- Synthesis, crystal structure, vibrational properties and DFT studies of 4-(furan-2-ylmethyl)-1-(thiomorpholinomethyl)-[1,2,4]triazolo[4,3-a]quinazon-5(4H)-one
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In this present research, the title compound 4-(furan-2-ylmethyl)-1-(thiomorpholinomethyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one(1) was synthesized, and its single crystal was produced in acetone. The use of 1H NMR, 13C NMR, FT-
- Chai, Huifang,Deng, Liyuan,Hu, Weiyin,Liao, Tianhui,Liao, Weike,Sun, Hong,Zhao, Chunshen
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- UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides
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A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.
- Deng, Wei,Kambe, Nobuaki,Qiu, Renhua,Tang, Niu,Xiang, Jiannan,Yang, Tianbao,Yin, Shuang-Feng,Zeng, Dishu
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supporting information
(2022/03/17)
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- Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
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Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
- Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
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supporting information
p. 5435 - 5441
(2020/08/03)
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- Synthesis, Evaluation and Proposed Binding Pose of Substituted Spiro-Oxindole Dihydroquinazolinones as IRAP Inhibitors
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Insulin-regulated aminopeptidase (IRAP) is a new potential macromolecular target for drugs aimed for treatment of cognitive disorders. Inhibition of IRAP by angiotensin IV (Ang IV) improves the memory and learning in rats. The majority of the known IRAP inhibitors are peptidic in character and suffer from poor pharmacokinetic properties. Herein, we present a series of small non-peptide IRAP inhibitors derived from a spiro-oxindole dihydroquinazolinone screening hit (pIC50 5.8). The compounds were synthesized either by a simple microwave (MW)-promoted three-component reaction, or by a two-step one-pot procedure. For decoration of the oxindole ring system, rapid MW-assisted Suzuki-Miyaura cross-couplings (1 min) were performed. A small improvement of potency (pIC50 6.6 for the most potent compound) and an increased solubility could be achieved. As deduced from computational modelling and MD simulations it is proposed that the S-configuration of the spiro-oxindole dihydroquinazolinones accounts for the inhibition of IRAP.
- ?qvist, Johan,Agalo, Faith,Engen, Karin,Gutiérrez-de-Terán, Hugo,Hallberg, Mathias,Jensen, Annika Jenmalm,Konda, Vivek,Larhed, Mats,Lundb?ck, Thomas,Rosenstr?m, Ulrika,Vanga, Sudarsana Reddy
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p. 325 - 337
(2020/04/07)
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- A O-aminobenzoyl amine plant growth regulator (by machine translation)
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The invention discloses an anthranilic acid amides, structure such as shown in formula I: In the formula R is: The compounds and salts thereof and has very good plant growth regulating activity, spraying through the leaf area of the root and has remarka
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Paragraph 0023; 0029-0031
(2018/11/10)
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- Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
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An efficient, practical approach to the copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-one derivatives is described. The preparation involves treatment of benzyl amines with benzyl anthranilamides in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide (TBAB).
- Foroumadi, Parham,Lotfi, Vahid,Mahdavi, Mohammad,Moghimi, Setareh,Soheilizad, Mehdi,Kianmehr, Ebrahim,Firoozpour, Loghman,Asadipour, Ali,Foroumadi, Alireza
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p. 267 - 271
(2018/10/15)
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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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- An efficient metal-free synthesis of 2-amino-substituted-4(3H)-quinazolinones
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2-Amino-substituted-4(3H)-quinazolinones have been synthesized via an efficient metal-free reaction between 2-aminobenzamide derivatives and carbonimidic dibromides. The reaction proceeds in the presence of K2CO3 affording cyclized products in good to excellent yields.
- Mirza, Behrooz
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p. 146 - 147
(2015/12/23)
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- CuBr/Et3N-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-ones
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A series of novel quinazolin-4(3H)-one derivatives were efficiently synthesized starting from isatoic anhydride. First, reaction of isatoic anhydride and amines in H2O at room temperature afforded 2-aminobenzamides. Then, CuBr/Et3N promoted reaction of 2-aminobenzamides and different aryl isothiocyanates in DMF at 80° afforded the title compounds in good yield.
