–34. http://dx.doi.org/10.1107/s2056989017006673.

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In the title compound, C26H24N2O2, the oxazine moiety is fused to a naphthalene ring system. The asymmetric unit consists of one half of the molecule, which lies about an inversion centre. The C atoms of the ethylene spacer group adopt an antiperiplanar arrangement. The oxazine ring adopts a half-chair conformation. In the crystal, supramolecular chains running along thebaxis are formedviashort C—H...π contacts. The crystal studied was a non-merohedral twin with a fractional contribution of 0.168 (2) of the minor twin component.

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30

Zhou, Hui, Rui Wang, Hui Zhang, Wei Chen, and Xiao-Bing Lu. "Access to 1,3-oxazine-2,4-diones/1,3-thiazine-2,4-diones via organocatalytic CO2/COS incorporation into allenamides." Organic & Biomolecular Chemistry 18, no. 5 (2020): 905–11. http://dx.doi.org/10.1039/c9ob02398d.

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Lewis base-CO₂/COS adducts were firstly studied as organocatalysts for [4 + 2] annulation of CO₂/COS with allenamides to selectively synthesize 1,3-oxazine-2,4-diones/1,3-thiazine-2,4-diones.

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31

Park, Seok-Hwi, Xiangdan Jin, Jong-Cheol Kang, Changyoung Jung, Seong-Soo Kim, Sung-Soo Kim, Kee-Young Lee, and Won-Hun Ham. "Chirality extension of an oxazine building block en route to total syntheses of (+)-hyacinthacine A2 and sphingofungin B." Org. Biomol. Chem. 13, no. 15 (2015): 4539–50. http://dx.doi.org/10.1039/c5ob00251f.

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32

Liang, Y. C., X. A. Chen, L. Zhao, Q. Y. Zhang, J. X. Chen, Y. F. Ming, and M. G. Fan. "1,3,3-Trimethylindoline-2-spiro-2'-3'-methyl-2'H-phenanthro[9,10-b][1,4]oxazine." Acta Crystallographica Section C Crystal Structure Communications 54, no. 2 (February 15, 1998): 279–81. http://dx.doi.org/10.1107/s0108270197014637.

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33

Sun, X., Y. Liang, M. Fan, E. T. Knobbe, and E. M. Holt. "1-Methylbenzothiazolinospiro-2,3'-(2-methyl[3H]phenanthr[9,10-b][1,4]oxazine) and 1-Methylbenzothiazolinospiro-2,3'-(2'-methyl[3H]naphth[2,1-b][1,4]oxazine)." Acta Crystallographica Section C Crystal Structure Communications 53, no. 6 (June 15, 1997): 820–23. http://dx.doi.org/10.1107/s0108270197000012.

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34

Arnold, Zdeněk, and Dalimil Dvořák. "Benzylidenemalonaldehydes: Synthesis of 4-aryl-2-dimethylamino-4H-1,3-oxazine-5-carboxaldehyde." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2265–69. http://dx.doi.org/10.1135/cccc19852265.

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Reaction of substituted benzylidenemalonaldehydes Ia-Ic and thienylmethylenemalonaldehyde (Id) with dimethylcyanamide in boiling benzene afforded the corresponding 4-aryl-2-dimethylamino-4H-1,3-oxazine-5-carboxaldehydes III. Electronic requirements for this cyclization reaction are discussed in relation with general rules and further applicability.

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35

Sun, Yi, Wenfei Huang, Zhiqiang Li, Tao Wang, and Jin Luo. "Design, synthesis, and herbicidal activity of novel 2-(arylamino)-5-methyl-4-methylene-7-(methylthio)-4H-pyrido[4,3-d][1,3]oxazine-8-carbonitrile derivatives." Journal of Chemical Research 43, no. 3-4 (March 2019): 119–23. http://dx.doi.org/10.1177/1747519819845771.

