Synthesis and process optimization of symmetric and unsymmetric barbiturates C5-coupled with 2,1-benzisoxazoles
Benzisoxazoles represent an important pharmacophore in medicinal chemistry. Recently, an unexpected formation of symmetric 3-substituted 2,1-benzisoxazoles through reduction of 5-(2-nitrobenzylidene)barbiturates has been described. This reductive intramolecular heterocyclization probably involves a...
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Published in | Molecular diversity Vol. 24; no. 1; pp. 155 - 166 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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01.02.2020
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Abstract | Benzisoxazoles represent an important pharmacophore in medicinal chemistry. Recently, an unexpected formation of symmetric 3-substituted 2,1-benzisoxazoles through reduction of 5-(2-nitrobenzylidene)barbiturates has been described. This reductive intramolecular heterocyclization probably involves a nitroso intermediary. To improve the previous reaction conditions, the nature of the reducing agent and additives, reaction time and solvents were evaluated. By applying the optimized conditions, several symmetric and unsymmetric barbiturates C5-coupled with 2,1-benzisoxazoles were prepared with an yield of 52–87%. From this set, seven compounds were novel and the unsymmetric nature of the (thio)barbituric acid moiety was explored. For that, the total synthesis, starting from the respective urea or thiourea, was successfully performed, and 11 thiobarbiturates, benzylidene barbiturate and thiobarbiturate precursors are described.
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AbstractList | Benzisoxazoles represent an important pharmacophore in medicinal chemistry. Recently, an unexpected formation of symmetric 3-substituted 2,1-benzisoxazoles through reduction of 5-(2-nitrobenzylidene)barbiturates has been described. This reductive intramolecular heterocyclization probably involves a nitroso intermediary. To improve the previous reaction conditions, the nature of the reducing agent and additives, reaction time and solvents were evaluated. By applying the optimized conditions, several symmetric and unsymmetric barbiturates C5-coupled with 2,1-benzisoxazoles were prepared with an yield of 52–87%. From this set, seven compounds were novel and the unsymmetric nature of the (thio)barbituric acid moiety was explored. For that, the total synthesis, starting from the respective urea or thiourea, was successfully performed, and 11 thiobarbiturates, benzylidene barbiturate and thiobarbiturate precursors are described.
Graphical abstract Benzisoxazoles represent an important pharmacophore in medicinal chemistry. Recently, an unexpected formation of symmetric 3-substituted 2,1-benzisoxazoles through reduction of 5-(2-nitrobenzylidene)barbiturates has been described. This reductive intramolecular heterocyclization probably involves a nitroso intermediary. To improve the previous reaction conditions, the nature of the reducing agent and additives, reaction time and solvents were evaluated. By applying the optimized conditions, several symmetric and unsymmetric barbiturates C5-coupled with 2,1-benzisoxazoles were prepared with an yield of 52-87%. From this set, seven compounds were novel and the unsymmetric nature of the (thio)barbituric acid moiety was explored. For that, the total synthesis, starting from the respective urea or thiourea, was successfully performed, and 11 thiobarbiturates, benzylidene barbiturate and thiobarbiturate precursors are described. |
Author | Boto, Renato E. F. Serrano, João L. Silvestre, Samuel Almeida, Paulo Reis, Melani A. Soeiro, Pedro F. |
