- Comparative biological study between quinazolinyl–triazinyl semicarbazide and thiosemicarbazide hybrid derivatives
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Abstract: Practical synthesis and biological activities of quinazolinyl–triazinyl semicarbazides (10a–j) and quinazolinyl–triazinyl thiosemicarbazides (11a–j) have been described. The novel semicarbazides and thiosemicarbazides were prepared by condensati
- Patel, Janki J.,Modh, Rahul P.,Asamdi, Manjoorahmed,Chikhalia, Kishor H.
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p. 2271 - 2287
(2020/07/04)
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- 2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: Synthesis and photophysical properties
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Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7
- Alimi, Kamel,Ayed, Mohamed Adnene Hadj,Braiek, Mourad Ben,Chaaben, Noureddine,Jabli, Mahjoub,Jopp, Stefan,Langer, Peter,Tka, Najeh
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p. 1629 - 1640
(2021/07/26)
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- Preparation method of 3,5-dibromo-2-aminobenzoic acid
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The invention discloses a preparation method of 3,5-dibromo-2-aminobenzoic acid. The preparation method comprises the following steps: (I) performing in-situ oxidation on bromide with an oxidant underan acidic condition, and carrying out a bromination reaction on phthalimide to obtain N-bromophthalimide; (II) performing Hoffmann degradation on the N-bromophthalimide under the action of alkali toobtain 2-aminobenzoic acid and bromoanion; (III) further adding an appropriate amount of bromide and oxidant, and carrying out a bromination reaction on the 2-aminobenzoic acid to obtain the product,namely, 3,5-dibromo-2-aminobenzoic acid. The preparation method has the advantages of environment-friendly reaction system, simple, convenient and safe reaction operation, low cost, high reaction selectivity and high product yield and the like.
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Paragraph 0038-0073
(2019/01/16)
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- Method of catalytically synthesizing polybromo-aniline in water phase
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The invention discloses a method of catalytically synthesizing polybromo-aniline in a water phase. The method comprises following steps: adding a catalytic amount of a free radical initiator, aniline derivatives, cheap and low-toxic bromine salts, and water into a reactor; carrying out reactions in a photocatalytic reaction instrument under power of 5W at a room temperature; after a while, extracting the reaction product by ethyl acetate, and carrying out recrystallization to obtain polybromo-aniline; wherein the free radical initiator is eosin, sodium persulfate, or potassium persulfate. The power of the incandescent lamp of the photocatalytic reaction instrument is 5W. The free radical initiator and bromine salts are cheap and easily available. The method is an ideal synthesis method of polybromo-aniline. Cheap and low-toxic bromine salts are used to replace liquid bromine. The cheap and easily available free radical initiator is used to replace unstable and explosive hydrogen peroxide. After 4 to 10 hours of reactions under the power of 5W, polybromo-aniline can be synthesized, the yield and the reaction selectivity are high, the byproducts are few, and the post treatment is simple.
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Paragraph 0012; 0023
(2019/10/04)
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- Preparation method for ambroxol hydrochloride intermediate 3,5-dibromo-2-aminobenzoic acid
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The invention discloses a preparation method for an ambroxol hydrochloride intermediate 3,5-dibromo-2-aminobenzoic acid. The method enables the ambroxol hydrochloride intermediate 3,5-dibromo-2-aminobenzoic acid to be obtained through the following two-st
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Paragraph 0021; 0032; 0033; 0035; 0039
(2019/01/14)
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- Preparation method of bromhexine hydrochloride
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The invention provides a preparation method of bromhexine hydrochloride. The method comprises the steps that 2-amino-3, 5-dibromo-benzene and N-methyl cyclohexane are used as the raw material, and bromhexine hydrochloride is obtained after reductive amina
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Paragraph 0054; 0055; 0056
(2017/08/28)
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- Insect cyclopropanecarboxamide compound and preparing method thereof and application
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The invention is insect cyclopropanecarboxamide compound and preparing method thereof and application relating to field of pesticide. The insect cyclopropanecarboxamide compound in the invention is a new compound that acts on ryanicide recipient of insect
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Paragraph 0043; 0044; 0045
(2017/08/28)
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- Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids
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The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.
- Dzhons, Daria Yu.,Budruev, Andrei V.