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A series of 5-methyl-4-methylene-7-methylthio-2-arylmino-4 H-pyrido[4,3- d][1,3]oxazine-8-carbonitrile derivatives were synthesized via tandem aza-Wittig and annulation reactions with { N-[3-acetyl-5-cyano-2-methyl-6-(methylthio)pyridin-4-yl]imino}triphenylphosphorane and aryl isocyanate in dry dichloromethane. Their structures were clearly confirmed by infrared, 1H NMR, 13C NMR, high-resolution mass spectrometry, and X-ray single-crystal diffraction. All newly synthesized compounds were screened for herbicidal activities against monocotyledonous and dicotyledonous plants. The results indicated that the target compound 2-[(4-methoxyphenyl)amino]-5-methyl-4-methylene-7-(methylthio)-4 H-pyrido[4,3- d][1,3]oxazine-8-carbonitrile showed 100% inhibition rate to grain sorghum (monocotyledonous) at the concentration of 100 mg L−1.

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36

Lin, Andrew J. S., Cecilia C. Russell, Jennifer R. Baker, Shelby L. Frailey, Jennette A. Sakoff, and Adam McCluskey. "A facile hybrid ‘flow and batch’ access to substituted 3,4-dihydro-2H-benzo[b][1,4]oxazinones." Organic & Biomolecular Chemistry 14, no. 37 (2016): 8732–42. http://dx.doi.org/10.1039/c6ob01153e.

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37

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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38

Yang, Xu-Hong, Xiu-Ling Chen, Xiang-Ju Diao, and Ming-Hu Wu. "2-Benzyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine." Acta Crystallographica Section E Structure Reports Online 63, no. 7 (June 27, 2007): o3312. http://dx.doi.org/10.1107/s1600536807030188.

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39

El Kazzouli, S., G. Lavecchia, S. Berteina-Raboin, and G. Guillaumet. "Synthesis and functionalization of 2-hydroxypyrimido[4,5-b][1,4]oxazine." Tetrahedron Letters 47, no. 26 (June 2006): 4437–40. http://dx.doi.org/10.1016/j.tetlet.2006.04.051.

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40

Impellizzeri, Stefania, Sabrina Simoncelli, Chiara Fasciani, M. Luisa Marin, Geniece L. Hallett-Tapley, Gregory K. Hodgson, and Juan C. Scaiano. "Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly." Catalysis Science & Technology 5, no. 1 (2015): 169–75. http://dx.doi.org/10.1039/c4cy00703d.

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Solid niobium oxides (Nb₂O₅·nH₂O) and niobium phosphate were used as heterogeneous acid catalysts to promote the condensation between a switchable oxazine and a fluorescent coumarin in aprotic solvents.

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41

Anderson, Wayne K., and Deepak K. Dalvie. "Synthesis of 4-(2-chloroethyl)-2,3-dihydro[1,4]oxazino[2,3-b]quinoline and 4-(2-chloroethyl)2,3-dihydropyrido[2,3-b][1,4]oxazine." Journal of Heterocyclic Chemistry 30, no. 6 (December 1993): 1533–36. http://dx.doi.org/10.1002/jhet.5570300614.

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42

Kálmán, A., Gy Argay, G. Stájer, and G. Bernáth. "Structures of 4-phenylcyclohexa[e][1,3]oxazine-4H-2(3H)-thione and 2-chlorophenyl-4H-4-phenylcyclopenta[e][1,3]oxazine: an X-ray study." Journal of Molecular Structure 328 (December 1994): 245–51. http://dx.doi.org/10.1016/0022-2860(94)08384-3.

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43

Khanna, Garima, Komal Aggarwal, and Jitender M. Khurana. "An efficient and confluent approach for the synthesis of novel 3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-dione derivatives by a three component reaction in ionic liquid." RSC Advances 5, no. 58 (2015): 46448–54. http://dx.doi.org/10.1039/c5ra06169e.