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CitedBy_id | crossref_primary_10_1016_j_bioorg_2021_105221 crossref_primary_10_1038_s41598_023_40190_w crossref_primary_10_3390_molecules26216437 crossref_primary_10_1039_D0OB02608E |
Cites_doi | 10.1016/j.crci.2017.10.002 10.1039/C8CC02364F 10.1515/HC.2007.13.4.229 10.1515/znb-2011-1201 10.1039/C6RA09874F 10.1002/ejoc.201200984 10.1080/00397919708007070 10.1016/j.tetlet.2016.11.082 10.1016/j.ejmech.2017.11.070 10.1007/s11030-015-9627-x 10.1021/ja960152n 10.1021/ol301009d 10.2174/1381612822666160224142648 10.1021/acs.orglett.7b03556 10.1016/j.tetlet.2018.06.006 10.1002/asia.201800620 10.1016/j.ejmech.2017.11.006 10.1002/adsc.201800868 10.1002/aoc.3933 10.1039/C6CE01324D 10.1002/cber.188201502147 10.1007/s10593-014-1517-0 10.2174/157017909789108701 10.1039/C7MD00449D 10.1016/j.ejmech.2018.12.059 10.1016/j.ultsonch.2016.10.010 10.1021/jo035596y 10.1007/s10593-018-2260-8 10.1007/s10593-016-1908-5 10.1016/j.tetlet.2010.11.010 10.1002/jhet.5570170625 10.1002/anie.201811177 10.1039/CT9079101330 10.1248/yakushi1947.97.8_906 |
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Keywords | 2,1-Benzisoxazoles Anthranils Process optimization Barbituric acid derivatives Nitroaromatic reduction |
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References | Ramisetti, Pandey, Lee, Karelia, Narayan, Amin, Sharma (CR28) 2018; 143 Mohammadi, Zolfigol, Khazaei, Yarie, Ansari, Azizian, Khosravi (CR33) 2018; 32 Wang, Zhao, Xi (CR29) 2011; 52 Shaker Raafat, Ishak Esam (CR4) 2011; 66 Ma, Zhou, Zhang, Jiao, Mei, Shi (CR11) 2018; 13 Mei, Shi (CR12) 2018; 54 Bordwell, Liu (CR23) 1996; 118 Wiȩcław, Bobin, Kwast, Bujok, Wróbel, Wojciechowski (CR17) 2015; 19 Krüger (CR21) 2013; 6 Gonçalves, Davi, Rockenbach, das Neves, Kagami, Canto, Figueiró, Battastini, Eifler-Lima (CR30) 2018; 59 CR34 Budruev, Dzhons (CR19) 2016; 52 Lin, Lang (CR25) 1980; 17 Ma, Jiang, Sheng, Jiao, Mei, Shi (CR9) 2018 Serrano, Cavalheiro, Barroso, Romão, Silvestre, Almeida (CR16) 2017; 20 Koshti, Thorat, Gote, Chikkali, Gonnade (CR32) 2016; 18 Keerthi Krishnan, Ujwaldev, Saranya, Anilkumar, Beller (CR8) 2019; 361 CR2 Whiteley (CR27) 1907; 91 Jorge, Rui, Samuel (CR13) 2009; 6 Singh, Sharma (CR31) 2017; 58 Banerjee (CR1) 2017; 35 Varvounis, Gerontitis, Gkalpinos (CR10) 2018; 54 Ren, Pan, Jin, Yao (CR22) 1997; 27 Ling, Maier, Das, Budhraja, Bassett, Potts, Shelat, Rankovic, Opferman, Rivas (CR7) 2019; 164 Padiya, Gavade, Kardile, Tiwari, Bajare, Mane, Gaware, Varghese, Harel, Kurhade (CR26) 2012; 14 Lopez-Munoz, Ucha-Udabe, Alamo (CR6) 2005; 1 Mohammadi Ziarani, Aleali, Lashgari (CR5) 2016; 6 Yoshikazu (CR14) 2016; 22 Figueiredo, Serrano, Cavalheiro, Keurulainen, Yli-Kauhaluoma, Moreira, Ferreira, Domingues, Silvestre, Almeida (CR3) 2018; 143 Manick, Berhal, Prestat (CR35) 2018; 20 Botsi, Tsolomitis (CR36) 2007; 13 Kotov, Prokaznikov, Antonova, Rusakov (CR20) 2014; 50 Wurz, Charette (CR24) 2004; 69 Rakesh, Shantharam, Sridhara, Manukumar, Qin (CR15) 2017; 8 Friedländer, Henriques (CR18) 1882; 15 G Mohammadi Ziarani (9937_CR5) 2016; 6 VS Koshti (9937_CR32) 2016; 18 K Keerthi Krishnan (9937_CR8) 2019; 361 AD Kotov (9937_CR20) 2014; 50 P-D Ren (9937_CR22) 1997; 27 9937_CR2 JL Serrano (9937_CR16) 2017; 20 AV Budruev (9937_CR19) 2016; 52 K Singh (9937_CR31) 2017; 58 M Shaker Raafat (9937_CR4) 2011; 66 G-J Mei (9937_CR12) 2018; 54 9937_CR34 J Figueiredo (9937_CR3) 2018; 143 SR Ramisetti (9937_CR28) 2018; 143 C Ma (9937_CR11) 2018; 13 F Lopez-Munoz (9937_CR6) 2005; 1 B Banerjee (9937_CR1) 2017; 35 M Wiȩcław (9937_CR17) 2015; 19 FG Bordwell (9937_CR23) 1996; 118 P Friedländer (9937_CR18) 1882; 15 G Varvounis (9937_CR10) 2018; 54 F Wang (9937_CR29) 2011; 52 RP Wurz (9937_CR24) 2004; 69 KJ Padiya (9937_CR26) 2012; 14 S Krüger (9937_CR21) 2013; 6 IL Gonçalves (9937_CR30) 2018; 59 Y-I Lin (9937_CR25) 1980; 17 A-D Manick (9937_CR35) 2018; 20 ARS Jorge (9937_CR13) 2009; 6 S Botsi (9937_CR36) 2007; 13 T Ling (9937_CR7) 2019; 164 C Ma (9937_CR9) 2018 U Yoshikazu (9937_CR14) 2016; 22 KP Rakesh (9937_CR15) 2017; 8 MA Whiteley (9937_CR27) 1907; 91 L Mohammadi (9937_CR33) 2018; 32 |
