Giulia Antonini, Laura Petrosilli, Ilaria Giussani, Maria Gessica Ciulla, Sarah Mazzotta, Giuseppe D'Orazio
The Front Cover shows domino transformations, which play a crucial role as chemical tools in drug discovery processes. In their Review (DOI: 10.1002/ejoc.202400511), S. Mazzotta, G. D'Orazio and co-workers showcase various instances of domino transformations applied to carbohydrates, with the goal of summarizing their chemical potential in producing sugar-derived compounds. These compounds have significant applications in generating new chemical scaffolds for drug discovery and chemical biology.
{"title":"Front Cover: Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art (Eur. J. Org. Chem. 39/2024)","authors":"Giulia Antonini, Laura Petrosilli, Ilaria Giussani, Maria Gessica Ciulla, Sarah Mazzotta, Giuseppe D'Orazio","doi":"10.1002/ejoc.202483901","DOIUrl":"10.1002/ejoc.202483901","url":null,"abstract":"<p><b>The Front Cover</b> shows domino transformations, which play a crucial role as chemical tools in drug discovery processes. In their Review (DOI: 10.1002/ejoc.202400511), S. Mazzotta, G. D'Orazio and co-workers showcase various instances of domino transformations applied to carbohydrates, with the goal of summarizing their chemical potential in producing sugar-derived compounds. These compounds have significant applications in generating new chemical scaffolds for drug discovery and chemical biology.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 39","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202483901","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452380","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Brendan Horst, Leopoldo J. Gabella Carena, Michael T. Doppert, Rens Ham, Thomas Hansen, Eelco Ruijter
Based on the successful application of a nitroaryl transfer cascade reaction in the total synthesis of various monoterpene indole alkaloids proceeding via fused bicyclic intermediate, we investigated analogous cascade reactions involving spiro, bridged, and alternatively fused bicyclic intermediates. Unfortunately, none of these was found to afford the desired nitroaryl transfer product. DFT studies of the original cascade process revealed that the Truce-Smiles rearrangement is the rate-determining step. In addition, we found that the subsequent SO2 extrusion is accompanied by retro-Mannich ring opening, resulting in a stabilized enolate that only recyclizes after activation of the cyclic imine moiety. Computation of the reaction profiles of the proposed alternative cascade reactions showed that the barrier for the Truce-Smiles rearrangement is unreasonably high for the bridged and alternatively fused systems, but only moderately higher for the five-membered spiro system. Reasoning that even more electron-deficient arenesulfonamides should have a lower barrier for the Truce-Smiles rearrangement, we synthesized the corresponding 2,4-dinitrobenzenesulfonamide precursor and found that it indeed smoothly undergoes the nitroaryl transfer cascade at room temperature. In this case, however, the cascade reaction produces a cyclic imine product, as the intermediate 2,4-dinitrophenyl-substituted enolate is insufficiently nucleophilic to undergo the Mannich cyclization.
{"title":"Computation-Guided Scope Exploration of a Conjugate Addition/Truce-Smiles Cascade Reaction for Scaffold Diversification","authors":"Brendan Horst, Leopoldo J. Gabella Carena, Michael T. Doppert, Rens Ham, Thomas Hansen, Eelco Ruijter","doi":"10.1002/ejoc.202400870","DOIUrl":"https://doi.org/10.1002/ejoc.202400870","url":null,"abstract":"Based on the successful application of a nitroaryl transfer cascade reaction in the total synthesis of various monoterpene indole alkaloids proceeding via fused bicyclic intermediate, we investigated analogous cascade reactions involving spiro, bridged, and alternatively fused bicyclic intermediates. Unfortunately, none of these was found to afford the desired nitroaryl transfer product. DFT studies of the original cascade process revealed that the Truce-Smiles rearrangement is the rate-determining step. In addition, we found that the subsequent SO2 extrusion is accompanied by retro-Mannich ring opening, resulting in a stabilized enolate that only recyclizes after activation of the cyclic imine moiety. Computation of the reaction profiles of the proposed alternative cascade reactions showed that the barrier for the Truce-Smiles rearrangement is unreasonably high for the bridged and alternatively fused systems, but only moderately higher for the five-membered spiro system. Reasoning that even more electron-deficient arenesulfonamides should have a lower barrier for the Truce-Smiles rearrangement, we synthesized the corresponding 2,4-dinitrobenzenesulfonamide precursor and found that it indeed smoothly undergoes the nitroaryl transfer cascade at room temperature. In this case, however, the cascade reaction produces a cyclic imine product, as the intermediate 2,4-dinitrophenyl-substituted enolate is insufficiently nucleophilic to undergo the Mannich cyclization.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"110 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452164","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A novel and highly efficient methodology for the synthesis of 2,4,6-triaryl-1,3,5-triazines and 2,4,6-trisubstituted pyrimidines from amidines and alcohols has been established. Using the Earth-abundant and air-stable chromium salt catalyst and the phosphine-free ligand, the developed Cr-catalyzed acceptorless dehydrogenative coupling provides 1,3,5-triazines and pyrimidines with high yields and good functional group tolerance. Moreover, the synthetic value of this operationally simple protocol was demonstrated by gram-scale experiment and the synthesis of the linker to construct various supramolecular complexes.