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supporting information
p. 874 - 881
(2016/07/06)
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- PYRAZOLYL AMIDE COMPOUNDS AND USES THEREOF
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Disclosed is a pyrazole amide compound of a novel structure as represented by general formula I, wherein, each substituent group is as defined in the specification. The compound of general formula I has good insecticidal activity, and can be used for pest control.
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Paragraph 0130-0131
(2016/10/27)
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- Efficient access to 2,6,8-trisubstituted 4-aminoquinazolines through microwave-assisted one-pot chemoselective Tris-Suzuki-Miyaura or SNAr/bis-Suzuki-Miyaura reactions in water
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An efficient, sequential, one-pot strategy for synthesizing polyfunctionalized quinazoline derivatives is presented. After selective amination of 6,8-dibromo-2,4-dichloroquinazoline at the C-4 position, 2,6,8-trisubstituted 4-aminoquinazoline derivatives
- Kabri, Youssef,Crozet, Maxime D.,Terme, Thierry,Vanelle, Patrice
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p. 3806 - 3817
(2015/06/16)
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- One-pot chemoselective synthesis of 2,4,6,8-tetrasubstituted quinazolines via microwave-assisted consecutive bis-SNAr/Bis-Suzuki-Miyaura cross-coupling reactions
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A practical and efficient synthesis of 2,4,6,8-tetrasubstituted quinazolines through one-pot chemoselective sequential bis-SNAr/bis- Suzuki-Miyaura reactions under microwave irradiation is presented. The bis-SNAr reaction occurs selectively at the C-2 and C-4 positions of 6,8-dibromo-2,4-dichloroquinazoline and the bis-Suzuki-Miyaura cross-coupling at C-6 and C-8. This procedure affords convergent synthesis of polysubstituted quinazoline derivatives in high yields in very few steps and tolerates a wide range of boronic acids and amines.
- Kabri, Youssef,Crozet, Maxime D.,Redon, Sebastien,Vanelle, Patrice
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p. 1613 - 1620
(2014/06/23)
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- Design, synthesis, antimicrobial activity and anti-HIV activity evaluation of novel hybrid quinazoline-triazine derivatives
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A series of novel hybrid quinazoline-triazine derivatives was designed and synthesized from cyanuric chloride and anthranilic acid through sequential reactions, which contain different pharmacophores like quinazoline and substituted diaryl triazine (DATA)
- Modh, Rahul P.,De Clercq, Erik,Pannecouque, Christophe,Chikhalia, Kishor H.
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p. 100 - 108
(2014/03/21)
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- Synthesis of novel quinazolinone derivatives with methyl (E)-2-(3-methoxy)acrylate moiety
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A new series of quinazolinone derivatives with methyl (E)-2-(3-methoxy) acrylate moiety have been designed and synthesized. All target compounds had been identified by 1H NMR spectrum, IR spectrum and HR-MS (high resolution mass spectrum). Three target compounds (10a, 10e, 10h) were chosen to preliminarily test the antibacterial activities, the results showed that all three target compounds exhibited antibacterial activities against three bacterial strains (Proteobacteria, Salmonella, Colibacillus).
- Dong, Kui-Kui,Zhou, Hua-Hong,Guo, A-Rong,Chen, Tian,Wang, Yu-Liang
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p. 1039 - 1042
(2013/05/08)
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- Substituents effects on activity of kynureninase from Homo sapiens and Pseudomonas fluorescens
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A series of substituted kynurenines (3-bromo-dl, 3-chloro-dl, 3-fluoro-dl, 3-methyl-dl, 5-bromo-l, 5-chloro-l, 3,5-dibromo-l and 5-bromo-3-chloro-dl) have been synthesized and tested for their substrate activity with human and Pseudomonas fluorescens kynureninase. All of the substituted kynurenines examined have substrate activity with both human as well as P. fluorescens kynureninase. For the human enzyme, 3- and 5-substituted kynurenines have k cat and kcat/Km values higher than l-kynurenine, but less than that of the physiological substrate, 3-hydroxykynurenine. However, 3,5-dibromo- and 5-bromo-3-chlorokynurenine have kcat and kcat/Km values close to that of 3-hydroxykynurenine with human kynureninase. The effects of the 3-halo substituents on the reactivity with human kynureninase may be due to electronic effects and/or halogen bonding. In contrast, for the bacterial enzyme, 3-methyl, 3-halo and 3,5-dihalokynurenines are much poorer substrates, while 3-fluoro, 5-bromo, and 5-chlorokynurenine have kcat and kcat/K m values comparable to that of its physiological substrate, l-kynurenine. Thus, 5-bromo and 5-chloro-l-kynurenine are good substrates for both human as well as bacterial enzyme, indicating that both enzymes have space for substituents in the active site near C-5. The increased activity of the 5-halokynurenines may be due to van der Waals contacts or hydrophobic effects. These results may be useful in the design of potent and/or selective inhibitors of human and bacterial kynureninase.