References_xml | – volume: 20 start-page: 990 issue: 11 year: 2017 end-page: 995 ident: CR16 article-title: A synthetic route to novel 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio)barbiturates publication-title: CR Chim doi: 10.1016/j.crci.2017.10.002 contributor: fullname: Almeida – volume: 54 start-page: 6607 issue: 50 year: 2018 end-page: 6621 ident: CR12 article-title: Catalytic asymmetric synthesis of spirooxindoles: recent developments publication-title: Chem Commun doi: 10.1039/C8CC02364F contributor: fullname: Shi – volume: 13 start-page: 229 issue: 4 year: 2007 end-page: 234 ident: CR36 article-title: One or two step acid mediated cyclocondensation process for the preparation of 5-carbethoxy-2-thiouracils from diethyl ethoxymethylenemalonate and thioureas publication-title: Heterocycl Commun doi: 10.1515/HC.2007.13.4.229 contributor: fullname: Tsolomitis – volume: 66 start-page: 1189 issue: 12 year: 2011 end-page: 1201 ident: CR4 article-title: Barbituric acid utility in multi-component reactions publication-title: Z Naturforsch B doi: 10.1515/znb-2011-1201 contributor: fullname: Ishak Esam – volume: 6 start-page: 50895 issue: 56 year: 2016 end-page: 50922 ident: CR5 article-title: Recent applications of barbituric acid in multicomponent reactions publication-title: RSC Adv doi: 10.1039/C6RA09874F contributor: fullname: Lashgari – volume: 6 start-page: 1158 year: 2013 end-page: 1169 ident: CR21 article-title: Meier C (2013) Synthesis of site-specific damaged DNA strands by 8-(acetylarylamino)-2′-deoxyguanosine adducts and effects on various DNA polymerases publication-title: Eur J Org Chem doi: 10.1002/ejoc.201200984 contributor: fullname: Krüger – volume: 1 start-page: 329 issue: 4 year: 2005 end-page: 343 ident: CR6 article-title: The history of barbiturates a century after their clinical introduction publication-title: Neuropsych Dis Treat contributor: fullname: Alamo – ident: CR2 – volume: 27 start-page: 3497 issue: 20 year: 1997 end-page: 3503 ident: CR22 article-title: Reduction of nitroarenes to n-arylhydroxylamines with KBH /BiCl system publication-title: Synth Commun doi: 10.1080/00397919708007070 contributor: fullname: Yao – volume: 58 start-page: 197 issue: 3 year: 2017 end-page: 201 ident: CR31 article-title: An isocyanide based multi-component reaction under catalyst- and solvent-free conditions for the synthesis of unsymmetrical thioureas publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2016.11.082 contributor: fullname: Sharma – volume: 143 start-page: 829 year: 2018 end-page: 842 ident: CR3 article-title: Trisubstituted barbiturates and thiobarbiturates: synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2017.11.070 contributor: fullname: Almeida – volume: 19 start-page: 807 issue: 4 year: 2015 end-page: 816 ident: CR17 article-title: General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C–H acids in aprotic media promoted by combination of strong bases and silylating agents publication-title: Mol Divers doi: 10.1007/s11030-015-9627-x contributor: fullname: Wojciechowski – volume: 118 start-page: 8777 issue: 37 year: 1996 end-page: 8781 ident: CR23 article-title: Equilibrium acidities and homolytic bond dissociation energies of N–H and/or O–H bonds in -phenylhydroxylamine and its derivatives publication-title: J Am Chem Soc doi: 10.1021/ja960152n contributor: fullname: Liu – volume: 14 start-page: 2814 issue: 11 year: 2012 end-page: 2817 ident: CR26 article-title: Unprecedented “in water” imidazole carbonylation: paradigm shift for preparation of urea and carbamate publication-title: Org Lett doi: 10.1021/ol301009d contributor: