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1.
M. N. Khimich F. E. Gostev I. V. Shelaev O. M. Sarkisov E. A. Birgen B. M. Bolotin B. M. Uzhinov 《High Energy Chemistry》2010,44(6):482-491
Femtosecond dynamics of processes in the excited state of 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones has been studied by femtosecond
absorption spectroscopy. The rate constants of intramolecular photoinduced proton transfer (IPPT) have been determined for
the N-substituted derivatives (0.7–11 ps−1). The IPPT rate constant depends on the inductive constant of the substituent and the potential barrier height, which was
calculated by a quantum-chemical method (TDDFT). The multiexponential character of the kinetics of photoinduced absorption
by the compounds with a low inductive constant of the N-substituent in the spectral region of the S1 → SN absorption and the stimulated emission of the IPPT product is explained by the rapid (∼10 ps−1) relaxation process preceding the IPPT. 相似文献
2.
Fluorescence spectra of N-substituted 2-(2-aminophenyl)-4H-3,1-benzoxazin-4-ones consist of two bands, the long-wavelength band with anomalous Stokes shift, which corresponds to the emission of the product of intramolecular photoinduced proton transfer, and the short-wavelength band belonging to the form in which proton transfer does not occur. It is assumed that there is equilibrium between two planar rotamers in the ground state: one with the N-H…N hydrogen bond in which the intramolecular photoinduced proton transfer occurs and the other with the N-H…O bond, which does not experience hydrogen transfer. According to ab initio quantum-chemical calculations, the potential energy of proton transfer in the first excited singlet state has a potential barrier of 2.1–26.8 kJ/mol depending on the electron-withdrawing ability of the substituent on the amino group. 相似文献
3.
M. V. Loseva B. M. Bolotin G. A. Bogdanova B. M. Krasovitskii 《Chemistry of Heterocyclic Compounds》1972,8(5):557-561
Nitro-substituted 2-phenyl- and 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-ones were synthesized. The UV, IR, and luminescence spectra were studied. The position of the nitro group affects the strength of the intramolecular hydrogen bond (IHB). The luminescence properties of nitro-substituted 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-ones are associated with the strength of the IHB. The luminescence maximum is shifted to the short-wave region as the IHB becomes stronger.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 616–621, May, 1972. 相似文献
4.
4H-3,1-Benzoxazin-4-ones methoxy-substituted 2-(2-arenesulfonylaminophenyl)-4H-3,1-benzoxazin-4-ones
M. V. Loseva B. M. Bolotin B. M. Krasovitskii 《Chemistry of Heterocyclic Compounds》1971,7(8):964-967
Methoxy-substituted 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-one and 2-phenyl-4H-3,1-benzoxazin-4-one were synthesized. Their UV, IR, and luminescence spectra were studied. The position of the methoxy group affects the strength of the intramolecular hydrogen bond (IHB). The luminescence properties of methoxy-substituted 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-ones are associated with the strength of the IHB. The luminescence maximum is shifted to the short-wave region with strengthening of the IHB, and the luminescence intensity increase simultaneously.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1028–1032, August, 1971.The authors thank Yu. S. Ryabokobylko and A. O. Zisman for measuring the absorption spectra in the IR and UV regions. 相似文献
5.
13C chemical shifts of nine N-substituted 2-amino-4H-3,1-benzoxazin-4-ones, the isomeric 3-substituted 2,4-(1H,3H)quinazolinediones, and the parent compounds of the two series are reported. Support is provided for the endocyclic position of the C=N bond in the former series of compounds. 相似文献
6.
Cyril Prknyi Hui Liang Yuan Bo H. E. Strmberg Ariella Evenzahav 《Journal of heterocyclic chemistry》1992,29(4):749-753
The synthesis of ten new substituted 1,3,4-thiadiazolyl-4(3H)-quinazolinones 8–11, 13, 17 , and 20–23 is reported. Compounds 8–11 were prepared by condensation of 5-fluoro-2-methyl-3,1-benzoxazin-4-one (3) and 5-substituted 2-amino-1,3,4-thiadiazoles 4–7. Compound 13 was obtained by condensation of 5-fluoro-2-methyl-3,1-benzoxazin-4-one (3) with DL-α-amino-?-caprolactam (12) . Compound 17 was synthesized by condensation of 6-bromo-2-methyl-3,1-benzoxazin-4-one (16) and 2-amino-5-t-butyl-1,3,4-thiadiazole (5) . Compounds 20–23 were obtained by condensation of 5-chloro-6,8-dibromo-2-methyl-3,1-benzoxazin-4-one (19) and 5-substituted 2-amino-1,3,4-thiadiazoles 4–7, respectively. The substituted 3,1-benzoxazin-4-ones 3, 16, and 19 were obtained in good yield by refluxing the appropriate anthranilic acid, 1,15 , and 18 with acetic anhydride (2) . 相似文献
7.
