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Journal articles on the topic 'Oxazine chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Gaonkar, Santosh L., Vignesh U. Nagaraj, and Swarnagowri Nayak. "A Review on Current Synthetic Strategies of Oxazines." Mini-Reviews in Organic Chemistry 16, no. 1 (2018): 43–58. http://dx.doi.org/10.2174/1570193x15666180531092843.

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

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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

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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4

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 (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

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5

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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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 (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

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7

Sharma, Anupama, Sarita Khaturia, and Har Lal Singh. "Synthesis of New Schiff Base of 1,3-Oxazine and 1,3-Thiazine Derivatives Derived from 4-Phenyl Substituted Chalcones and Evaluation of their Antibacterial Activity." Asian Journal of Chemistry 33, no. 3 (2021): 531–36. http://dx.doi.org/10.14233/ajchem.2021.23050.

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Oxazine and thiazine heterocycles have distinctive interests due to their important class of natural and non-natural products and exhibit high biological activities in the pharmaceutical and biological fields. This work was planned to synthesize Schiff base of 1,3-oxazine and 1,3-thiazine derivative from 4-phenyl substituted chalcones. The structures of the newly synthesized targeted compounds were established from UV, IR, 1H NMR, 13C NMR and DFT calculations. The molecular properties HOMO-LUMO energy, energy gap, softness and harness were calculated using DFT/B3LYP/6-311G (d,p) basis set. in

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8

Mahmoud, Naglaa F. H., Eman A. El-Bordany, and Galal A. Elsayed. "Synthesis and Pharmacological Activities of Pyrano[2,3-d]pyrimidine and Pyrano[2,3-d]pyrimidine-5-one Derivatives as New Fused Heterocyclic Systems." Journal of Chemistry 2017 (2017): 1–7. http://dx.doi.org/10.1155/2017/5373049.

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Various fused oxazine such as 4-(4-methoxyphenyl)-3,7-dimethyl-1,4-dihydro-5H-pyrazolo [4′,3′:5,6]pyrano[2,3-d][1,3]oxazin-5-one2has been prepared and utilized as a starting material for novel pyrazolopyranopyrimidinones3,5,6, and7a–cand pyrazolopyranopyrimidines4,9,10, and11which are expected to possess considerable chemical and pharmacological activities. The structures of the new compounds have been elucidated by spectroscopic data and elemental analysis. The antioxidant and anticancer activities of synthesized products have been evaluated.

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9

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 (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

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10

Miri, Morteza, and Alireza Hassanabadi. "One-Pot and Three-Component Condensation of Kojic Acid with Aromatic Aldehydes and Methyl Carbamate: Synthesis of Pyrano-1,3-Oxazine Derivatives in Aqueous Media." Journal of Chemical Research 42, no. 8 (2018): 416–18. http://dx.doi.org/10.3184/174751918x15341755203029.

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A novel method for oxazine ring formation has been established using the reaction of kojic acid and aromatic aldehydes with methyl carbamate in the presence of p-toluenesulfonic acid in aqueous media to afford 4-aryl-6-hydroxymethyl-1,4-dihydropyrano[3,2-e][1,3] oxazine-2,8-diones in excellent yields. The present method does not involve any hazardous organic solvent. Therefore, this procedure could be classified as green chemistry.

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11

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 (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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12

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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13

Myeong, In-Soo, Changyoung Jung, and Won-Hun Ham. "Total Syntheses of (–)-7-epi-Alexine and (+)-Alexine Using Stereoselective Allylation." Synthesis 51, no. 18 (2019): 3471–76. http://dx.doi.org/10.1055/s-0037-1611566.

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Total syntheses of (–)-7-epi-alexine and (+)-alexine were achieved by using stereoselective allylation via a functionalized pyrrolidine obtained from an extended chiral 1,3-oxazine. The synthetic strategies include pyrrolidine formation via oxazine cleavage and diastereoselective allylations of a pyrrolidine aldehyde. (–)-7-epi-Alexine and (+)-alexine were synthesized from anti,syn,anti-oxazine in 12 steps.

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14

Brouillette, Yann, Jean Martinez, and Vincent Lisowski. "Chemistry of Ring-Fused Oxazine-2,4-diones." European Journal of Organic Chemistry 2009, no. 21 (2009): 3487–503. http://dx.doi.org/10.1002/ejoc.200801007.