- Maitrani, Chandan,Phillips, Robert S.
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p. 4670 - 4677
(2013/07/26)
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- Synthesis of {2,3-dihydro-7-halopyrrolo-[(2,1-b)]-quinazolin-9-(1h)-one and 2,3-dihydro-5,7-dihalopyrrolo-[(2,1-b)]-quinazolin-9-(1h)-one}: New analogs of deoxyvasicinone
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A series of novel halogen-substituted deoxyvasicinone f2,3-dihydro-7- halopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one and 2,3-dihydro-5,7-dihalopyrrolo- [(2,1-b)]-quinazolin-9-(1H)-oneg derivatives was synthesized by condensation of halogenated anthranilic acids (2, 3, 4, 5) with 4-aminobutyric acid (6) in refluxing m-xylene over phosphorus pentoxide for 3 h to give the desired compounds (7a-7d). Taylor & Francis Group, LLC.
- Ojo, Babatunde,Chowdhury, Bejoy K.
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scheme or table
p. 1002 - 1009
(2012/02/02)
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- An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid
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A simple, efficient, and rapid method was developed for high-yielding regioselective monobromination of activated aromatic compounds using NBS in combination with ionic liquid 1-butyl-1-methylimidazolium bromide ([Bmim]Br) or dioxane. The ionic liquid is recyclable and can be reused with minimal loss in the catalytic efficiency if the ionic liquid is rapidly microwaved prior to reactions.
- Pingali, Subramanya R.K.,Madhav, Monika,Jursic, Branko S.
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experimental part
p. 1383 - 1385
(2010/04/25)
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- Effect of structural factors and solvent nature in bromination of anilines
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Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.
- Bagmanov
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experimental part
p. 1570 - 1576
(2011/06/20)
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- Synthesis and anti-microbial screening of some Schiff bases of 3-amino-6,8-dibromo-2-phenylquinazolin-4(3H)-ones
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In the present study, a series of novel Schiff bases were synthesized by condensation of 3-amino-6,8-dibromo-2-phenylquinazolin-4(3H)-ones with different aromatic aldehydes via cyclized intermediate 6,8-dibromo-2-phenyl benzoxazin-4-one. The chemical stru
- Panneerselvam, Perumal,Rather, Bilal Ahmad,Ravi Sankar Reddy, Dontireddy,Ramesh Kumar, Natesh
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scheme or table
p. 2328 - 2333
(2009/09/05)
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- Synthesis of some new substituted quinazolin-4-3H-ones as potent anticonvulsant agents
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A new series of 3-(4-(2-(6,8-dibromo-3-(substituted phenyl)-4-oxo-3,4- dihydroquinazolin-2-y1)methyl) hydrazinyl)thiazol-2-y1)-2-phenylthiazolidin-4- ones were synthesized and their structures were elucidated on the basis of elemental analyses and spectro
- Garg, Neha,Chandra, Trilok,Lata,Saxena,Kumar, Ashok
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experimental part
p. 8 - 14
(2010/09/04)
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- Oxidative bromination of aniline and its derivatives
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Oxidative bromination of aniline and its derivatives containing various substituents (CH3, Cl, NO2, COOH) in ortho, meta, and para positions with a brominating mixture of NaBr (KBr) and 20-22% hydrogen peroxide in 6-8% hydrochloric acid at the molar ratio aniline: NaBr (KBr): H 2O2: HCl = 1: 3.5: 3.2: 4.5 is described.