{"title":"A Chromium Catalytic System for the Synthesis of Aryl-Substituted 1,3,5-Triazines and Pyrimidines by Acceptorless Dehydrogenative Coupling","authors":"Baojin Feng, Wantong Yue, Dongyue Wei, Qing Chen, Chuanqi Liu, Xiaoqian Wang, Yilei Wang, Zhihua Peng","doi":"10.1002/ejoc.202400993","DOIUrl":"https://doi.org/10.1002/ejoc.202400993","url":null,"abstract":"A novel and highly efficient methodology for the synthesis of 2,4,6-triaryl-1,3,5-triazines and 2,4,6-trisubstituted pyrimidines from amidines and alcohols has been established. Using the Earth-abundant and air-stable chromium salt catalyst and the phosphine-free ligand, the developed Cr-catalyzed acceptorless dehydrogenative coupling provides 1,3,5-triazines and pyrimidines with high yields and good functional group tolerance. Moreover, the synthetic value of this operationally simple protocol was demonstrated by gram-scale experiment and the synthesis of the linker to construct various supramolecular complexes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142449285","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Robin Schulte, Dustin Schade, Thomas Paululat, Heiko Ihmels
The photochromic norbornadiene‐quadricyclane cycle has emerged as a promising basis for molecular solar thermal (MOST) energy storage. In this context, it has been established that multifunctional photoswitches with several norbornadiene units at one central aromatic core have favorable photochemical properties and storage capacities. Nevertheless, a maximum number of three norbornadiene units has been combined in one molecule, so far. In this work, scope and limits of this approach should be further assessed. Thus, exemplary polyfunctionalized derivatives have been synthesized by Suzuki‐Miyaura reactions, and their suitability for MOST applications was investigated. These compounds were converted into the corresponding quadricyclanes by direct UV irradiation (λex = 315 nm) with moderate quantum yields, whereas the reaction is more efficient upon irradiation with λex = 520 nm in the presence of photosensitizers. But these molecules showed low stabilities and short half‐lifes of 1 to 2 days. Moreover, the photochemical reaction is hampered by the close vicinity of photoactive units. Therefore, it appears that in such assemblies, a maximum number of three norbornadiene units is the limit to keep the optimal balance of photochemical properties required for MOST applications.
