An efficient, and easy method for the synthesis of 1,3,5- substituted 1,2,4-triazole derivatives by [3+2] annulation reactions of hydrazones with aldehydes, alkenes, or amines has been established. This strategy is characterized by the use of inexpensive and readily available oxidants and starting materials, a broader substrate scope, and moderate to good yields.
{"title":"Facile Synthesis of Diverse 1,3,5-Trisubstituted 1,2,4-Triazole using Hydrazones with Aldehydes, Alkenes, Amines","authors":"Yi Liu, Kunyi Zhang, Jialiang Zhang, Shuaikun Liu, Yu Song, Xinqiang Tan, Lizhen Fang","doi":"10.1002/ajoc.202400424","DOIUrl":"https://doi.org/10.1002/ajoc.202400424","url":null,"abstract":"An efficient, and easy method for the synthesis of 1,3,5- substituted 1,2,4-triazole derivatives by [3+2] annulation reactions of hydrazones with aldehydes, alkenes, or amines has been established. This strategy is characterized by the use of inexpensive and readily available oxidants and starting materials, a broader substrate scope, and moderate to good yields.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142253008","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}
Photoswitchable fluorescent self-assemblies exhibiting aggregation-induced emission (AIE) properties have garnered widespread attention. Due to their great adaptiveness and responsiveness towards different wavelengths required by photoreaction, photo-isomerization, and photoluminescence excitation, these fluorescent self-assemblies show diverse emission behavior in a spatial, temporal, and polychromatic manner. Integrating organic photoswitches and AIE fluorophores, these photoluminescent nano-assemblies has been proven to be an effective approach, allowing the development of sophisticated systems for drug release and cell regulation that can be precisely manipulated through light or other stimuli. This review systematically encapsulates recent advances in photoswitchable fluorescent self-assemblies under multi-scenario biological applications. The construction of photoswitchable AIE fluorophores through covalent and non-covalent interactions and their multimodal regulation are detailed, along with their biological applications in biosensing, bioimaging, and drug therapy.
{"title":"Photoswitchable AIE-Active Supramolecular Self-Assemblies for Biosensing and Bioimaging","authors":"Fengfan Zhu, Xiao-Fang Hou, Juping Wang, Lei Bi, Jiancheng Zhou, Xu-Man Chen","doi":"10.1002/ajoc.202400385","DOIUrl":"https://doi.org/10.1002/ajoc.202400385","url":null,"abstract":"Photoswitchable fluorescent self-assemblies exhibiting aggregation-induced emission (AIE) properties have garnered widespread attention. Due to their great adaptiveness and responsiveness towards different wavelengths required by photoreaction, photo-isomerization, and photoluminescence excitation, these fluorescent self-assemblies show diverse emission behavior in a spatial, temporal, and polychromatic manner. Integrating organic photoswitches and AIE fluorophores, these photoluminescent nano-assemblies has been proven to be an effective approach, allowing the development of sophisticated systems for drug release and cell regulation that can be precisely manipulated through light or other stimuli. This review systematically encapsulates recent advances in photoswitchable fluorescent self-assemblies under multi-scenario biological applications. The construction of photoswitchable AIE fluorophores through covalent and non-covalent interactions and their multimodal regulation are detailed, along with their biological applications in biosensing, bioimaging, and drug therapy.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"100 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142253005","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}
5,15-Porphyrinquinone is a non-aromatic and electron-deficient porphyrinoid that acts as an important framework for the synthesis of porphyrinoid derivatives. Generally, meso-functionalized A2-porphyrinquinone is synthesized via the oxidation of A2-porphyrin. Herein, we present the stereoselective synthesis of AB-porphyrinquinone Pt(II) complexes using the corresponding dipyrrinato-Pt complexes and bisformyldipyrrins. The reaction involves cyclization and oxidative aromatization induced by the Pt template, followed by oxidation using a mild MnO2 oxidant.