- Salakhov,Bagmanov,Umaeva,Bagmanova
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experimental part
p. 1479 - 1481
(2009/02/05)
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- Rapid microwave-assisted solution phase synthesis of 6,8-disubstituted 2-phenyl-3-(substituted- benzothiazol-2-yl)-4-[3H]-quinazolinones as novel anticonvulsants
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A fast and highly efficient microwave accelerated solution phase procedure for the synthesis of a series of 2-phenyl-3-(benzothiazol-2-yl)-4[3H]- quinazolinones, substituted in the benzothiazole ring, is developed. The title compounds were characterized by elemental analyses, IR, 1H NMR, and EI-MS data. The anticonvulsant activity of all the new compounds (3a-m and 4a-m) was evaluated against Maximum Electroshock (MES) induced seizures and against subcutaneous pentylenetetrazole (PTZ) induced seizures model in mice. The neurotoxicity was assessed using the Rotorod procedure. All the compounds tested were administered intraperitoneally at a various dose levels ranging from 7-200 mg/Kg body weight and the median toxic dose (TD50) and the protection index (PI) values were determined. In general compounds 3a-m were found to be more potent compared to compounds 4a-m. Among the compound tested, the compound 3e in the 2-phenyl-3-(benzothiazole-2-yl)-4[3H]-quinazolinone series and 4l in the 6,8-dibromo-2-phenyl-3-(benzothiazole-2-yl)-4[3H]-quinazolinone series were found to be the most potent. Copyright Taylor & Francis Group, LLC.
- Laddha, Sachin S.,Bhatnagar, Satyendra P.
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scheme or table
p. 2262 - 2273
(2009/07/18)
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- Regioselective aromatic electrophilic bromination with dioxane dibromide under solvent-free conditions
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Highly regioselective ring bromination of aromatic compounds has been accomplished with high yields and good purity using dioxane dibromide (DD) under solvent-free conditions. Notable features of this methodology include operational simplicity, rapid reactions, excellent control over the degree of bromination, and tolerance of various functional groups during the reaction. Copyright Taylor & Francis Group, LLC.
- Chaudhuri, Subrata Kumar,Roy, Sanchita,Saha,Bhar, Sanjay
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p. 581 - 585
(2007/10/03)
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- Synthesis and antimicrobial activities of some novel substituted 2-imidazolyl-N-(4-oxo-quinazolin-3(4H)-yl)-acetamides
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Several substituted-quinazolin-3(4H)-ones 8-11ad were synthesized by condensation of 2-chloro-N-(4-oxosubstituted-quinazolin-3(4H)-yl)-acetamides with various substituted imidazoles through one pot reaction. Elemental analysis, IR, 1H-NMR and mass spectral data confirmed the structure of the newly synthesized compounds. Synthesized quinazolin-4-one derivatives were investigated for their antitubercular, antibacterial and antifungal activities. Some of the tested compounds showed good antitubercular activity. None of the synthesized compounds showed significant antibacterial and antifungal activity.
- Raghavendra, Nulgulmnalli Manjunathiah,Thampi, Parameshwaran,Gurubasavarajaswamy, Purvarga Mattada,Sriram, Dharmarajan
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p. 1615 - 1619
(2008/09/19)
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- Synthesis and?bronchodilator activity of?new quinazolin derivative
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Taking lead from a naturally occurring quinazolin vasicine, a number of compounds were developed and evaluated for bronchodilator and anti-allergic activities. One of these compounds was 2,4-diethoxy-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-one,
- Zabeer,Bhagat,Gupta,Singh,Youssouf,Dhar,Suri,Suri,Satti,Gupta,Qazi
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p. 429 - 434
(2007/10/03)
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- REACTIONS OF 6,8-DIBROMO-2-METHYL-3,1-BENZOXAZIN-4-ONE WITH SCHIFF BASES AND AZINES
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6,8-Dibromo-2-methyl-3,1-benzoxazin-4-one (1) reacts with benzylideneaniline or p-methoxybenzylideneaniline in dry benzene to give 2-acetylamino-3,5-dibromobenzanilide (2) in both cases.When the reaction was conducted in glacial acetic acid, 6,8-dibromo-2-methyl-3-phenylquinazolin-4-one (3) was obtained.The reaction of 1 with benzalazine in glacial acetic acid yielded a mixture of 3,5-dibromoanthranilic acid (6) and 3-benzylideneamino-6,8-dibromo-2-styrylquinazolin-4-on (7) while its reaction with p-methoxybenzylideneaniline under similar conditions gave a mixture of 2-acetylamino-N-p-methoxybenzylidineamino-3,5-dibromobenzhydrazide (8) and its cyclization product, 6,8-dibromo-3-p-methoxybenzylidineamino-2-methylquinazolin-4-one (9).When the reaction of 1 with the above azines were carried out in dry benzene, a mixture of 2-acetylamino-3,5-dibromobenzhydrazide (10) and 3,5-dibromoanthranilic acid was obtained in both cases.The structure in most cases were confirmed by comparision with authentic samples and by independent syntheses of 7 and 9 by the reaction of 10 with benzaldehyde and p-methoxybenzaldehyde, respectively.
