{"title":"SbPh3: An Efficient Catalyst for Dihydropyrimidinone and Dihydropyrimidin-5-carboxamide Synthesis Using the Biginelli Reaction","authors":"Anamika Khaskel, Santosh Kumari Bajiya, Suman Lata, Rakesh K Sharma, Shatabdi Basu","doi":"10.1080/00304948.2023.2190711","DOIUrl":"https://doi.org/10.1080/00304948.2023.2190711","url":null,"abstract":"","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-04-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45073079","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of Isoxazole-5(4H)-ones Using Citrazinic Acid as an Organocatalyst in Aqueous Conditions","authors":"Hanieh Ostadzadeh, H. Kiyani","doi":"10.1080/00304948.2023.2192601","DOIUrl":"https://doi.org/10.1080/00304948.2023.2192601","url":null,"abstract":"The isoxazolone framework has been found to have a wide variety of biological properties including, antioxidant, 1 antifungal, 2 antibacterial, 3 fungicide, 4 analgesic, 5 antimicrobial, 6 anti-Alzheimer, 7 and anti-androgen 8 activities. Figure 1 shows several biologically active isoxazolones. In addition, this scaffold can be used in nonlinear optical materials, 9 filter dyes, 10 molecular devices, 11 donor-acceptor Stenhouse adducts (DASAs), 12 and solar cells. 13 In addition to biological and medical applications, isoxazolone derivatives have also been used as intermediates for the syntheses of other organic compounds. 4,14 – 17","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42404162","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Development of an Efficient Alternative Synthesis of the Endothelin Receptor Antagonist Bosentan","authors":"Jigar Panchal , Namita Misra , Meenu Devi , Ashima Sharma , Sonika Jain , Pankaj Jain , Jaya Dwivedi , Swapnil Sharma","doi":"10.1080/00304948.2023.2170665","DOIUrl":"10.1080/00304948.2023.2170665","url":null,"abstract":"Pulmonary artery hypertension (PAH), is characterized by pulmonary vascular resistance that may lead to heart failure. 1 – 2 Endothelin receptor antagonists (ERAs) have been considered as rational targets in the therapy of PAH. 3 Bosentan monohydrate (brand name Tracleer V R ) is the first orally administered drug approved by the U.S. Food and Drug Administration indicated for the therapy of PAH. 4 Bosentan (4-( tert -butyl)- N -(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2 ’ -bipyrimidin]-4-yl)benzenesulfonamide (","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 5","pages":"Pages 404-410"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49084087","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"An Original Transposition of the 4-Fluorobenzylamino Group from 1-(4-Fluorobenzylamino)-1-methylsulfanyl-2-nitroethylene in Triflic Acid†","authors":"Bamba Fante , N’ta Christelle Mélissa Ambeu-Loko , Souleymane Coulibaly , Yaya Soro , Jean-Marie Coustard","doi":"10.1080/00304948.2023.2178212","DOIUrl":"10.1080/00304948.2023.2178212","url":null,"abstract":"Bamba Fante , N’ta Christelle M elissa Ambeu-Loko, Souleymane Coulibaly , Yaya Soro, and Jean-Marie Coustard Laboratoire de Constitution et R eaction de la Mati ere, UFR SSMT, Universit e F elix Houphou€et-Boigny, Abidjan, Côte d’Ivoire; Laboratoire des Proc ed es Industriels de Synth ese et d’Environnement, Institut National Polytechnique F elix Houphou€et-Boigny, Yamoussoukro, Côte d’Ivoire; Institut de Chimie des Milieux et Mat eriaux de Poitiers, Universit e de Poitiers, Poitiers, France","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 5","pages":"Pages 411-420"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41916627","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"An Efficient Procedure for the Synthesis of 2-Arylsubstituted Benzimidazoles Catalyzed by Co (II) Immobilized on Fe3O4@SiO2-NH2/EP@SAA as a Recyclable Nanomagnetic Catalyst","authors":"Mohammad Nikbin , Ebrahim Mollashahi , Malek Taher Maghsoodlou , Mojtaba Lashkari","doi":"10.1080/00304948.2023.2181622","DOIUrl":"10.1080/00304948.2023.2181622","url":null,"abstract":"Fast, simple and high-yield synthesis continues to be a major challenge for synthetic organic chemists. Among nitrogen-containing heterocyclic compounds, 1 the benzimidazole ring is an important pharmacophore for modern drug discovery. 2 Benzimidazoles have significant biological properties including anticancer, 3 anti-HIV, 4 antibacterial, 5 anti-ulcer, 6 anti-tumor 7 and enzyme inhibitory 8 properties. Benzimidazoles are also important intermediates in organic reactions. 9 Due to the importance of benzimidazoles, interest in the synthesis of these compounds has increased. The most common method is the condensation of o -aryldiamines and carbonyl compounds, especially aldehydes; and the wide availability of the latter makes this route particularly attractive for the production of 2-arylsubstituted benzimidazoles. 10 Numerous oxidative and catalytic reagents have been employed in this method, including Oxone, 11 In(OTf) 312 , FeCl 3 (cid:1) 6H 2 O, 13 I 2 /KI/K 2 CO 314 , sulfamic acid, 15 KHSO 416 , TBAF, 17 SBSA, 18 TiCl 3 OTf 19 and VOSO 4 . 