光致变色降冰片二烯-四环烷循环已成为分子太阳能热（MOST）储能的一个有前途的基础。在这种情况下，已经证实在一个芳香族中心核上含有多个降冰片二烯单元的多功能光开关具有良好的光化学特性和储能能力。不过，迄今为止，在一个分子中最多只能结合三个降冰片二烯单元。在这项工作中，应进一步评估这种方法的范围和局限性。因此，我们通过 Suzuki-Miyaura 反应合成了多官能化衍生物，并研究了它们在 MOST 应用中的适用性。通过紫外线直接照射（λex = 315 纳米），这些化合物转化为相应的四环化合物，量子产率适中，而在光敏剂存在的情况下，用 λex = 520 纳米照射，反应效率更高。但这些分子的稳定性较低，半衰期较短，仅为 1 到 2 天。此外，光化学反应还受到光活性单元邻近的阻碍。因此，在这种组合物中，要保持 MOST 应用所需的光化学特性的最佳平衡，最多只能有三个降冰片二烯单元。
{"title":"Gilding the Lily: Studies on the Effects of Successive Loading of Light Energy‐Storing Molecules with Norbornadiene Units","authors":"Robin Schulte, Dustin Schade, Thomas Paululat, Heiko Ihmels","doi":"10.1002/ejoc.202401090","DOIUrl":"https://doi.org/10.1002/ejoc.202401090","url":null,"abstract":"The photochromic norbornadiene‐quadricyclane cycle has emerged as a promising basis for molecular solar thermal (MOST) energy storage. In this context, it has been established that multifunctional photoswitches with several norbornadiene units at one central aromatic core have favorable photochemical properties and storage capacities. Nevertheless, a maximum number of three norbornadiene units has been combined in one molecule, so far. In this work, scope and limits of this approach should be further assessed. Thus, exemplary polyfunctionalized derivatives have been synthesized by Suzuki‐Miyaura reactions, and their suitability for MOST applications was investigated. These compounds were converted into the corresponding quadricyclanes by direct UV irradiation (λex = 315 nm) with moderate quantum yields, whereas the reaction is more efficient upon irradiation with λex = 520 nm in the presence of photosensitizers. But these molecules showed low stabilities and short half‐lifes of 1 to 2 days. Moreover, the photochemical reaction is hampered by the close vicinity of photoactive units. Therefore, it appears that in such assemblies, a maximum number of three norbornadiene units is the limit to keep the optimal balance of photochemical properties required for MOST applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"54 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142449457","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ting Tang, Ying Han, Chao-Guo Yan, Kun Huang, Jing Sun
A convenient synthetic protocol for diverse functionalized dihydrobenzofuran-fused spirocyclopentane-1,2-diindolin-ones with high diastereoselectivity is developed by base promoted domino annulation reaction of MBH carbonates of isatins and 3-(o-hydroxybenzylidene)indolin-2-ones. The relative configurations of the various polycyclic compounds are clearly elucidated by determination eight single crystal structures.
{"title":"Convenient Synthesis of Dihydrobenzofuran-Fused Spirocyclopentane-1,2-Diindolinone Scaffolds","authors":"Ting Tang, Ying Han, Chao-Guo Yan, Kun Huang, Jing Sun","doi":"10.1002/ejoc.202400777","DOIUrl":"https://doi.org/10.1002/ejoc.202400777","url":null,"abstract":"A convenient synthetic protocol for diverse functionalized dihydrobenzofuran-fused spirocyclopentane-1,2-diindolin-ones with high diastereoselectivity is developed by base promoted domino annulation reaction of MBH carbonates of isatins and 3-(<i>o</i>-hydroxybenzylidene)indolin-2-ones. The relative configurations of the various polycyclic compounds are clearly elucidated by determination eight single crystal structures.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142444473","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Two cycloaddition modes of isoquinolinium 1,4-zwitterionic thiolates have been established. Upon choosing α-bromo ketones as the counterpart, a range of isoquinoline-fused thiazines can be attained with yields ranging from moderate to excellent through a formal [5 + 1] reaction pathway, exhibiting remarkable substrate adaptability and resilience to diverse functional groups. Additionally, a library of unprecedented thiazepino[5,4-a]isoquinolines, a novel category of seven-membered heterocycles, has been synthesized via a [5 + 2] pathway utilizing acetylenedicarboxylate as the reactive component. Notably, this reaction process stands out for its exceptional 100% atomic utilization efficiency.