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15

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 (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 func

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16

Brulíková, Lucie, Aidan Harrison, Marvin J. Miller, and Jan Hlaváč. "Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes." Beilstein Journal of Organic Chemistry 12 (September 1, 2016): 1949–80. http://dx.doi.org/10.3762/bjoc.12.184.

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The hetero-Diels–Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.

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17

Haider, Malik Salman, Taufiq Ahmad, Mengshi Yang, et al. "Tuning the Thermogelation and Rheology of Poly(2-Oxazoline)/Poly(2-Oxazine)s Based Thermosensitive Hydrogels for 3D Bioprinting." Gels 7, no. 3 (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

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18

Claveau, Elise, Isabelle Gillaizeau, Jérome Blu, Amélie Bruel, and Gérard Coudert. "Easy Access to New Heterocyclic Systems: 1,4-Oxazine and Substituted 1,4-Oxazines." Journal of Organic Chemistry 72, no. 13 (2007): 4832–36. http://dx.doi.org/10.1021/jo070528n.

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19

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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20

Fišera, Lubor, Marta Konopíková, Ladislav Štibrányi, and Hans-Joachim Timpe. "Solvent and substituent effects on rearrangement of 4-(4-X-phenyl)-2,7-dioxa-3-azabicyclo[3,3,0]oct-3-enes." Collection of Czechoslovak Chemical Communications 50, no. 9 (1985): 1971–81. http://dx.doi.org/10.1135/cccc19851971.

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Preparation of the title compounds V is described. They give, on irradiation, the 2,3-dihydro-6H-1,3-oxazine derivatives VI as the main products besides the tetrahydrofuro[3,4-d]oxazoline derivatives VII. The VI to VII product ratio depends on the substituent bound to the aromatic residue. Polar solvents favour formation of the VI derivatives in the order Cl >H > CH3. In non-polar solvents the proportion of VII is increased. The quantum yields of the photoreaction vary within the limits from 0.006 to 0.04 (H >F > Cl > CH3 > OCH3).

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21

Lin, Ching Hsuan, Chun Kai Chien, Chien Han Chen, and Tzong Yuan Juang. "Photo-sensitive benzoxazine II: chalcone-containing benzoxazine and its photo and thermal-cured thermoset." RSC Advances 7, no. 60 (2017): 37844–51. http://dx.doi.org/10.1039/c7ra06967g.

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Chalcone-containing benzoxazine (BHP-a) was synthesized. Two procedures were applied to cure BHP-a, thermal curing of chalcone and oxazine moieties. Another one was photo curing the chalcone moiety, followed by thermal curing of the oxazine moiety.

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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 (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

Brolo, Alexandre G., and Aaron C. Sanderson. "Surface-enhanced Raman scattering (SERS) from a silver electrode modified with oxazine 720." Canadian Journal of Chemistry 82, no. 10 (2004): 1474–80. http://dx.doi.org/10.1139/v04-117.

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Electrochemical and spectroelectrochemical data was obtained for a silver electrode modified with oxazine 720 immersed in 0.2 mol L1 KCl solution. A quasi-reversible redox behaviour was observed for the modified electrode. The electrochemical charges, obtained during either the anodic or the cathodic processes, were higher than expected for a monolayer of flat-adsorbed oxazine 720. Surface-enhanced Raman scattering (SERS) was recorded in situ for different applied potentials. Although the tilt angle was not determined, the analysis of the most enhanced vibrational modes in the SERS data, in c

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24

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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25

Bouché, Léa, and Hans-Ulrich Reissig. "Synthesis of novel carbohydrate mimetics via 1,2-oxazines." Pure and Applied Chemistry 84, no. 1 (2011): 23–36. http://dx.doi.org/10.1351/pac-con-11-09-20.