- Ismail, M. Fekry,El-Khamry, Abdel Momen A.,Abdel-Hamid, Hoda A.,Emara, Samir A.
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- BEHAVIOUR OF 2-SUBSTITUTED 6,8-DIBROMO-3,1-BENZOXAZIN-4-ONES TOWARDS o-PHENYLENEDIAMINE AND ANTHRANILIC ACID; A CASE OF UNUSUAL CLEAVAGE OF 6,8-DIBROMO-2-METHYL-3,1-BENZOXAZIN-4-ONE
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6,8-Dibromo-2-methyl-3,1-benzoxazin-4-one (1) reacts with o-phenylenediamine to give a mixture of 3,5-dibromoanthranilic acid (2), 2-methylbenzimidazole (3) and 3-(o-aminophenyl)-6,8-dibromo-2-methylquinazolin-4-one (4).However, when the reaction was conducted in ethanol or in the absence of solvent at elevated temperature, a mixture of (2) and (3) was obtained.A similar cleavage of (1) took place when it was allowed to react with anthranilic acid yielding a mixture of (2) and N-acetylanthranilic acid (6).The reaction of o-phenylenediamine with 6,8-dibromo-2-phenyl-3,1-benzoxazin-4-one (7) proceeded normally to give 3-(o-aminophenyl)-6,8-dibromo-2-phenylquinazolin-4-one (8) or 2-benzoylamino-3,5-dibromo-N-(o-aminophenyl)benzamide (9), depending upon the reaction conditions.
- Ismail, M. Fekry,El-Khamry, Abdel Momen A.,Hamid, Hoda A. Abdel,Emara, Samir A.
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p. 3757 - 3760
(2007/10/02)
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- Substitution Reactions of Phenylated Aza-Heterocycles. Part 2. Bromination of Some 2,5-Diaryl-1,3,4-oxadiazoles
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Electrophilic bromination of the title compounds may be achieved using either bromine in oleum, or bromine and potassium bromate in a sulphuric-acetic acid mixture.Under the milder reaction conditions provided by the latter, 2-(p-nitrophenyl)-5-phenyl-1,3,4-oxadiazole (2), the model compound used in this study, is mono- and di-brominated in the phenyl ring.In the first bromination step, all three monobromo-isomers are produced in appreciable amount.The orientation of the second bromination is controlled entirely by the first bromine and not by the oxadiazole substituent: this is confirmed by a separate study of the bromination of the three monobromo-compounds (3a-3c).
- Blackhall, Alexander,Brydon, Donald L.,Javaid, Khalid,Sagar, Anthony J. G.,Smith, David M.
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p. 3485 - 3497
(2007/10/02)
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- Process for the preparation of sulfur-containing N-benzyl-amino acids and esters
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A process for the preparation of sulfur-containing N-benzyl-amino acids of the formula STR1 wherein X and Y, which may be identical to or different from each other, are each hydrogen or halogen; R1 is hydrogen or alkyl of 1 to 4 carbon atoms; R2 is hydrogen, alkyl of 1 to 3 carbon atoms, carboxy-lower alkyl or acyl; R3 is hydrogen or acyl; and n is 1 or 2; which comprises the steps of converting anthranilic acid or a halogenated anthranilic acid into the corresponding aldehyde, reacting the aldehyde with a compound of the formula STR2 wherein R1, R2 and n have the meanings previously defined, to form the corresponding Schiff's base, reducing the said Schiff's base, and recovering the reaction product.
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