fullname: Kurhade – volume: 22 start-page: 3201 issue: 21 year: 2016 end-page: 3211 ident: CR14 article-title: 1,2-Benzisoxazole: a privileged structure with a potential for polypharmacology publication-title: Curr Pharm Des doi: 10.2174/1381612822666160224142648 contributor: fullname: Yoshikazu – volume: 20 start-page: 194 issue: 1 year: 2018 end-page: 197 ident: CR35 article-title: Development of a one-pot four C–C bond-forming sequence based on palladium/ruthenium tandem catalysis publication-title: Org Lett doi: 10.1021/acs.orglett.7b03556 contributor: fullname: Prestat – volume: 59 start-page: 2759 issue: 28 year: 2018 end-page: 2762 ident: CR30 article-title: Versatility of the Biginelli reaction: synthesis of new biphenyl dihydropyrimidin-2-thiones using different ketones as building blocks publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2018.06.006 contributor: fullname: Eifler-Lima – volume: 13 start-page: 2549 issue: 17 year: 2018 end-page: 2558 ident: CR11 article-title: Synergistic-catalysis-enabled reaction of 2-indolymethanols with oxonium ylides for the construction of 3-indolyl-3-alkoxy oxindole frameworks publication-title: Chem-Asian J doi: 10.1002/asia.201800620 contributor: fullname: Shi – volume: 143 start-page: 1919 year: 2018 end-page: 1930 ident: CR28 article-title: Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2017.11.006 contributor: fullname: Sharma – volume: 361 start-page: 382 issue: 3 year: 2019 end-page: 404 ident: CR8 article-title: Recent advances and perspectives in the synthesis of heterocycles via zinc catalysis publication-title: Adv Synth Catal doi: 10.1002/adsc.201800868 contributor: fullname: Beller – volume: 32 start-page: e3933 issue: 1 year: 2018 ident: CR33 article-title: Synthesis of nanomagnetic supported thiourea–copper(I) catalyst and its application in the synthesis of triazoles and benzamides publication-title: Appl Organomet Chem doi: 10.1002/aoc.3933 contributor: fullname: Khosravi – volume: 18 start-page: 7078 issue: 37 year: 2016 end-page: 7094 ident: CR32 article-title: The impact of modular substitution on crystal packing: the tale of two ureas publication-title: Cryst Eng Commun doi: 10.1039/C6CE01324D contributor: fullname: Gonnade – volume: 15 start-page: 2105 issue: 2 year: 1882 end-page: 2110 ident: CR18 article-title: Zur reduktion des orthonitrobenzaldehyds publication-title: Ber Dtsch Chem Ges doi: 10.1002/cber.188201502147 contributor: fullname: Henriques – volume: 50 start-page: 647 issue: 5 year: 2014 end-page: 657 ident: CR20 article-title: Synthesis of nitrogen-containing heterocycles from nitroarenes (minireview) publication-title: Chem Heterocycl Compd doi: 10.1007/s10593-014-1517-0 contributor: fullname: Rusakov – volume: 6 start-page: 426 issue: 4 year: 2009 end-page: 470 ident: CR13 article-title: Recent advances of bismuth(III) salts in organic chemistry: application to the synthesis of heterocycles of pharmaceutical interest publication-title: Curr Org Synth doi: 10.2174/157017909789108701 contributor: fullname: Samuel – volume: 8 start-page: 2023 issue: 11 year: 2017 end-page: 2039 ident: CR15 article-title: Benzisoxazole: a privileged scaffold for medicinal chemistry publication-title: MedChemComm doi: 10.1039/C7MD00449D contributor: fullname: Qin – volume: 164 start-page: 391 year: 2019 end-page: 398 ident: CR7 article-title: Identification of substituted 5-membered heterocyclic compounds as potential anti-leukemic agents publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2018.12.059 contributor: fullname: Rivas – volume: 35 start-page: 15 issue: (A) year: 2017 end-page: 35 ident: CR1 article-title: Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles publication-title: Ultrason Sonochem doi: 10.1016/j.ultsonch.2016.10.010 contributor: fullname: Banerjee – volume: 69 start-page: 1262 issue: 4 year: 2004 end-page: 1269 ident: CR24 article-title: An expedient and practical method for the synthesis of a diverse series of cyclopropane α-amino acids and amines publication-title: J Org Chem doi: 10.1021/jo035596y contributor: fullname: Charette – volume: 54 start-page: 249 issue: 3 year: 2018 end-page: 268 ident: CR10 article-title: Metal-catalyzed synthesis of five-membered ring -heterocycles: a recent update publication-title: Chem Heterocycl Compd doi: 10.1007/s10593-018-2260-8 contributor: fullname: Gkalpinos – ident: CR34 – volume: 52 start-page: 441 issue: 7 year: 2016 end-page: 443 ident: CR19 article-title: Synthesis of 2,1-benzisoxazoles (microreview) publication-title: Chem Heterocycl Compd doi: 10.1007/s10593-016-1908-5 contributor: fullname: Dzhons – volume: 52 start-page: 231 issue: 2 year: 2011 end-page: 235 ident: CR29 article-title: Copper-catalyzed one-pot synthesis of 2-thioxo-2, 3-dihydroquinazolin-4 (1 )-ones from ortho-bromobenzamides and isothiocyanates publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2010.11.010 contributor: fullname: Xi – volume: 17 start-page: 1273 issue: 6 year: 1980 end-page: 1275 ident: CR25 article-title: Selective reduction of nitro-heterocycles with sodium sulfide in aqueous -dioxane publication-title: J Heterocycl Chem doi: 10.1002/jhet.5570170625 contributor: fullname: Lang – year: 2018 ident: CR9 article-title: Design and catalytic asymmetric construction of axially chiral 3,3′-bisindole skeletons publication-title: Angew Chem Int Edit doi: 10.1002/anie.201811177 contributor: fullname: Shi – volume: 91 start-page: 1330 year: 1907 end-page: 1350 ident: CR27 article-title: CXXIII.—Studies in the barbituric acid series. I. 1: 3-Diphenylbarbituric acid and some coloured derivatives publication-title: J Chem Soc Trans doi: 10.1039/CT9079101330 contributor: fullname: Whiteley – volume: 13 start-page: 2549 issue: 17 year: 2018 ident: 9937_CR11 publication-title: Chem-Asian J doi: 10.1002/asia.201800620 contributor: fullname: C Ma – volume: 6 start-page: 426 issue: 4 year: 2009 ident: 9937_CR13 publication-title: Curr Org Synth doi: 10.2174/157017909789108701 contributor: fullname: ARS Jorge – ident: 9937_CR34 doi: 10.1248/yakushi1947.97.8_906 – volume: 52 start-page: 441 issue: 7 year: 2016 ident: 9937_CR19 publication-title: Chem Heterocycl Compd doi: 10.1007/s10593-016-1908-5 contributor: fullname: AV Budruev – volume: 91 start-page: 1330 year: 1907 ident: 9937_CR27 publication-title: J Chem Soc Trans doi: 10.1039/CT9079101330 contributor: fullname: MA Whiteley – volume: 6 start-page: 50895 issue: 56 year: 2016 ident: 9937_CR5 publication-title: RSC Adv doi: 10.1039/C6RA09874F contributor: fullname: G Mohammadi Ziarani – volume: 52 start-page: 231 issue: 2 year: 2011 ident: 9937_CR29 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2010.11.010 contributor: fullname: F Wang – volume: 361 start-page: 382 issue: 3 year: 2019 ident: 9937_CR8 publication-title: Adv Synth Catal doi: 10.1002/adsc.201800868 contributor: fullname: K Keerthi Krishnan – volume: 118 start-page: 8777 issue: 37 year: 1996 ident: 9937_CR23 publication-title: J Am Chem Soc doi: 10.1021/ja960152n contributor: fullname: FG Bordwell – volume: 17 start-page: 1273 issue: 6 year: 1980 ident: 9937_CR25 publication-title: J Heterocycl Chem doi: 10.1002/jhet.5570170625 contributor: fullname: Y-I Lin – volume: 15 start-page: 2105 issue: 2 year: 1882 ident: 9937_CR18 publication-title: Ber Dtsch Chem Ges doi: 10.1002/cber.188201502147 contributor: fullname: P Friedländer – volume: 6 start-page: 1158 year: 2013 ident: 9937_CR21 publication-title: Eur J Org Chem doi: 10.1002/ejoc.201200984 contributor: fullname: S Krüger – volume: 27 start-page: 3497 issue: 20 year: 1997 ident: 9937_CR22 publication-title: Synth