- Palladium-Catalyzed Carbonylative Difunctionalization of C=N Bond of Azaarenes or Imines to Quinazolinones
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Supporting information for this article is given via a link at the end of the document. By intercepting the acylpalladium species with C=N bond of azaarenes or imines other than free amines or alcohols, the difunctionalization of C=N bond was established via palladium-catalyzed carbonylation/nucleophilic addition sequence. This method is compatible with a diverse range of azaarenes and imines and allows for the efficient synthesis of a wide range of quinazolinones and derivatives. The synthetic utility has been demonstrated by one-step synthesis of evodiamine and its analogue with inexpensive starting materials.
- Zhou, Xibing,Ding, Yongzheng,Huang, Hanmin
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p. 1678 - 1682
(2020/05/05)
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- Synthesis, 2D-QSAR studies and biological evaluation of quinazoline derivatives as potent anti-trypanosoma cruzi agents
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Background: Chagas disease affects about 7 million people worldwide. Only two drugs are currently available for the treatment for this parasite disease, namely, benznidazol (Bzn) and nifurtimox (Nfx). Both drugs have limited curative power in the chronic phase of the disease. Therefore, continuous research is an urgent need so as to discover novel therapeutic alternatives. Objective: The development of safer and more efficient therapeutic anti-T. cruzi drugs continues to be a major goal in trypanocidal chemotherapy. Method: Synthesis, 2D-QSAR and drug-like physicochemical properties of a set of quinazolinone and quinazoline derivatives were studied as trypanocidal agents. All compounds were screened in vitro against Trypanosoma cruzi (Tulahuen strain, Tul 2 stock) epimastigotes and bloodstream trypomastigotes. Results: Out of 34 compounds synthesized and tested, six compounds (5a, 5b, 9b, 9h, 13f and 13p) displayed significant activity against both epimastigotes and tripomastigotes, without exerting toxicity on Vero cells. Conclusion: The antiprotozoal activity of these quinazolinone and quinazoline derivatives represents an interesting starting point for a medicinal chemistry program aiming at the development of novel chemotherapies for Chagas disease.
- Battini, Leandro,Bollini, Mariela,Bruno, Ana M.,Casal, Juan J.,Lombardo, María E.,Ni?o, María E.,Puente, Vanesa R.,Sasiambarrena, Leandro D.,Valdez, Damián A. G.
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p. 265 - 276
(2019/07/12)
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- Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by FeCl3/Al2O3 and analysis of large1H NMR diastereotopic effect
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In the present study, we have carried out a condensation reaction for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-amino-N-benzylbenzamide and different aromatic aldehydes using FeCl3 catalyst supported on Al2O3. It was demonstrated that this material can be used successfully for the nucleation of quinazolinones with good to excellent yield; furthermore, the FeCl3/Al2O3 catalyst can be recovered and reused. This catalyst was used before in the synthesis of imidazole with very good yields. The synthesized quinazolinones showed a large range diastereotopic effect over the methylene group and, this anomalous difference was studied through nuclear magnetic resonance (NMR) and computational calculations.
- Monreal, Isabel,Sánchez-Castellanos, Mariano,Ramírez-Gualito, Karla,Cuevas, Gabriel,Espinoza, Karla A.,Rivero, Ignacio A.
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p. 124 - 131
(2018/12/13)
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- Stable iridium(iv) complexes supported by tetradentate salen ligands. Synthesis, structures and reactivity
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A series of trans-dichloroiridium(iv)-salen complexes were synthesized and structurally characterized by spectroscopic means and X-ray crystal structures. These Ir(iv) complexes are able to catalyze intramolecular C-H amination of aryl azides. The catalytic amination was drastically accelerated under microwave-assisted conditions, and possibly involves Ir-imido intermediates as supported by high-resolution ESI-MS analysis.
- Lee, Chi Lun,Wu, Liangliang,Huang, Jie-Sheng,Che, Chi-Ming
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supporting information
p. 3606 - 3609
(2019/03/26)
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- A three-component process for the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives using nanosized nickel aluminate spinel crystals as highly efficient catalysts
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NiAl2O4 spinel nanocrystals were synthesized as mesoporous catalysts and were fully characterized using Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and Energy-dispersive X-ray spectroscopy (EDS). These nanocrystals catalyzed the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via a one-pot, three-component condensation reaction of aromatic aldehydes, isatoic anhydride, and ammonium acetate or primary aromatic amine under microwave irradiation. By far, the most obvious advantages of the offered process are efficiency and recyclability of the catalyst as well as a significantly shorter reaction time.