{"title":"Assembly of Thiazino[3,4-a]isoquinoline and Thiazepino[5,4-a]isoquinoline Frameworks from Isoquinolinium 1,4-Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions","authors":"Hang-Dong Zuo, Ji-Yun Wang, Yu-Ting Wang, Xiao Zou, Xi Chen, Sheng-Hu Yan, Yue Zhang, Jia-Fa Shen","doi":"10.1002/ejoc.202401020","DOIUrl":"https://doi.org/10.1002/ejoc.202401020","url":null,"abstract":"Two cycloaddition modes of isoquinolinium 1,4-zwitterionic thiolates have been established. Upon choosing α-bromo ketones as the counterpart, a range of isoquinoline-fused thiazines can be attained with yields ranging from moderate to excellent through a formal [5 + 1] reaction pathway, exhibiting remarkable substrate adaptability and resilience to diverse functional groups. Additionally, a library of unprecedented thiazepino[5,4-a]isoquinolines, a novel category of seven-membered heterocycles, has been synthesized via a [5 + 2] pathway utilizing acetylenedicarboxylate as the reactive component. Notably, this reaction process stands out for its exceptional 100% atomic utilization efficiency.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"58 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142448435","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Marcio C. S. de Mattos, Carlos Vinícius Pinto dos Santos
A systematic mechanistic study employing kobs kineticsmeasurements, linear free‐energy relationship, hydrogen kinetic isotope effect and rate law, as well as the Density Functional Theory (DFT) approach (M06‐2x/6‐311G(d,p)) for the oxidation of diverse substituted benzyl alcohols with trichloroisocyanuric acid (TCCA) / H2O in 50 % MeCN / CH2Cl2 at 25.0 °C is present. The kinetic results showed an autocatalytic behavior and a primary kinetic isotope effect (4.22). The linear free‐energy relationship (σ, ρ = ‐1.22) indicated a mechanism change for 4‐CF3, 3‐NO2 and 4‐NO2 substituted benzyl alcohols and a fractional rate law (3.25) for benzyl alcohol. The DFT results indicated Cl2, formed in situ from TCCA and the benzyl alcohol, as the actual oxidizing species. Furthermore, calculations support the kinetic results with high agreement through a transition state that performs a hydride abstraction by autocatalytic Cl2 in the induction zone. In the case of substrates bearing strong electron withdrawing groups, the mechanism changes to hydrogen abstraction from the corresponding benzyl hypochlorite as the main pathway.
{"title":"A Mechanistic Study of the Oxidation of Substituted Benzyl Alcohols with Trichloroisocyanuric Acid","authors":"Marcio C. S. de Mattos, Carlos Vinícius Pinto dos Santos","doi":"10.1002/ejoc.202400834","DOIUrl":"https://doi.org/10.1002/ejoc.202400834","url":null,"abstract":"A systematic mechanistic study employing kobs kineticsmeasurements, linear free‐energy relationship, hydrogen kinetic isotope effect and rate law, as well as the Density Functional Theory (DFT) approach (M06‐2x/6‐311G(d,p)) for the oxidation of diverse substituted benzyl alcohols with trichloroisocyanuric acid (TCCA) / H2O in 50 % MeCN / CH2Cl2 at 25.0 °C is present. The kinetic results showed an autocatalytic behavior and a primary kinetic isotope effect (4.22). The linear free‐energy relationship (σ, ρ = ‐1.22) indicated a mechanism change for 4‐CF3, 3‐NO2 and 4‐NO2 substituted benzyl alcohols and a fractional rate law (3.25) for benzyl alcohol. The DFT results indicated Cl2, formed in situ from TCCA and the benzyl alcohol, as the actual oxidizing species. Furthermore, calculations support the kinetic results with high agreement through a transition state that performs a hydride abstraction by autocatalytic Cl2 in the induction zone. In the case of substrates bearing strong electron withdrawing groups, the mechanism changes to hydrogen abstraction from the corresponding benzyl hypochlorite as the main pathway.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142444023","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Akshay Kumawat, Sumbul Mansuri, Mary Sravani Galla, Nagula Shankaraiah
A rapid metal-free approach describing one-pot thiocyanation of chromone and coumarin enabling tandem cyclization via potassium thiocyanate as a sulfur surrogate was unveiled. Interestingly, this enaminone-mediated protocol facilitated straightforward access to medicinally significant 2-amino/imino thiazolo fused chromone and coumarin frameworks. This methodology provided good atom-economy, remarkable functional group tolerance, and scalability. Alongside establishing a wide substrate scope, it also provided a feasible scalability up to gram scale.