20 These catalysts have been useful for their own purposes in facilitating the synthesis of the expected compounds. However, some of these methods have disadvantages such as high reaction temperatures, prolonged reaction times, low yields, expense, complex work-up procedures or toxic solvents. So the discovery of mild","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 5","pages":"Pages 444-451"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46044612","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of Tetrahydrobenzo[b]pyrans Promoted by Sodium Stearate as a Lewis Base-Surfactant Combined Catalyst in an Aqueous Micellar Medium","authors":"Farzaneh Mohamadpour","doi":"10.1080/00304948.2022.2151812","DOIUrl":"10.1080/00304948.2022.2151812","url":null,"abstract":"The use of green catalysts is one of the most crucial elements in the greening of synthetic chemical processes. In line with this, current research initiatives in our lab have concentrated on the creation of green catalysts 1 – 4 for organic synthesis. Surfactant molecules can group together in an aqueous phase under ambient conditions to create micelles, which have a hydrophobic core and a hydrophilic corona. The widespread and in-depth study of micellar surfactants as catalysts for various reactions in aqueous solutions opens the door for more synthesis methods using aqueous media. Sodium stearate is a common surfactant found in frequently-used preparations. However, there are not many studies on organic reactions using sodium stearate as a catalyst. 5 In this context, we present below a straightforward and effective technique for the synthesis of tetrahy-drobenzo[ b ]pyrans using a Lewis base-surfactant-combined (LBSC) catalyzed three-component one-pot reaction in an aqueous micellar medium. Pyrans have such noteworthy pharmacological characteristics (Figure 1) as Chk1 kinase inhibitory, 6 analgesic, 7 anticancer, 8 vasodilatory, 9 antihypertensive, hepatoprotective, cardiotonic, 10 vasodilator, 11 anti-leukemic, 12,13 emetic, 14 anti-anaphylactic, 15 diuretic 16 and anti-Alzheimer 17 properties. Many","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 4","pages":"Pages 345-350"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41410183","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of a Novel Disubstituted Indole†","authors":"Stephen W. Wright , Gordon W. Gribble","doi":"10.1080/00304948.2023.2184622","DOIUrl":"10.1080/00304948.2023.2184622","url":null,"abstract":"In continuation of our interest to functionalize selectively the indole-2,3 positions, we now describe the synthesis of 2-bromo-1-(phenylsulfonyl)-1H-indol-3-yl trifluoromethanesulfonate (1) as a potentially useful precursor for the selective functionalization of the indole positions. Our synthesis of 1 is shown in Scheme 1. Following the conversion of commercially available 2-aminoacetophenone (2) to sulfonamide 3, the four subsequent reactions to give 1 were performed with only one intermediate purification due to the presumed formation of indigo by-products (blue-purple discoloration), and the possible lachymatory effects of bromide 4. Bromination of 3 to 4 was subject to capricious reaction times, but we found that the addition of catalytic amounts of concentrated HBr eliminated this phenomenon, presumably by supplying sufficient HBr to the mixture to initiate formation of Br2. Over-bromination of 3 was minimized by exclusion of air. The mixture of 4, containing some ketone and dibromoketone, was converted to indolin-3-one 5 in 60% yield after purification. Subsequent bromination to 6 and triflate formation to 1 proceeded in 54% yield for the two steps. Attempts to brominate (NBS, Br2) the known 1-(phenylsulfonyl)-1H-indol-3-yl trifluoromethanesulfonate to afford 1 were not successful. In summary, we disclose a straightforward synthesis of compound 1 from 2-aminoacetophenone. This new 2,3-unsymmetrically-disubstituted indole should find utility in the synthesis of a wide range of indoles in contrast to, for example, 2,3-dihaloindoles for which regioselective reactions have proven difficult.","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 5","pages":"Pages 483-486"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43934635","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Anton Mastitski , Eerold Vellemäe , Varvara Smorodina , Alar Konist , Jaak Järv
{"title":"Alcoholysis of Primary Amides in the Presence of CF3SO3H","authors":"Anton Mastitski , Eerold Vellemäe , Varvara Smorodina , Alar Konist , Jaak Järv","doi":"10.1080/00304948.2023.2184997","DOIUrl":"10.1080/00304948.2023.2184997","url":null,"abstract":"Esters have a lot of applications as fragrances, emulsifiers and solvents","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 5","pages":"Pages 458-468"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42005125","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Supramolecular β-Cyclodextrin as a Reusable Catalyst for Xanthene Synthesis in Aqueous Medium","authors":"Farzaneh Mohamadpour","doi":"10.1080/00304948.2022.2141047","DOIUrl":"10.1080/00304948.2022.2141047","url":null,"abstract":"In green chemistry, the most notable objectives include atom economy, the use of non-hazardous catalysts and solvents","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 4","pages":"Pages 317-325"},"PeriodicalIF":1.5,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48320701","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}