Commun doi: 10.1080/00397919708007070 contributor: fullname: P-D Ren – volume: 54 start-page: 249 issue: 3 year: 2018 ident: 9937_CR10 publication-title: Chem Heterocycl Compd doi: 10.1007/s10593-018-2260-8 contributor: fullname: G Varvounis – volume: 14 start-page: 2814 issue: 11 year: 2012 ident: 9937_CR26 publication-title: Org Lett doi: 10.1021/ol301009d contributor: fullname: KJ Padiya – volume: 59 start-page: 2759 issue: 28 year: 2018 ident: 9937_CR30 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2018.06.006 contributor: fullname: IL Gonçalves – volume: 66 start-page: 1189 issue: 12 year: 2011 ident: 9937_CR4 publication-title: Z Naturforsch B doi: 10.1515/znb-2011-1201 contributor: fullname: M Shaker Raafat – volume: 164 start-page: 391 year: 2019 ident: 9937_CR7 publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2018.12.059 contributor: fullname: T Ling – volume: 143 start-page: 829 year: 2018 ident: 9937_CR3 publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2017.11.070 contributor: fullname: J Figueiredo – volume: 35 start-page: 15 issue: (A) year: 2017 ident: 9937_CR1 publication-title: Ultrason Sonochem doi: 10.1016/j.ultsonch.2016.10.010 contributor: fullname: B Banerjee – volume: 1 start-page: 329 issue: 4 year: 2005 ident: 9937_CR6 publication-title: Neuropsych Dis Treat contributor: fullname: F Lopez-Munoz – volume: 8 start-page: 2023 issue: 11 year: 2017 ident: 9937_CR15 publication-title: MedChemComm doi: 10.1039/C7MD00449D contributor: fullname: KP Rakesh – year: 2018 ident: 9937_CR9 publication-title: Angew Chem Int Edit doi: 10.1002/anie.201811177 contributor: fullname: C Ma – volume: 22 start-page: 3201 issue: 21 year: 2016 ident: 9937_CR14 publication-title: Curr Pharm Des doi: 10.2174/1381612822666160224142648 contributor: fullname: U Yoshikazu – volume: 20 start-page: 990 issue: 11 year: 2017 ident: 9937_CR16 publication-title: CR Chim doi: 10.1016/j.crci.2017.10.002 contributor: fullname: JL Serrano – volume: 19 start-page: 807 issue: 4 year: 2015 ident: 9937_CR17 publication-title: Mol Divers doi: 10.1007/s11030-015-9627-x contributor: fullname: M Wiȩcław – volume: 50 start-page: 647 issue: 5 year: 2014 ident: 9937_CR20 publication-title: Chem Heterocycl Compd doi: 10.1007/s10593-014-1517-0 contributor: fullname: AD Kotov – volume: 58 start-page: 197 issue: 3 year: 2017 ident: 9937_CR31 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2016.11.082 contributor: fullname: K Singh – volume: 20 start-page: 194 issue: 1 year: 2018 ident: 9937_CR35 publication-title: Org Lett doi: 10.1021/acs.orglett.7b03556 contributor: fullname: A-D Manick – volume: 13 start-page: 229 issue: 4 year: 2007 ident: 9937_CR36 publication-title: Heterocycl Commun doi: 10.1515/HC.2007.13.4.229 contributor: fullname: S Botsi – volume: 54 start-page: 6607 issue: 50 year: 2018 ident: 9937_CR12 publication-title: Chem Commun doi: 10.1039/C8CC02364F contributor: fullname: G-J Mei – ident: 9937_CR2 – volume: 18 start-page: 7078 issue: 37 year: 2016 ident: 9937_CR32 publication-title: Cryst Eng Commun doi: 10.1039/C6CE01324D contributor: fullname: VS Koshti – volume: 32 start-page: e3933 issue: 1 year: 2018 ident: 9937_CR33 publication-title: Appl Organomet Chem doi: 10.1002/aoc.3933 contributor: fullname: L Mohammadi – volume: 143 start-page: 1919 year: 2018 ident: 9937_CR28 publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2017.11.006 contributor: fullname: SR Ramisetti – volume: 69 start-page: 1262 issue: 4 year: 2004 ident: 9937_CR24 publication-title: J Org Chem doi: 10.1021/jo035596y contributor: fullname: RP Wurz |
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Title | Synthesis and process optimization of symmetric and unsymmetric barbiturates C5-coupled with 2,1-benzisoxazoles |
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