- Safaei-Ghomi, Javad,Teymuri, Raheleh
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- 2,3-dihydro-4(1H)-quinazolinone compound as well as medicine composition and application thereof
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The invention relates to a 2,3-dihydro-4(1H)-quinazolinone compound as well as a medicine composition and application thereof. The 2,3-dihydro-4(1H)-quinazolinone compound has the main technical scheme that the structural general formula of the 2,3-dihydro-4(1H)-quinazolinone compound is shown as the formula (I) in the description; R1 is one of the following groups of hydrogen, methyl, methoxyl and halogen; R2 is one of the following groups of phenyl, a first group obtained by substituting at least one hydrogen in the phenyl by a substituent group, a pyridine group, a second group obtained bysubstituting at least one hydrogen in the pyridine group by a substituent group, a thiophene group, a furan group, saturated alicyclic hydrocarbon or first chain hydrocarbon; R3 is one of the following groups of phenyl, a third group obtained by substituting at least one hydrogen in the phenyl by a substituent group, a pyridine group, a thiophene group, a furan group, saturated alicyclic hydrocarbon and second chain hydrocarbon. The quinazolinone compound is mainly designed and synthesized; the compound can be used for preparing TRPC4 inhibitors or agonists, and preparing diabetes treatment medicine.
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Paragraph 0074; 0079; 0080; 0081; 0082; 0083; 0084; 0085
(2019/04/11)
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- Synthesis and properties of 1,2-dihydro-4(3H)-quinazolinones
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We modified the preparative-scale method for the synthesis of 2-aryl 1,2-dihydro-4(3H)-quinazolinone derivatives obtained in high yields by the reaction of new and commercially available aromatic aldehydes with anthranilic acid amides. A series of quinazolinone derivatives possessing anticancer and antiparasitic activities, as well as capable of preventing the progress of neurodegenerative diseases were characterized. There are grounds for clinical trials of these substances in order to select compounds being promising for clinical application.
- Khachatryan,Belus,Misyurin,Baryshnikova,Kolotaev,Matevosyan
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p. 1044 - 1058
(2017/10/31)
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- Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy
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A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.
- Gholap, Aniket V. A.,Maity, Soham,Schulzke, Carola,Maiti, Debabrata,Kapdi, Anant R.
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p. 7140 - 7146
(2017/09/07)
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- Crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes: A bio-nanoreactor with extremely high activity toward click-multi-component reactions
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In the present study, we have designed a procedure for the synthesis of a bio-nanoreactor catalyst, crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes (CS NPs/MWCNT@Fe3O4), via an in situ ionotropic gelation method. The synthesized robust nanoreactor was fully characterized. Moreover, the catalytic activity was investigated towards the click-based multi-component reactions for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, trisubstituted imidazoles, and 1,2,3-triazoles in a green medium. Since the nanocatalyst can be recovered by applying an external magnetic field, which results in easy separation without filtration, and recycled several times without the loss of its significant activities, it shows admirable potential in reusable catalysis.
- Shaabani, Ahmad,Afshari, Ronak,Hooshmand, Seyyed Emad
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p. 8469 - 8481
(2017/08/14)
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- Sulfated polyborate: mild, efficient and eco-friendly catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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Abstract: An efficient, inexpensive and recyclable sulfated polyborate catalyst was applied in a three-component, one-pot cyclocondensation of isatoic anhydride, aldehydes and ammonium acetate/amines to afford the corresponding 2,3-dihydroquinazolin-4(1H)-ones. The key advantages of the present method are high yields, short reaction time, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards. Graphical Abstract: [Figure not available: see fulltext.].
- Khatri, Chetan K.,Patil, Manisha S.,Chaturbhuj, Ganesh U.