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44

Haider, Malik Salman, Taufiq Ahmad, Mengshi Yang, Chen Hu, Lukas Hahn, Philipp Stahlhut, Jürgen Groll, and Robert Luxenhofer. "Tuning the Thermogelation and Rheology of Poly(2-Oxazoline)/Poly(2-Oxazine)s Based Thermosensitive Hydrogels for 3D Bioprinting." Gels 7, no. 3 (June 24, 2021): 78. http://dx.doi.org/10.3390/gels7030078.

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As one kind of “smart” material, thermogelling polymers find applications in biofabrication, drug delivery and regenerative medicine. In this work, we report a thermosensitive poly(2-oxazoline)/poly(2-oxazine) based diblock copolymer comprising thermosensitive/moderately hydrophobic poly(2-N-propyl-2-oxazine) (pPrOzi) and thermosensitive/moderately hydrophilic poly(2-ethyl-2-oxazoline) (pEtOx). Hydrogels were only formed when block length exceeded certain length (≈100 repeat units). The tube inversion and rheological tests showed that the material has then a reversible sol-gel transition above 25 wt.% concentration. Rheological tests further revealed a gel strength around 3 kPa, high shear thinning property and rapid shear recovery after stress, which are highly desirable properties for extrusion based three-dimensional (3D) (bio) printing. Attributed to the rheology profile, well resolved printability and high stackability (with added laponite) was also possible. (Cryo) scanning electron microscopy exhibited a highly porous, interconnected, 3D network. The sol-state at lower temperatures (in ice bath) facilitated the homogeneous distribution of (fluorescently labelled) human adipose derived stem cells (hADSCs) in the hydrogel matrix. Post-printing live/dead assays revealed that the hADSCs encapsulated within the hydrogel remained viable (≈97%). This thermoreversible and (bio) printable hydrogel demonstrated promising properties for use in tissue engineering applications.

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45

Barluenga, José, Fernando Aznar, Ramón Liz, María-Paz Cabal, Félix H. Cano, and Concepción Foces-Foces. "Oxidative aminomercuration of 2-propyn-1-ols. Stereoselective syntheses and structures ofcis-[1,4]oxazino[3,2-b]-1,4-oxazine derivatives." Chemische Berichte 119, no. 3 (March 1986): 887–99. http://dx.doi.org/10.1002/cber.19861190313.

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46

Sedlacek, Ondrej, and Richard Hoogenboom. "Drug Delivery Systems Based on Poly(2‐Oxazoline)s and Poly(2‐Oxazine)s." Advanced Therapeutics 3, no. 1 (December 16, 2019): 1900168. http://dx.doi.org/10.1002/adtp.201900168.

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47

?ankowska-Jasi?ska, W., M. Burgiel, A. Danel, and A. Sygula. "A novel synthesis of 1,3 Thiazetidine-2-one and 1,3-Oxazine-2-one Derivatives." Journal f�r Praktische Chemie 330, no. 5 (1988): 795–800. http://dx.doi.org/10.1002/prac.19883300516.

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48

Stasevych, M. V., S. I. Sabat, M. I. Semenyuk, R. Ya Musyanovych, and V. P. Novikov. "2-Aryl-4H-naphtho[2′,3′:4,5]thieno+− [2,3-d][1,3]oxazine-4,5,10-triones." Chemistry of Heterocyclic Compounds 44, no. 7 (July 2008): 897–98. http://dx.doi.org/10.1007/s10593-008-0131-4.

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49

LIANG, Y. C., X. A. CHEN, L. ZHAO, Q. Y. ZHANG, J. X. CHEN, Y. F. MING, and M. G. FAN. "ChemInform Abstract: 1,3,3-Trimethylindoline-2-spiro-2′-3′-methyl-2′H-phenanthro[9,10-b] [1,4]oxazine." ChemInform 29, no. 25 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199825048.

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50

Pancrazzi, Francesco, Elena Motti, Mirco Costa, Raffaella Mancuso, Bartolo Gabriele, and Nicola Della Ca’. "(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine." Molbank 2017, no. 1 (January 13, 2017): M927. http://dx.doi.org/10.3390/m927.

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