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The combination of lithiated alkoxyallenes with carbohydrate-derived nitrones constitutes a flexible entry to highly functionalized enantiopure 1,2-oxazine derivatives. They can be used as precursors for acyclic and cyclic carbohydrate-like products such as amino sugar alcohols, azetidine and pyrrolidine derivatives. The Lewis acid-promoted rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines to bicyclic compounds allows an efficient route to novel amino pyran and oxepane derivatives. After subsequent transformations, new carbohydrate mimetics or “real” carbohydrates were obtained in good

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26

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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27

Bloksma, Meta M., Renzo M. Paulus, Huub P. C. van Kuringen, et al. "Thermoresponsive Poly(2-oxazine)s." Macromolecular Rapid Communications 33, no. 1 (2011): 92–96. http://dx.doi.org/10.1002/marc.201100587.

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28

Lim, Byeong-Yun, Chang-Heon Suhl, and Cheon-Gyu Cho. "Synthesis of Oxazine-Embedded 1,1′-Biaryl-2,2′-diamine via [3,3]-Sigmatropic Rearrangement of Oxazine Diarylhydrazine." Bulletin of the Korean Chemical Society 37, no. 8 (2016): 1171–72. http://dx.doi.org/10.1002/bkcs.10871.

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29

Akiba, Masaharu, Alexander S. Dvornikov, and Peter M. Rentzepis. "Formation of oxazine dye by photochemical reaction of N-acyl oxazine derivatives." Journal of Photochemistry and Photobiology A: Chemistry 190, no. 1 (2007): 69–76. http://dx.doi.org/10.1016/j.jphotochem.2007.03.014.

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30

Cowper, Nicholas G. W., Matthew J. Hesse, Katie M. Chan, and Sarah E. Reisman. "A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core." Chemical Science 11, no. 43 (2020): 11897–901. http://dx.doi.org/10.1039/d0sc04802j.

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31

Wilkinson, Francis, Graeme P. Kelly, Luis F. Vieira Ferreira, Victor M. M. R. Freire, and M. Isabel Ferreira. "Benzophenone sensitization of triplet oxazine and of delayed fluorescence by oxazine in acetonitrile solution." Journal of the Chemical Society, Faraday Transactions 87, no. 4 (1991): 547. http://dx.doi.org/10.1039/ft9918700547.

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32

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 (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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33

Bougan, Sabereh, and Alireza Hassanabadi. "Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate." Journal of Chemical Research 41, no. 3 (2017): 136–38. http://dx.doi.org/10.3184/174751917x14859570937758.

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A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.

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34

Neidlein, Richard, Zhijun Wang, and Walter Kramer. "Syntheses and Structure Elucidation of Dimethylaminovinyl Substituted 1,3-Oxazines and Pyrazolo[3,4-d][3,1]oxazine Derivatives." HETEROCYCLES 51, no. 12 (1999): 2893. http://dx.doi.org/10.3987/com-99-8696.

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35

Reddy, Valluru Krishna, Hideto Miyabe, Masashige Yamauchi, and Yoshiji Takemoto. "Enantioselective synthesis of [1,2]-oxazinone scaffolds and [1,2]-oxazine core structures of FR900482." Tetrahedron 64, no. 6 (2008): 1040–48. http://dx.doi.org/10.1016/j.tet.2007.07.071.

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36

Upton, A. M., S. Cho, T. J. Yang, et al. "In VitroandIn VivoActivities of the Nitroimidazole TBA-354 against Mycobacterium tuberculosis." Antimicrobial Agents and Chemotherapy 59, no. 1 (2014): 136–44. http://dx.doi.org/10.1128/aac.03823-14.

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ABSTRACTNitroimidazoles are a promising new class of antitubercular agents. The nitroimidazo-oxazole delamanid (OPC-67683, Deltyba) is in phase III trials for the treatment of multidrug-resistant tuberculosis, while the nitroimidazo-oxazine PA-824 is entering phase III for drug-sensitive and drug-resistant tuberculosis. TBA-354 (SN31354[(S)-2-nitro-6-((6-(4-trifluoromethoxy)phenyl)pyridine-3-yl)methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine]) is a pyridine-containing biaryl compound with exceptional efficacy against chronic murine tuberculosis and favorable bioavailability in preliminary r

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37

Zhang, Lei, Yejun Zhu, Dan Li, Min Wang, Haibin Chen, and Jingshen Wu. "Preparation and characterization of fully renewable polybenzoxazines from monomers containing multi-oxazine rings." RSC Advances 5, no. 117 (2015): 96879–87. http://dx.doi.org/10.1039/c5ra17164d.