{"title":"KSCN-mediated one-pot thiocyanation tandem cyclization of enaminones: a facile access to 2-amino/imino thiazolo fused chromone and coumarin frameworks","authors":"Akshay Kumawat, Sumbul Mansuri, Mary Sravani Galla, Nagula Shankaraiah","doi":"10.1002/ejoc.202400690","DOIUrl":"https://doi.org/10.1002/ejoc.202400690","url":null,"abstract":"A rapid metal-free approach describing one-pot thiocyanation of chromone and coumarin enabling tandem cyclization via potassium thiocyanate as a sulfur surrogate was unveiled. Interestingly, this enaminone-mediated protocol facilitated straightforward access to medicinally significant 2-amino/imino thiazolo fused chromone and coumarin frameworks. This methodology provided good atom-economy, remarkable functional group tolerance, and scalability. Alongside establishing a wide substrate scope, it also provided a feasible scalability up to gram scale.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142448132","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient catalytic system employing TMS•OTf for the regioselective thiolation of electron-rich arenes with sulfonyl hydrazides has been developed. The reaction occurs in a solvent mixture of dichloroethane and trifluoroethanol under mild conditions, with the addition of water. This method furnishes a range of para-thio-substituted arenes and 3-sulfenyl-indoles in good to excellent yields, marking a significant advancement in organic synthesis.
{"title":"Lewis acid-promoted C–H Chalcogenation of Arenes and Heteroarenes","authors":"Rahul Vishwakarma, Pragya Sharma, Chinmoy Kumar Hazra","doi":"10.1002/ejoc.202400894","DOIUrl":"https://doi.org/10.1002/ejoc.202400894","url":null,"abstract":"An efficient catalytic system employing TMS•OTf for the regioselective thiolation of electron-rich arenes with sulfonyl hydrazides has been developed. The reaction occurs in a solvent mixture of dichloroethane and trifluoroethanol under mild conditions, with the addition of water. This method furnishes a range of para-thio-substituted arenes and 3-sulfenyl-indoles in good to excellent yields, marking a significant advancement in organic synthesis.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"60 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142440812","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A binary mixture of organic salts, also known as ionic liquids, [C12mim][Br]:[MPIM][HCOO] denoted as BmIL1 has been ex-plored as bifunctional catalyst for the selective synthesis of 2 -phenylquinazolin-4(3H)-ones and 2,3-dihydroquinazolin-(1H)-ones from same precursors under metal, ligand and additive free conditions. The methodology has been extended to the synthesis of 2-phenylquinazolin-4(3H)-ones via another pathway from different precursors under the same catalytic system. Greener synthesis of existing drugs reestablished the multifunctionality of BmIL1. Gram scale synthesis of both the products, DFT calculations and sc-XRD data add significance to the developed protocol. Moreover, high atom economy and eco-scale values justify the sustainability of the methodology.
{"title":"Selective Access to 2-Phenylquinazolin-4(3H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones from Same Precursors in Organic Salts Derived DES","authors":"Bidyutjyoti Dutta, Ramyata Priyam Borah, Lahoucine Bahsis, Apurba Dutta, Bipul Sarma, Kuldeep Singh, Arvind Kumar, Diganta Sarma","doi":"10.1002/ejoc.202400789","DOIUrl":"https://doi.org/10.1002/ejoc.202400789","url":null,"abstract":"A binary mixture of organic salts, also known as ionic liquids, [C12mim][Br]:[MPIM][HCOO] denoted as BmIL1 has been ex-plored as bifunctional catalyst for the selective synthesis of 2 -phenylquinazolin-4(3H)-ones and 2,3-dihydroquinazolin-(1H)-ones from same precursors under metal, ligand and additive free conditions. The methodology has been extended to the synthesis of 2-phenylquinazolin-4(3H)-ones via another pathway from different precursors under the same catalytic system. Greener synthesis of existing drugs reestablished the multifunctionality of BmIL1. Gram scale synthesis of both the products, DFT calculations and sc-XRD data add significance to the developed protocol. Moreover, high atom economy and eco-scale values justify the sustainability of the methodology.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"66 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142440813","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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