François Clémence Odile Le Martret Jeannine Collard 《Journal of heterocyclic chemistry》1984,21(5):1345-1353
The synthesis of N-aryl and N-heteroaryl substituted 4-hydroxy-3-quinolinecarboxamides 1 is described. The attack of dianions 12 of N-aryl substituted acetamides on the C-4 carbonyl of 4H-3,1-benzoxazin-4-ones 11 gave rise to ketoamides 13 , which smoothly cyclised in the presence of bases to afford quinolinecarboxamides 1 . By this method, a large number of 2-substituted 4-hydroxyquinolinecarboxamides can be prepared. 相似文献
8.
B. M. Bolotin L. S. Zeryukina R. U. Safina V. V. Egorkin R. I. Kuliev 《Chemistry of Heterocyclic Compounds》1981,17(10):996-998
2,6-Disubstituted 4H-3,1-benzoxazin-4-ones that have mesogenic properties were synthesized by the reaction of 5-substituted anthranilic acid with aroyl chlorides in pyridine. The introduction of a 4H-3,1-benzoxazin-4-one fragment increases the absolute value of the anisotropy of the dielectric permeability. The temperatures and heats of the phase transitions are presented.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1335–1337, October, 1981. 相似文献
9.
Avetisyan A. A. Aleksanyan I. L. Pivazyan A. A. 《Russian Journal of Organic Chemistry》2003,39(8):1164-1166
From 4-hydroxy-2-methylquinoline-3-propionyl chlorides hydrochlorides the corresponding thiosemicarbazides were synthesized. The cyclization of the latter both in alkaline and acidic media furnished 4-hydroxy-2-methyl-3-[2-(5-mercapto-1H-1,2,4-triazol-3-yl)ethyl]quinolines. The reaction of the above propionyl chlorides with anthranilic acid afforded the corresponding 2-[2-(4-hydroxy-2-methyl-3-quinolyl)ethyl]-4H-3,1-benzoxazin-4-ones. 相似文献
10.
2-(3-Nitrophenyl)-4H-3,1-benzoxazin-4-one is formed in the nitration of 2-phenyl-4H-3,1-benzoxazin-4-one, while 2-(2-tosylamino-5-nitrophenyl)-4H-3,1-benzoxazin-4-one is formed in the nitration of 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-one.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 908–909, July, 1974. 相似文献
11.
A convenient synthetic approach to 2-[1-(dialkylamino)alkyl]-4H-3,1-benzoxazin-4-ones has been developed. Thus, 1,1-dimethylethyl 2-isocyanobenzoates, which can be readily prepared from 2-nitrobenzoic acids by a simple four-step sequence, react with N,N-dialkyliminium iodides without using any catalysts under mild conditions to give the desired products in generally fair-to-good yields. 相似文献
12.
An efficient synthesis of N-phenylcarboxamodo-2-aryl-1,2-dihydro-(4H)-3,1-benzoxazin-4-ones is described by cyclization reaction of some 2-(benzylidene-amino)-benzoic acids with phenyl isocyanate under reflux conditions in CHCl3. Higher yields of the products were produced in high purity with simple work-up. 相似文献
13.
Khosrow Jadidi Ramin Ghahremanzadeh Morteza Mehrdad Mohammad Ghanbari Hamid Arvin-Nezhad 《Monatshefte für Chemie / Chemical Monthly》2008,139(3):277-280
Summary. Novel N-alkyl-4-imino-1,4-dihydro-2H-3,1-benzoxazin-2-ones were synthesized in a single step by Baeyer–Villiger oxidation of N-alkyl-3-imino-2-indolinone derivatives in high yields. The structures of the products were determined by spectral data and
by X-ray diffraction. Besides their novel structures, these compounds may have important biological activities and industrial
applications. 相似文献
14.
T. V. Trashakhova E. V. Nosova M. S. Valova P. A. Slepukhin G. N. Lipunova V. N. Charushin 《Russian Journal of Organic Chemistry》2011,47(5):753-761
trans-2-Styryl-substituted 3H-, 3-phenyl-, and 3-naphthylquinazolin-4-ones and their 6,7-difluoro derivatives were synthesized by condensation of appropriate
2-methylquinazolin-4-ones with aromatic aldehydes or by the transformation of the heterocycle of 2-methyl-3,1-benzoxazin-4-one
under the action of benzylidenephenylamines. 相似文献
15.