- Mahdavi, Mohammad,Asadi, Mehdi,Khoshbakht, Mahsa,Saeedi, Mina,Bayat, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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p. 378 - 383
(2016/06/01)
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- LOW MOLECULAR WEIGHT THYROID STIMULATING HORMONE RECEPTOR (TSHR) AGONISTS
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PROBLEM TO BE SOLVED: To provide oxo-hydroquinazolines that are useful as selective thyroid stimulating hormone receptor (TSHR) agonists and may be used for detecting or treating thyroid cancer, or treating a bone degenerative disorder. SOLUTION: The present invention provides compounds represented by a formula in the figure. [R1-R4 are each independently H, hydroxyl or the like; R5 is -CH2-Ph; A is -N=C(R15)- (where a bond at the left end bonds to the benzene ring in the formula and a bond at the right end bonds to the nitrogen heteroatom in the formula) or the like; and R15 is phenyl having specific substituents.] COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0085; 0086; 0087
(2018/09/25)
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- Synthesis of furyl-, furylvinyl-, thienyl-, pyrrolinylquinazolines and isoindolo[2,1-a]quinazolines
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A method for the synthesis of hydrogenated furyl-, furylvinyl-, thienyl-, and pyrrolinyl-substituted quinazolin-4-ones was developed. A possibility of the reaction of 2-furylquinazolines with maleic anhydride was demonstrated. A number of quinazolines obtained were subjected to a primary bioscreening on inhibition of acetylcholinesterase.
- Zaytsev,Revutskaya,Ku?menko,Novikov,Zubkov,Sorokina,Nikitina,Toze,Varlamov
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p. 1345 - 1353
(2016/03/08)
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- Solvent-free synthesis of novel benzodiazepine derivatives by a three-component base-catalysed reaction of isatoic anhydride, a primary amine and chloroacetyl chloride
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Heating isatoic anhydride with a series of primary amines at 150 °C under solvent-free conditions yielded 2-amino-N-alkylbenzamides which, in the same pot, reacted readily with chloroacetyl chloride in the presence of poly(dimethylaminoethyl acrylamide)-modified magnetic nanoparticles (MNP@PDMA), a base catalyst, to give 4-alkyl-1,4-benzodiazepine-2,5-diones in good yields without formation of by-products.
- Seydey, Mohsen Khalilpour,Rezaei, Zahra,Homami, Seyed Saied
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p. 286 - 288
(2015/06/02)
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- Novel 1,2,3,4-Tetrahydroquinazolinones via Reaction of 2-Amino-N-substituted Benzamides and Dimethyl Acetylenedicarboxylate
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Reaction of 2-amino-N-substituted benzamides and dimethyl acetylenedicarboxylate (DMAD) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in H2O at room temperature led to the formation of novel 1,2,3,4-tetrahydroquinazolinones.
- Nahavandian, Semiramis,Allameh, Sadegh,Saeedi, Mina,Ansari, Shirin,Mahdavi, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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p. 1028 - 1033
(2015/11/23)
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- MODULATORS OF THE RELAXIN RECEPTOR 1
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Disclosed are modulators of the human relaxin receptor 1, for example, of formula (I), wherein A, R1, and R2 are as defined herein, that are useful in treating mammalian relaxin receptor 1 mediated facets of human health, e.g., cardi
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Paragraph 0307-0308
(2015/05/05)
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- Synthesis of novel benzo[6,7][1,4]oxazepino[4,5-a]quinazolinone derivatives via transition-metal-free intramolecular hydroamination
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Novel benzo[6,7][1,4]oxazepino[4,5-a]quinazolinone derivatives were synthesized through an efficient 7-exo-dig hydroamination of 3-substituted-2-[2-(prop-2-yn-1-yloxy)phenyl]-2,3-dihydroquinazolin-4(1H)-ones in the presence of potassium tert-butoxide (KOt-Bu) in DMF at 130 °C. Georg Thieme Verlag Stuttgart. New York.