{"title":"Stereoselective Synthesis of AB-5,15-Porphyrinquinone Platinum(II) Complexes","authors":"Ryo Inoue, Iori Yamada, Momoka Yokoyama, Yasuhiro Morisaki","doi":"10.1002/ajoc.202400375","DOIUrl":"https://doi.org/10.1002/ajoc.202400375","url":null,"abstract":"5,15-Porphyrinquinone is a non-aromatic and electron-deficient porphyrinoid that acts as an important framework for the synthesis of porphyrinoid derivatives. Generally, meso-functionalized A2-porphyrinquinone is synthesized via the oxidation of A2-porphyrin. Herein, we present the stereoselective synthesis of AB-porphyrinquinone Pt(II) complexes using the corresponding dipyrrinato-Pt complexes and bisformyldipyrrins. The reaction involves cyclization and oxidative aromatization induced by the Pt template, followed by oxidation using a mild MnO2 oxidant.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142253006","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}
Deep J. Kalita, Pratiksha Bhorali, Supriya Khundrakpam, Sanjib Gogoi
A Rh(III)‐catalyzed annulation reaction of 2‐(2‐nitrovinyl)phenols and disubstituted alkynes is developed to complete the first synthesis of biologically important 4‐nitro substituted benzo[b]oxepines. The same reaction conditions are also applied for the efficient synthesis of 4‐cyano substituted benzo[b]oxepines which have high biological significance. Some of the synthesized 4‐nitrobenzo[b]oxepines are easily transformed to triazole fused dibenzo[b]oxepines.
{"title":"Rhodium(III)‐Catalyzed (5 + 2) Annulation Reaction for the Synthesis of Nitro and Cyano Substituted Benzo[b]oxepines","authors":"Deep J. Kalita, Pratiksha Bhorali, Supriya Khundrakpam, Sanjib Gogoi","doi":"10.1002/ajoc.202400392","DOIUrl":"https://doi.org/10.1002/ajoc.202400392","url":null,"abstract":"A Rh(III)‐catalyzed annulation reaction of 2‐(2‐nitrovinyl)phenols and disubstituted alkynes is developed to complete the first synthesis of biologically important 4‐nitro substituted benzo[b]oxepines. The same reaction conditions are also applied for the efficient synthesis of 4‐cyano substituted benzo[b]oxepines which have high biological significance. Some of the synthesized 4‐nitrobenzo[b]oxepines are easily transformed to triazole fused dibenzo[b]oxepines.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"209 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142252815","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}
Varun Rawat, Garima Sachdeva, Komal Rathi, Ved Prakash Verma
Catalysis plays a crucial role in modern chemistry, with macrocyclic compounds like calixarenes serving as key players in organic transformations through supramolecular chemistry. These macrocycles, synthesized from phenol and formaldehyde condensation, exhibit a variety of conformations, such as cone and partial-cone, due to their flexible structures. Their effectiveness as catalysts arises from their lipophilic cavities and the ease of functionalization on both the upper and lower rims. Water-soluble calixarenes, in particular, have gained attention for their ability to interact with hydrophobic cavities, facilitating molecular recognition in aqueous environments. A landmark achievement in this field was Shinkai's synthesis of water-soluble calix[4]arene in 1984, which involved sulphonation using tert-butyl groups, resulting in compounds known for their low toxicity and encapsulation capabilities. This review provides a comprehensive overview of the advancements in sulphonated calixarenes as catalysts, emphasizing their diverse applications and potential for future development. Key catalytic reactions and their substrate scopes are discussed, along with future perspectives on how these compounds can further revolutionize catalytic processes.