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38

Fleming, Scott, Andrew Mills, and Tell Tuttle. "Predicting the UV–vis spectra of oxazine dyes." Beilstein Journal of Organic Chemistry 7 (April 15, 2011): 432–41. http://dx.doi.org/10.3762/bjoc.7.56.

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In the current work we have investigated the ability of time-dependent density functional theory (TD-DFT) to predict the absorption spectra of a series of oxazine dyes and the effect of solvent on the accuracy of these predictions. Based on the results of this study, it is clear that for the series of oxazine dyes an accurate prediction of the excitation energy requires the inclusion of solvent. Implicit solvent included via a polarizable continuum approach was found to be sufficient in reproducing the excitation energies accurately in the majority of cases. Moreover, we found that the SMD sol

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39

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 (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 indicate

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Machado, Irlaine, Isabel Hsieh, Eric Rachita, et al. "A truly bio-based benzoxazine derived from three natural reactants obtained under environmentally friendly conditions and its polymer properties." Green Chemistry 23, no. 11 (2021): 4051–64. http://dx.doi.org/10.1039/d1gc00951f.

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41

NAKAMURA, Masataka, and Takashi TANIGUCHI. "Synthesis and Characteristic of Spiro-oxazine Compounds." Journal of Synthetic Organic Chemistry, Japan 49, no. 5 (1991): 392–402. http://dx.doi.org/10.5059/yukigoseikyokaishi.49.392.

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42

Kawauchi, Susumu, Haruo Yoshida, Naoko Yamashina, Manabu Ohira, Shigeru Saeda, and Masahiro Irie. "A New Photochromic Spiro[3H-1,4-oxazine]." Bulletin of the Chemical Society of Japan 63, no. 1 (1990): 267–68. http://dx.doi.org/10.1246/bcsj.63.267.

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43

Sabnis, Ram W. "Novel Oxazine Monoacylglycerol Lipase (MAGL) Inhibitors." ACS Medicinal Chemistry Letters 12, no. 3 (2021): 312–13. http://dx.doi.org/10.1021/acsmedchemlett.1c00055.

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44

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

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45

Chaskar, Atul, Vimal Vyavhare, Vikas Padalkar, Kiran Phatangare, and Hrushikesh Deokar. "An environmentally benign one-pot synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one derivatives catalysed by phosphomolybdic acid." Journal of the Serbian Chemical Society 76, no. 1 (2011): 21–26. http://dx.doi.org/10.2298/jsc100410016c.

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A phosphomolybdic acid catalysed novel method for the synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one derivatives by a one-pot, three-component reaction of ?-naphthol, aromatic aldehydes and urea in excellent yields is described.

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46

Pattaweepaiboon, Supak, Natchayapak Phiromphu, Narongpol Kaewchangwat, Khomson Suttisintong, and Weekit Sirisaksoontorn. "An indolino-spironaphthooxazine probe for colorimetric detection of ferric ions in drinking water." New Journal of Chemistry 45, no. 25 (2021): 11284–91. http://dx.doi.org/10.1039/d1nj01166a.

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The sensing performance of a novel indolino-spironaphthooxazine derivative (SPNO), 6′(3,4-dihydroisoquinolin-2(1H)-yl)-3,3-dimethyl-1-phenethylspiro[indoline-2,3′-naphtho[2,1-b][1,4]oxazine], was investigated for rapid colorimetric detection of ferric ions (Fe<sup>3+</sup>) in drinking water.

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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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Kjær, Christina, and Steen Brøndsted Nielsen. "Luminescence spectroscopy of oxazine dye cations isolated in vacuo." Physical Chemistry Chemical Physics 21, no. 8 (2019): 4600–4605. http://dx.doi.org/10.1039/c8cp07340f.

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Gupta, Nidhi, Sonia Sharma, Arun Raina, Nisar A. Dangroo, Shashi Bhushan, and Payare L. Sangwan. "Synthesis and anti-proliferative evaluation of novel 3,4-dihydro-2H-1,3-oxazine derivatives of bakuchiol." RSC Advances 6, no. 108 (2016): 106150–59. http://dx.doi.org/10.1039/c6ra23757f.

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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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