New Synthesis of Naphtho- And Benzoxazoles: Decomposition of Naphtho- And Benzoxazinones With Koh

Saitz, Claudio; Rodríguez, Hernán B.; Márquez, Amelia; Cañete, Álvaro; Jullian, Carolina; Zanocco, Antonio L.

doi:10.1081/scc-100000190

Cited by 27 publications

(12 citation statements)

References 15 publications

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“…In spite of the wide range of basic and innovative research that has been developed having as center the emissive properties of benzoxazole, no reports describe the photophysics and/or the photochemistry of compounds with the oxazole heterocycle condensed to extended aromatic systems. There are a variety of synthetic methods to obtain naphthoxazole derivatives , however, the only study related to naphthoxazole photophysics involves the use of 1,2‐naphthozaxoles as substitutes for the benzoxazole residue in merocyanine 540. This change increases the fluorescence and triplet yields and decreases concomitantly the yield for photoisomerization .…”

Section: Introductionmentioning

confidence: 99%

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Curitol

Ragàs

Nonell

et al. 2013

Photochem & Photobiology

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The photophysical properties of 2-phenyl-naphtho[1,2-d][1,3]oxazole, 2(4-N,N-dimethylaminophenyl)naphtho[1,2-d][1,3]oxazole and 2(4-N,N-diphenylaminophenyl) naphtho[1,2-d][1,3]oxazole were studied in a series of solvents. UV-Vis absorption spectra are insensitive to solvent polarity whereas the fluorescence spectra in the same solvent set show an important solvatochromic effect leading to large Stokes shifts. Linear solvation energy relationships were employed to correlate the position of fluorescence spectra maxima with microscopic empirical solvent parameters. This study indicates that important intramolecular charge transfer takes place during the excitation process. In addition, an analysis of the solvatochromic behavior of the UV-Vis absorption and fluorescence spectra in terms of the Lippert-Mataga equation shows a large increase in the excited-state dipole moment, which is also compatible with the formation of an intramolecular charge-transfer excited state. We propose both naphthoxazole derivatives as suitable fluorescent probes to determine physicochemical microproperties in several systems and as dyes in dye lasers; consequence of their high fluorescence quantum yields in most solvents, their large molar absorption coefficients, with fluorescence lifetimes in the range 1-3 ns as well as their high photostability.

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Section: Introductionmentioning

confidence: 99%

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Curitol

Ragàs

Nonell

et al. 2013

Photochem & Photobiology

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“…Under basic conditions, the phenyloxazinone 5 was rapidly converted into the phenyloxazole 6 as reported recently by us for simpler model systems. 9 The synthetic scheme is shown in Scheme 1. (5) heterocyclic systems.…”

Section: Resultsmentioning

confidence: 99%

Oxazine‐ and oxazole‐fused derivatives of the alkaloid boldine and their complete structural and spectral assignments by HMQC and HMBC experiments

Sobarzo‐Sánchez¹,

Cassels²,

Saitz-Barria³

et al. 2001

Magnetic Reson in Chemistry

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The novel heterocycles 1,11-dimethoxy-2-hydroxy-6-methyloxazolo[4,5-k]-5,6,6a,7-tetrahydro-4H-dibenzo [de,g]quinoline, 1,12-dimethoxy-2-hydroxy-6-methyl-9-phenyl-10H-oxazin[5,6-k]-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-10-one and 1,11-dimethoxy-2-hydroxy-6-methyl-9-phenyloxazolo[4,5-k]-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline were prepared starting from the alkaloid boldine. The structures were confirmed and the 1 H and 13 C NMR spectra were completely assigned using a combination of one-and two-dimensional NMR techniques.

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“…reported the synthesis of naphtho[2,1‐ d ]oxazoles by the condensation of 2‐aminonaphthalene‐1‐ol with aromatic aldehydes in the presence of Pb(OAc) 4 (Scheme , I). Condensation of 2‐aminonaphthalene‐1‐ol and aldehydes provided the corresponding azomethines and subsequent oxidation produced naphtho[2,1‐ d ]oxazoles (Scheme , II), as did rearrangement of naphthoxazinones under basic conditions (Scheme , III) and the reaction of 2‐(hydroxyimino)naphthalen‐1(2 H )‐one with benzyl bromide in the presence of triethylamine (Scheme , IV)…”

Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed C−H Oxygenation of Benzoxepine‐4‐carboxylates: Facile Synthesis and Photophysical Properties of Naphtho[2,1‐d]oxazoles and Benzo[c]phenoxazines

et al. 2016

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An efficient, solvent-free, one-pot protocolw as developed for the preparation of naphtho[2,1-d]oxazoles and benzo[c]phenoxazines by the CÀHo xygenation of benzoxepine-4-carboxylates with benzylamines and anilinesi nt he presence of Cu(OAc) 2 .T he synthesis, UV/vis absorption, fluorescence emission and electrochemical properties have been studied for these heterocyclic compounds. The benzo[c]phenoxazines absorbed in the UV/vis in the range 449-461 nm and fluorescencee mission in the range 562-627 nm. The nitro-andd imethyl-substituted benzo[c]phenoxazines had the most favorablef luorescencee mission in these series of compounds (emission maximaa t6 27 and6 03 nm with quantum yields F f = 0.51 and 0.37, respectively). The optical and electrochemical properties suggest that these compounds can act as electron-transporting materialsf or organic light-emitting diode applications.Scheme1.Previouswork on the synthesis of naphtha[2,1-d]oxazoles, 7 Hbenzo[c]phenoxazines,a nd this work.[a] K.

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New Synthesis of Naphtho- And Benzoxazoles: Decomposition of Naphtho- And Benzoxazinones With Koh

Cited by 27 publications

References 15 publications

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives

Oxazine‐ and oxazole‐fused derivatives of the alkaloid boldine and their complete structural and spectral assignments by HMQC and HMBC experiments

Copper‐Catalyzed C−H Oxygenation of Benzoxepine‐4‐carboxylates: Facile Synthesis and Photophysical Properties of Naphtho[2,1‐d]oxazoles and Benzo[c]phenoxazines

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