Summary 2-Benzoylamino-6,7-dimethoxy-4H-3,1-benzoxazin-4-one was prepared by thermal treatment of 2-(3-benzoylthioureido)-4,5-dimethoxybenzoic acid and by benzoylation of 2-amino-6,7-dimethoxy-4H-3,1-benzoxazin-4-one. The inactivation of chymotrypsin and human leukozyte elastase by the title compound and 2-benzoylamino-4H-3,1-benzoxazin-4-one is reported.
2-Benzoylamino-6,7-dimethoxy-4H-3,1-benzoxazin-4-on: Synthese und Untersuchung der Inaktivierung von Serin-Proteasen
Zusammenfassung 2-Benzoylamino-6,7-dimethoxy-4H-3,1-benzoxazin-4-on wurde durch thermische Behandlung von 2-(3-Benzoylthioureido)-4,5-dimethoxybenzoesäure und durch Benzoylierung von 2-Amino-6,7-dimethoxy-4H-3,1-benzoxazin-4-on hergestellt. Über die Inaktivierung von Chymotrypsin und humaner Leukozyten-Elastase durch die Titelverbindung und 2-Benzoylamino-4H-3,1-benzoxazin-4-on wird berichtet.相似文献
16.
V. I. Kelarev M. A. Silin V. N. Koshelev O. A. Borisova 《Chemistry of Heterocyclic Compounds》2004,40(5):616-621
A series of 2-substituted and 2,3-disubstituted quinazolin-4-ones containing a 3,5-di(tert-butyl)-4-hydroxyphenyl group has been synthesized. They were prepared by the condensation of carboxylic acid imino ester hydrochlorides containing the indicated fragment with ethyl anthranilate and also by the reaction of azomethines, N-acylhydrazones, or the 4-phenylthiosemicarbazone of 3,5-di(tert-butyl)-4-hydroxybenzaldehyde with 2-methyl-4H-2,1-benzoxazin-4-one. 相似文献
17.
Harutyunyan A. A. Gukasyan G. T. Panosyan H. A. Tamazyan R. A. Ayvazyan A. G. Danagulyan G. G. 《Russian Journal of Organic Chemistry》2019,55(9):1363-1369
Russian Journal of Organic Chemistry - The reaction of 2-methyl-4H-3,1-benzoxazin-4-one and its 6-iodo derivatives with a number of amines in polyphosphoric acid afforded 3- and 3,6-substituted... 相似文献
18.
E. S. Vostrov A. A. Novikov A. N. Maslivets Z. G. Aliev 《Russian Journal of Organic Chemistry》2007,43(2):224-227
2-Carboxyphenylamides of aroylacetic acids undergo cyclization when treated with dehydrating agents to give 2-[(Z)-2-aryl-2-hydroxy-1-ethenyl]-4H-3,1-benzoxazin-4-ones. Crystal and molecular structure of the latter phenyl derivative was studied by X-ray crystallography.
Original Russian Text ? E.S. Vostrov, A.A. Novikov, A.N. Maslivets, Z.G. Aliev, 2007, published in Zhurnal Organicheskoi Khimii,
2007, Vol. 43, No. 2, pp. 232–235. 相似文献
19.
Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently substituted with amino derivatives to obtain the 3H-quinazolin-4-ones. The herbicidal evaluation was performed on the model plants barnyard grass (a monocotyledon) and rape (a dicotyledon), and most of the title compounds displayed high levels of phytotoxicity. The active substructure and inhibitory phenotype analysis indicated that these compounds could be attributed to the class of plant hormone inhibitors. A docking study of several representative compounds with the hormone receptor TIR1 revealed an appreciable conformational match in the active site, implicating these compounds are potential lead hits targeting this receptor. 相似文献
20.
I. V. Ukrainets P. A. Bezuglyi V. I. Treskaya A. V. Turov S. V. Slobodzyan O. V. Gorokhova 《Chemistry of Heterocyclic Compounds》1991,27(8):907-909
3-Amino-2-carboxymethylquinazolin-4(3H)-one was obtained by hydrazinolysis of 2-carbethoxymethyl-4H-3,1-benzoxazin-4-one. Its transformations into 2-hydroxypyrazolo[5,1-b]quinazolin-9(1H)-oneand3-amino-2-hydrazido-(orbenzylamido)carbonylmethylquinazoline-4(3H)-ones were studied.For Communication 1, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1128–1130, August, 1991. 相似文献