- Mahdavi, Mohammad,Foroughi, Niloufar,Saeedi, Mina,Karimi, Maryam,Alinezhad, Heshmatollah,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 385 - 388
(2014/03/21)
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- Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives
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A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]
- Asadi, Mehdi,Masoomi, Shiva,Ebrahimi, Seyed Mostafa,Mahdavi, Mohammad,Saeedi, Mina,Shafiee, Abbas,Foroumadi, Alireza
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p. 497 - 504
(2014/03/21)
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- Novel four-step synthesis of thioxo-quinazolino[3,4- A ]quinazolinone derivatives
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A novel synthesis of thioxo-quinazolino[3,4-a]quinazolinone framework was developed through a four-step reaction starting from isatoic anhydride. The resulting 2-aminobenzamides from the reaction of isatoic anhydride and different amines underwent coupling-cyclization reaction with 2-nitrobenzaldehydes, reduction of nitro group, and then cyclization reaction with carbon disulfide (CS2). All steps were carried out under easy and user-friendly conditions in a short time without using expensive catalysts or reagents. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Shafii, Behnaz,Saeedi, Mina,Mahdavi, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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supporting information
p. 215 - 221
(2013/12/04)
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- One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion
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An efficient and practical two-step process has been developed for the synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion in one pot. This regioselective procedure could construct a wide range of 2-amino-4(3H)- quinazolinones in moderate to excellent yields. Furthermore, the methodology also had distinct advantages of easily accessible starting materials and operational simplicity. the Partner Organisations 2014.
- Ji, Fei,Lv, Mei-Fang,Yi, Wen-Bin,Cai, Chun
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p. 5766 - 5772
(2014/07/22)
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- Reaction of isatoic anhydride, amine, and N,N′-dialkyl carbodiimides under solvent-free conditions: New and efficient synthesis of 3-alkyl-2-(alkylamino) quinazolin-4(3H)-ones
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Heating a mixture of isatoic anhydride, amines, and N,N′-dialkyl carbodiimides under solvent-free conditions provided novel 3-alkyl-2- (alkylamino)quinazolin-4(3H)-one derivatives for the first time. The products were obtained in moderate to good yields without formation of any by-products. Copyright
- Asadi, Mehdi,Ebrahimi, Mostafa,Mahdavi, Mohammad,Saeedi, Mina,Ranjbar, Parviz Rashidi,Yazdani, Farshad,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 2385 - 2392
(2013/07/26)
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- Green synthesis of new boron-containing quinazolines: Preparation of benzo[d][1,3,2]diazaborinin-4(1H)-one derivatives
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A series of new boron-containing quinazolinones, benzo[d][1,3,2] diazaborinin-4(1H)-one derivatives, were synthesized by the sequential one-pot reaction of isatoic anhydride, amines, and arylboronic acids in the absence of a catalyst and solvent. Heating isotoic anhydride and amines led to the formation of 2-aminobenzamide intermediates, which reacted easily with boronic acids to obtain the title compounds in good yields. Solvent-free conditions provided a unique procedure because the corresponding products were not obtained using various solvents either under reflux conditions or at room temperature.
- Mahdavi, Mohammad,Asadi, Mehdi,Saeedi, Mina,Tehrani, Maryam Hosseinpour,Mirfazli, Seyedeh Sara,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 2936 - 2942
(2013/09/02)
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- Synthesis of novel 1,4-benzodiazepine-3,5-dione derivatives: Reaction of 2-aminobenzamides under bargellini reaction conditions
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In this paper, we report on a user-friendly synthesis of 1,4-benzodiazepine-3,5-dione derivatives via Bargellini-type reaction. The corresponding products were obtained using various 2-aminobenzamides under Bargellini reaction conditions, in good yields without unfavorable side reaction.
- Mahdavi, Mohammad,Saeedi, Mina,Rezaei, Zahra,Foroumadi, Alireza,Shafiee, Abbas,Asadi, Mehdi,Moghbel, Hooman
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p. 2521 - 2525,5
(2012/12/11)
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- LOW MOLECULAR WEIGHT THYROID STIMULATING HORMONE RECEPTOR (TSHR) AGONISTS
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Disclosed are oxo-hydroquinazolines that are useful as selective TSHR agonists. The compounds may be used for detecting or treating thyroid cancer, or treating a bone degenerative disorder.