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p. 1683 - 1689
(2017/06/27)
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- Reaction of benzyl alcohols, isatoic anhydride, and primary amines mediated by I2/K2CO3 in water: A new and green approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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An efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones proceeding via a three-component reaction between benzyl alcohols, isatoic anhydride, and primary amines in the presence of iodine and potassium carbonate is reported. This protocol allows the straightforward preparation of the titled products using readily available benzyl alcohols instead of unstable aldehydes under mild oxidative conditions.
- Azimi, Seyedeh Bahareh,Azizian, Javad
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p. 181 - 184
(2015/12/30)
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- One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst
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Abstract: A series of 2,3-dihydroquinazolin-4(1H)-ones have been synthesized with good to excellent yields by one-pot reaction using isatoic anhydride, aldehydes, and ammonium acetate or amines in acetonitrile in the presence of 4 ? molecular sieve modified with lanthanum(III) as an efficient heterogeneous catalyst. The catalyst could be reused without evident loss of activity. Graphical Abstract: [Figure not available: see fulltext.]
- Magyar, ágnes,Hell, Zoltán
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p. 1153 - 1162
(2016/06/01)
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- Photophysical properties of 2,3-dihydroquinazolin-4(1H)-one derivatives
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2,3-Dihydroquinazolin-4(1H)-one (DHQ) derivatives were synthesized by treatment of isatoic anhydride with amines and subsequent cyclocondensation with aldehydes or ketones. The derivatives were characterized by 1H and 13C NMR, elemental analysis and HRMS. Absorption and emission spectra of DHQ derivatives were recorded in different solvents (hexadecane, benzene, chloroform, methanol and acetonitrile). Both the absorption and the emission maxima are solvent-dependent and red-shifted. Molar extinction coefficients were determined to be 2364-4820 M-1 cm-1. The Stokes shifts of the compounds are large and increase with solvent polarity. This feature and the bathochromic effect shown for the absorption and emission processes indicate that the dipole moment of these fluorescent molecules is higher in the excited state than in the ground state. The fluorescence quantum yield and lifetime were obtained in different solvents for DHQ 4.
- Cabrera-Rivera, Fanny A.,Escalante, Jaime,Morales-Rojas, Hugo,Zigler, David F.,Schmidt, Robert D.,Jarocha, Lauren E.,Forbes, Malcolm D.E.
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- Photophysical properties of 2,3-dihydroquinazolin-4(1H)-one derivatives
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2,3-Dihydroquinazolin-4(1H)-one (DHQ) derivatives were synthesized by treatment of isatoic anhydride with amines and subsequent cyclocondensation with aldehydes or ketones. The derivatives were characterized by 1H and 13C NMR, elemental analysis and HRMS. Absorption and emission spectra of DHQ derivatives were recorded in different solvents (hexadecane, benzene, chloroform, methanol and acetonitrile). Both the absorption and the emission maxima are solvent-dependent and red-shifted. Molar extinction coefficients were determined to be 2364-4820 M-1 cm-1. The Stokes shifts of the compounds are large and increase with solvent polarity. This feature and the bathochromic effect shown for the absorption and emission processes indicate that the dipole moment of these fluorescent molecules is higher in the excited state than in the ground state. The fluorescence quantum yield and lifetime were obtained in different solvents for DHQ 4.
- Cabrera-Rivera, Fanny A.,Escalante, Jaime,Morales-Rojas, Hugo,Zigler, David F.,Schmidt, Robert D.,Jarocha, Lauren E.,Forbes, Malcolm D.E.
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- One-pot synthesis of quinazolinones from anthranilamides and aldehydes via p -toluenesulfonic acid catalyzed cyclocondensation and phenyliodine diacetate mediated oxidative dehydrogenation
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A variety of 4(3H)-quinazolinones are synthesized conveniently in one pot from 2-aminobenzamides and aldehydes, via cyclization catalyzed by p-toluenesulfonic acid followed by oxidative dehydrogenation mediated by the hypervalent iodine compound phenyliodine diacetate [PhI(OAc)2, PIDA]. Highlights of the described method include the first synthesis of quinazolinones bearing an N-alkoxy substituent, a new application of phenyliodine diacetate as an efficient dehydrogenative oxidant, and mild reaction conditions. Georg Thieme Verlag Stuttgart, New York.