{"title":"Exploring Sulphonated Calix[n]arenes as Catalysts in Organic Reactions","authors":"Varun Rawat, Garima Sachdeva, Komal Rathi, Ved Prakash Verma","doi":"10.1002/ajoc.202400361","DOIUrl":"https://doi.org/10.1002/ajoc.202400361","url":null,"abstract":"Catalysis plays a crucial role in modern chemistry, with macrocyclic compounds like calixarenes serving as key players in organic transformations through supramolecular chemistry. These macrocycles, synthesized from phenol and formaldehyde condensation, exhibit a variety of conformations, such as cone and partial-cone, due to their flexible structures. Their effectiveness as catalysts arises from their lipophilic cavities and the ease of functionalization on both the upper and lower rims. Water-soluble calixarenes, in particular, have gained attention for their ability to interact with hydrophobic cavities, facilitating molecular recognition in aqueous environments. A landmark achievement in this field was Shinkai's synthesis of water-soluble calix[4]arene in 1984, which involved sulphonation using tert-butyl groups, resulting in compounds known for their low toxicity and encapsulation capabilities. This review provides a comprehensive overview of the advancements in sulphonated calixarenes as catalysts, emphasizing their diverse applications and potential for future development. Key catalytic reactions and their substrate scopes are discussed, along with future perspectives on how these compounds can further revolutionize catalytic processes.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269105","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}
Rajasekhara Reddy Sabbasani, P Krishnaraj, Sathi Bhulakshmi -, Lin Chun Cheng, Treesa Mary Chacko
A convenient, direct, one‐pot highly efficient microwave‐assisted synthesis of biomass‐derived D‐glucose‐based hydroxide ionic liquid via a simple three‐step approach has been described. The key features of the method include rapidness, eco‐friendliness, and excellent yields. To the best of our knowledge, this is the first methodology for synthesizing D‐Glucose‐based sugar ionic liquid (GSIL) under microwave irradiation. The developed catalyst allowed us to synthesize diverse dihydropyrano[3,2‐c]‐chromenes upto 95% yield in 30‐90 min stirring at 80 ̊C under mild conditions. The scope of the study was investigated using 30 instances. Developed GSILs exhibited excellent catalytic activity as well as good recyclability. Overall, the catalyst showed excellent value in green chemistry parameters such as atom economy (95%), E‐factor (0.05), carbon efficiency (100%), process mass intensity (1.62), and reaction mass efficiency (0.860).
{"title":"Sustainable Synthesis of D‐Glucose Based IL: A Renewable Organo Catalyst for the Efficient Synthesis of Dihydropyrano Coumarins","authors":"Rajasekhara Reddy Sabbasani, P Krishnaraj, Sathi Bhulakshmi -, Lin Chun Cheng, Treesa Mary Chacko","doi":"10.1002/ajoc.202400202","DOIUrl":"https://doi.org/10.1002/ajoc.202400202","url":null,"abstract":"A convenient, direct, one‐pot highly efficient microwave‐assisted synthesis of biomass‐derived D‐glucose‐based hydroxide ionic liquid via a simple three‐step approach has been described. The key features of the method include rapidness, eco‐friendliness, and excellent yields. To the best of our knowledge, this is the first methodology for synthesizing D‐Glucose‐based sugar ionic liquid (GSIL) under microwave irradiation. The developed catalyst allowed us to synthesize diverse dihydropyrano[3,2‐c]‐chromenes upto 95% yield in 30‐90 min stirring at 80 ̊C under mild conditions. The scope of the study was investigated using 30 instances. Developed GSILs exhibited excellent catalytic activity as well as good recyclability. Overall, the catalyst showed excellent value in green chemistry parameters such as atom economy (95%), E‐factor (0.05), carbon efficiency (100%), process mass intensity (1.62), and reaction mass efficiency (0.860).","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"75 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142253009","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}
Nian-Xuan Lin, Shih-Ming Chang, Xin-Shun Chiou, Kelly Lee, Yu-Tung Tsai, Prof. Dr. Cheng-Kun Lin
In article number e202400188, Cheng-Kun Lin and co-workers present a method to convert epoxy carbamates to oxazolidinones by combining intermolecular nucleophilic epoxide ring opening with intramolecular acyl substitution in a single step, enabling rapid conversion. It demonstrates favourable reactivity across various aryl groups, benzyl, or tert-butyl carbamates, consistently yielding satisfactory results, with oxazolidinone formation ranging from 55% to 99% across over 24 examples.