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- INVERSE AGONISTS AND NEUTRAL ANTAGONISTS FOR THE TSH RECEPTOR
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TSHR inverse agonists and neutral antagonists that are useful for treating Graves' orbitopathy, Graves' hyperthyroidism and/or thyroid cancer.
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Page/Page column 51
(2011/10/31)
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- Furan ring opening-pyrrole ring closure: A new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines
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A method of synthesis of pyrrolo[1,2-a][1,4]benzodiazepines is described. This method is based on the recyclization of N-(furfuryl)anthranilamides under treatment with an aq. HCl/AcOH system and allows one to form both diazepine and pyrrole rings in one step. The reaction proceeds via furan ring opening into a diketone moiety followed by consecutive interaction of the NH2-group with both carbonyl functions. The process is not efficient in the presence of alkyl or aryl groups on amide nitrogen due to competitive furfuryl cation elimination. But alkylation of pyrrolo[1,2-a][1,4]benzodiazepines yields efficiently the corresponding N-alkyl derivatives. Steric effects also prevent cyclization due to reversibility of diazepine ring formation under these reaction conditions. However, the corresponding pyrrolo[1,2-a][1,4] benzodiazepines can be obtained by a stepwise process, i.e., 1) furan ring opening with aq. HCl/AcOH and 2) cyclization of isolated aminodiketones under treatment with glacial acetic acid. Another efficient procedure for the synthesis of pyrrolo[1,2-a][1,4]benzodiazepines consists of acid-catalyzed furan ring opening of N-(furfuryl)-2-nitrobenzamides followed by treatment of the formed nitrodiketone with Fe/AcOH. It leads to a one pot reduction of nitro group to amine, cyclization into diazepine and pyrrole ring formation. This procedure is efficient both for substrates with steric demands and for N-alkyl- or N-aryl-N-(furfuryl)amides. The proposed approach can be also applied to the synthesis of parent pyrrolo[1,2-a][1,4]diazepines or their analogues annulated to heterocycles. The Royal Society of Chemistry 2010.
- Butin, Alexander V.,Nevolina, Tatyana A.,Shcherbinin, Vitaly A.,Trushkov, Igor V.,Cheshkov, Dmitry A.,Krapivin, Gennady D.
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supporting information; experimental part
p. 3316 - 3327
(2010/08/21)
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- LOW MOLECULAR WEIGHT THYROID STIMULATING HORMONE RECEPTOR (TSHR) AGONISTS
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Disclosed are oxo-hydroquinazolines of formula I that are useful as selective TSHR agonists. The compounds may be used for detecting or treating thyroid cancer, or treating a bone degenerative disorder.
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Page/Page column 24
(2010/05/13)
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- Hydrolytic opening of the quinazoline ring in 3-furfuryl-4-oxo-3,4- dihydroquinazoline derivatives
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Ethyl 3-furfuryl-4-oxo-3,4-dihydroquinazoline-2-carboxylate extremely readily undergoes hydrolysis in acid, alkaline, or neutral medium with formation of 2-(2-ethoxy-1,2-dioxoethylamino)-N-furfurylbenzamide. The reaction of ethyl 3-furfuryl-4-oxo-3,4-dihy
- Shemchuk,Chernykh,Levashov,Sytnik
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experimental part
p. 1243 - 1245
(2011/02/21)
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- Synthesis and in vitro study of platelet antiaggregant activity of some 4-quinazolinone derivatives
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Some new 4-quinazolinones were prepared. Their antiplatelet activity was evaluated in vitro with respect to aggregation induced by ADP, collagen, arachidonic acid and the platelet serotonin release reaction. Most molecules showed an inhibiting power similar to that of acetylsalicylic acid under the same conditions, and even greater when aggregation was induced by ADP. Reduction of the 4-quinazolinone derivatives to their 1,2,3,4-tetrahydroquinazoline homologues produced an increase in platelet inhibitory action except when ADP is the inductor.
- Gravier,Dupin,Casadebaig,Hou,Boisseau,Bernard
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