- Cheng, Ran,Guo, Tianjian,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 2998 - 3006
(2013/11/06)
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- Direct halogenation reactions in 2,3-dihydro-4(1H)-quinazolinones
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Reaction of 2,3-dihydro-4(1H)-quinazolinones with NBS, Br 2/Et3N and NCS yields 6,8-Br/Cl-2,3-dihydro-4(1H)- quinazolinones with moderate to good yield. The method does not require a catalyst and offers extremely short reaction time.
- Cabrera-Rivera, Fanny A.,Ortiz-Nava, Claudia,Roman-Bravo, Perla,Escalante, Jaime,Leyva, Marco A.
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p. 2173 - 2195,23
(2020/08/31)
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- Cyanuric chloride catalyzed mild protocol for synthesis of biologically active dihydro/spiro quinazolinones and quinazolinone-glycoconjugates
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We have developed an efficient cyanuric chloride (2,4,6-trichloro-1,3,5- triazine, TCT) catalyzed approach for the synthesis of 2,3-dihydroquinazolin- 4(1H)-one (3a-3x), 2-spiroquinazolinone (5, 7), and glycoconjugates of 2,3-dihydroquinazolin-4(1H)-one (10a, 10b) derivatives. The reaction allows rapid cyclization (8-20 min) with 10 mol % cyanuric chloride to give skeletal complexity in good to excellent yield. We believe that this novel procedure may open the door for the easy generation of new and bioactive quinazolinones.
- Sharma, Moni,Pandey, Shashi,Chauhan, Kuldeep,Sharma, Deepty,Kumar, Brijesh,Chauhan, Prem M. S.
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experimental part
p. 929 - 937
(2012/03/12)
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- Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using copper benzenesulfonate as a reusable catalyst in aqueous solution
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Copper benzenesulfonate was found to be an effective catalyst for one-pot three-component cyclocon-densation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines in aqueous solution to afford the corresponding mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones in good yields. The catalyst is reusable and could be recycled for several times without distinct decrease in its efficiency. Springer-Verlag 2011.
- Wang, Min,Zhang, Ting T.,Liang, Yan,Gao, Jing J.
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experimental part
p. 835 - 839
(2012/07/28)
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- Cation-exchange resin as an efficient hetero- Geneous catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
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Various mono- and disubstituted 2,3-dihydro-4(1H)-quinazolinones were synthesized efficiently by a one-pot three-component condensation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines using a strong acidic cation-exchange resin as the catalyst in EtOH-H2O solution. The catalyst is cheap, efficient, stable, and reusable under the reaction conditions. The novel method offers several advantages, such as excellent yields, environmentally friendly reaction media, and simple procedure.
- Wang,Zhang,Gao,Liang
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p. 897 - 902
(2013/01/15)
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- Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using aluminum methanesulfonate as a reusable catalyst
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A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H2O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism for this one-pot three components reaction was proposed. Springer Science+Business Media B.V. 2011.
- Song, Zhiguo,Liu, Lianli,Wang, Yang,Sun, Xiaohu
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experimental part
p. 1091 - 1099
(2012/09/07)
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- Strontium chloride-catalyzed one-pot synthesis of 2, 3-dihydroquinazolin- 4(1H)-ones in protic media
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A wide range of mono- and disubstituted 2, 3-dihydroquinazolin-4(1H)-ones were obtained in high yields by condensation of isatoic anhydride, aldehydes with ammonium salts or primary amines in the presence of strontium chloride in aqueous ethanol under reflux.
- Wang, Min,Zhang, Ting Ting,Liang, Yan,Gao, Jing Jing
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experimental part
p. 1423 - 1426
(2012/06/01)
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- [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source
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The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.
- Liu, Yungen,Wei, Jinhu,Che, Chi-Ming
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supporting information; experimental part
p. 6926 - 6928
(2010/11/16)
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- ON THE ISOMERIZATION OF DIALKYL INDAZOLONES TO DIHYDRO-QUINAZOLINONES
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1,2-dialkyl-3-indazolones isomerize in basic medium to dihydro-4-quinazolinones.These latter, under more drastic conditions, undergo dismutation to 4(3H)-quinazolinones and antranilamides.
- Baiocchi, Leandro,Picconi, Giuseppe
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p. 5255 - 5256
(2007/10/02)
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