{"title":"Front Cover: Rapidly Diverse Synthesis of N-Aryl-5-Substituted-2-Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates (Asian J. Org. Chem. 9/2024)","authors":"Nian-Xuan Lin, Shih-Ming Chang, Xin-Shun Chiou, Kelly Lee, Yu-Tung Tsai, Prof. Dr. Cheng-Kun Lin","doi":"10.1002/ajoc.202480901","DOIUrl":"https://doi.org/10.1002/ajoc.202480901","url":null,"abstract":"<p>In article number e202400188, Cheng-Kun Lin and co-workers present a method to convert epoxy carbamates to oxazolidinones by combining intermolecular nucleophilic epoxide ring opening with intramolecular acyl substitution in a single step, enabling rapid conversion. It demonstrates favourable reactivity across various aryl groups, benzyl, or tert-butyl carbamates, consistently yielding satisfactory results, with oxazolidinone formation ranging from 55% to 99% across over 24 examples.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 9","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202480901","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142233196","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Catalytic kinetic resolutions of racemic carboxylic acids are important methods for preparing chiral carboxylic acids in their optically active forms. While several effective methods for the catalytic kinetic resolution of chiral α‐tertiary carboxylic acids have been reported, the efficient kinetic resolution of α‐quaternary carboxylic acids remains a significant challenge. In this context, we aimed to develop methods for the kinetic resolution of α‐quaternary carboxylic acids. Our approach involves a BINOL‐derived chiral bifunctional sulfide‐catalyzed bromolactonization technique, which was developed by our research group. In this work, we report the kinetic resolution of α‐allyl‐α‐cinnamyl carboxylic acids bearing an α‐quaternary stereocenter via chemo‐ and stereoselective bromolactonizations. The use of a BINOL‐derived chiral bifunctional sulfide catalyst with a hydroxy group was key for the efficient kinetic resolution of racemic α‐allyl‐α‐cinnamyl carboxylic acids.
{"title":"Kinetic Resolution of α‐Allyl‐α‐cinnamyl Carboxylic Acids Bearing an All‐Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide","authors":"Ken Okuno, Sao Sumida, Seiji Shirakawa","doi":"10.1002/ajoc.202400405","DOIUrl":"https://doi.org/10.1002/ajoc.202400405","url":null,"abstract":"Catalytic kinetic resolutions of racemic carboxylic acids are important methods for preparing chiral carboxylic acids in their optically active forms. While several effective methods for the catalytic kinetic resolution of chiral α‐tertiary carboxylic acids have been reported, the efficient kinetic resolution of α‐quaternary carboxylic acids remains a significant challenge. In this context, we aimed to develop methods for the kinetic resolution of α‐quaternary carboxylic acids. Our approach involves a BINOL‐derived chiral bifunctional sulfide‐catalyzed bromolactonization technique, which was developed by our research group. In this work, we report the kinetic resolution of α‐allyl‐α‐cinnamyl carboxylic acids bearing an α‐quaternary stereocenter via chemo‐ and stereoselective bromolactonizations. The use of a BINOL‐derived chiral bifunctional sulfide catalyst with a hydroxy group was key for the efficient kinetic resolution of racemic α‐allyl‐α‐cinnamyl carboxylic acids.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217077","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}
A fluorescence‐labeled nucleotide with a cleavable triazene linker was designed and synthesized as a potential reversible terminator for DNA sequencing by synthesis (SBS). The key intermediate, a triazene‐modified nucleotide, was successfully synthesized through the triazenylation of an amino‐modified nucleotide, followed by fluorescence labeling to yield the desired product. The synthesized triazene‐modified nucleotide can effectively serve as a substrate for Klenow Fragment (exo‐) DNA polymerase and be incorporated into DNA strands. Once the first modified nucleotide is incorporated, no further extension is possible, even with an unblocked 3'‐OH group. After the fluorescent label is completely removed under acidic conditions, the triazene reversible terminator can be incorporated into DNA strands again, thereby enabling the DNA sequencing cycles.
我们设计并合成了一种带有可裂解三氮烯连接体的荧光标记核苷酸，作为 DNA 合成测序（SBS）的潜在可逆终止子。通过对氨基修饰的核苷酸进行三嗪化，然后进行荧光标记，成功合成了关键的中间体--三嗪修饰的核苷酸，并得到了所需的产物。合成的三嗪修饰核苷酸可以有效地作为克伦诺片段（外）DNA 聚合酶的底物，并被整合到 DNA 链中。一旦第一个修饰的核苷酸被整合进去，就不可能再进一步延伸，即使是未被阻断的 3'-OH 基团也是如此。在酸性条件下，荧光标签被完全去除后，三嗪可逆终止剂可再次与 DNA 链结合，从而实现 DNA 测序循环。
{"title":"Synthesis and Evaluations of Cleavable Triazene‐Modified Nucleotide for DNA Sequencing","authors":"Pingyang Wang, Bowei Tang, Yu-Mei Shen","doi":"10.1002/ajoc.202400393","DOIUrl":"https://doi.org/10.1002/ajoc.202400393","url":null,"abstract":"A fluorescence‐labeled nucleotide with a cleavable triazene linker was designed and synthesized as a potential reversible terminator for DNA sequencing by synthesis (SBS). The key intermediate, a triazene‐modified nucleotide, was successfully synthesized through the triazenylation of an amino‐modified nucleotide, followed by fluorescence labeling to yield the desired product. The synthesized triazene‐modified nucleotide can effectively serve as a substrate for Klenow Fragment (exo‐) DNA polymerase and be incorporated into DNA strands. Once the first modified nucleotide is incorporated, no further extension is possible, even with an unblocked 3'‐OH group. After the fluorescent label is completely removed under acidic conditions, the triazene reversible terminator can be incorporated into DNA strands again, thereby enabling the DNA sequencing cycles.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216967","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}
Nagula Shankaraiah, Mursalim A. Khan, Rajkumar Reddyrajula, Akash P. Sakla, Manda Sathish
The synthesis of tetrahydro-β-carbolines (THβCs) framework is a fundamental aspect of medicinal chemistry due to their significant pharmacological applications. Herein, we developed a microwave-assisted novel approach for the synthesis of THβC scaffolds utilizing ferrous(II) chloride as an earth abundant metal catalyst and methanol used as valuable methylene source. This methodology demonstrates excellent functional group tolerance and provides N2-substituted THβCs in good to excellent yields. Overall, this study highlights a sustainable and practical strategy for the synthesis of biologically important THβCs, thereby offering promising prospects in the drug discovery and development.
{"title":"Microwave-Assisted One-pot Synthesis of Tetrahydro-β-Carbolines by Fe(II)-Catalyst: Utilizing Methanol as Methylene Synthon","authors":"Nagula Shankaraiah, Mursalim A. Khan, Rajkumar Reddyrajula, Akash P. Sakla, Manda Sathish","doi":"10.1002/ajoc.202400404","DOIUrl":"https://doi.org/10.1002/ajoc.202400404","url":null,"abstract":"The synthesis of tetrahydro-β-carbolines (THβCs) framework is a fundamental aspect of medicinal chemistry due to their significant pharmacological applications. Herein, we developed a microwave-assisted novel approach for the synthesis of THβC scaffolds utilizing ferrous(II) chloride as an earth abundant metal catalyst and methanol used as valuable methylene source. This methodology demonstrates excellent functional group tolerance and provides N2-substituted THβCs in good to excellent yields. Overall, this study highlights a sustainable and practical strategy for the synthesis of biologically important THβCs, thereby offering promising prospects in the drug discovery and development.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216971","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}
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