Fei Yang , Fangqin Ren , Xuanzheng Liu , Dr. Mengna Zhao , Prof. Yifeng Zhou
{"title":"Design, Synthesis and Optical Properties of 2‐(1‐Azaazulenyl)pyrrole‐Boron Difluoride Complexes","authors":"Fei Yang , Fangqin Ren , Xuanzheng Liu , Dr. Mengna Zhao , Prof. Yifeng Zhou","doi":"10.1002/ajoc.202400804","DOIUrl":"10.1002/ajoc.202400804","url":null,"abstract":"<div><div>Herein, 1‐azaazulene‐based BF<sub>2</sub> complexes with pyrrole as the amido N‐donor were synthesized via Suzuki‐Miyaura cross coupling of 2‐bromo‐1‐azaazulene and 1‐Boc‐2‐pyrroleboronic acid. The structures, especially the unique N−B linkages, were discussed based on the single crystal analysis and DFT calculations. Compared to the parent BODIPY, the unsubstituted complex <strong>3 a</strong> exhibited similar absorption maximum and three times larger Stokes shift. The optical properties can be further tuned by introducing aryl substituents at the α‐position of pyrrole moiety.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202400804"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072540","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":"Zinc/Copper‐Catalyzed Skeletal Editing of Isoxazoles into Pyrroles Having Four Non‐Identical Substituents by [3+2] Annulation Reaction","authors":"Shivani Choudhary , Gayyur , Dr. Nayan Ghosh","doi":"10.1002/ajoc.202500108","DOIUrl":"10.1002/ajoc.202500108","url":null,"abstract":"<div><div>Pyrroles are frequently encountered in natural products, bioactive molecules and functional materials. Herein, a straightforward one pot zinc‐ and copper‐catalyzed protocol, converting isoxazoles into pyrroles upon reaction with bis(ynamides) via skeletal editing has been developed. Notably, various substituted isoxazoles and bis(ynamides) are well tolerated, offering densely functionalized pyrroles in moderate to good yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500108"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072555","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":"Catalyst‐free One‐Pot Synthesis of Sulfonyl Fluorides from Triazenes via Multicomponent Reaction","authors":"Truong Giang Luu , Hee‐Kwon Kim","doi":"10.1002/ajoc.202500104","DOIUrl":"10.1002/ajoc.202500104","url":null,"abstract":"<div><div>Sulfonyl fluorides are valuable structures in organic chemistry and drug discovery. In this study, a novel metal‐ and catalyst‐free method for synthesizing sulfonyl fluorides from aryltriazenes was developed. This reaction employed a one‐pot, multi‐component approach using aryltriazenes, DABSO, and NFSI in the presence of TFA. Using this method, a variety of sulfonyl fluorides was readily synthesized from aryltriazenes in high yields. This approach features simple reaction conditions, broad functional group tolerance, and ease of operation, proving an efficient and practical strategy for the preparation of sulfonyl fluorides.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500104"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072617","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}
Prof. Dr. Rui Umeda , Shigeru Morishita , Dr. Hiroyasu Sato , Prof. Dr. Yutaka Nishiyama
{"title":"Benzannulation Approach to Synthesis of Highly Elaborated Helical Molecules Having 2,3‐Disubstituted Naphthalene Units","authors":"Prof. Dr. Rui Umeda , Shigeru Morishita , Dr. Hiroyasu Sato , Prof. Dr. Yutaka Nishiyama","doi":"10.1002/ajoc.202500064","DOIUrl":"10.1002/ajoc.202500064","url":null,"abstract":"<div><div>In this study, we classified <em>ortho</em>‐phenylene‐naphthylene oligomers into three types <strong>II</strong>, <strong>III</strong>, and <strong>IV</strong> based on the sequence of phenylene and naphthylene units. Type <strong>II</strong> has an alternating sequence of phenylene and naphthylene units, type <strong>III</strong> has a phenylene‐naphthylene‐phenylene repeating structure, and type <strong>IV</strong> has a naphthylene‐phenylene‐naphthylene repeating structure. While type <strong>II</strong> has been studied in detail, there have been few reports on types <strong>III</strong> and <strong>IV</strong>. We report on the synthesis and photophysical properties of oligomers with type <strong>II</strong>, <strong>III</strong>, and <strong>IV</strong> substructures. Additionally, X‐ray crystallographic analysis confirmed that these oligomers adopt helical conformations.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500064"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072674","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}
Yasuaki Furuya , Ryuichi Nishiyori , Ken Okuno , Taiki Mori , Sao Sumida , Mina Yamakawa , Seiji Shirakawa
{"title":"Asymmetric Synthesis of γ‐Lactones Bearing α,γ‐Bis‐Quaternary Stereocenters via Chiral Bifunctional Sulfide‐Catalyzed Desymmetrizing Bromolactonization","authors":"Yasuaki Furuya , Ryuichi Nishiyori , Ken Okuno , Taiki Mori , Sao Sumida , Mina Yamakawa , Seiji Shirakawa","doi":"10.1002/ajoc.202500062","DOIUrl":"10.1002/ajoc.202500062","url":null,"abstract":"<div><div>The structure of highly substituted chiral γ‐lactones is found in many important natural products. Therefore, the development of methods for the catalytic asymmetric synthesis of highly substituted γ‐lactones is recognized as an important area of research. Catalytic asymmetric halolactonizations are known to be reliable methods for the stereoselective preparation of optically active γ‐lactones. However, catalytic asymmetric halolactonizations for the synthesis of highly substituted γ‐lactones, such as α,γ‐bis‐quaternary γ‐lactones with four different carbon substituents on the lactone backbone, remain underdeveloped. To address this limitation, we report here the diastereo‐ and enantioselective synthesis of α,γ‐bis‐quaternary γ‐lactones possessing four carbon substituents at the α‐ and γ‐positions, achieved through chiral bifunctional sulfide‐catalyzed desymmetrizing bromolactonization.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500062"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072677","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}
Dr. Nithya Murugesh , Saravanan Saranya , Dr. Packirisamy Kuzhalmozhi Madarasi , Rekha Muthuvel , Prof. Ramasamy Karvembu , Dr. Seenuvasan Vedachalam
{"title":"Synthetic Strategy of RITA Drug Enabled by N‐Heterocylic Carbene via 1,4‐Synthon Formation and DFT Studies**","authors":"Dr. Nithya Murugesh , Saravanan Saranya , Dr. Packirisamy Kuzhalmozhi Madarasi , Rekha Muthuvel , Prof. Ramasamy Karvembu , Dr. Seenuvasan Vedachalam","doi":"10.1002/ajoc.202400761","DOIUrl":"10.1002/ajoc.202400761","url":null,"abstract":"<div><div>This paper describes an efficient and convenient procedure to synthesize substituted symmetrical 1,4‐butanedione derivatives <em>via</em> a double Stetter reaction using divinyl sulfone and corresponding aldehydes with broad substrate scopes. A theoretical investigation and DFT calculation were studied to form 1,4‐di(thiophene‐2‐yl)butane‐1,4‐dione from thiophene‐2‐carboxaldehyde and the mechanism was proposed. A substrate 1,4‐di(thiophene‐2‐yl)butane‐1,4‐dione was subjected to Paal Knorr furan synthesis, Vilsmeier‐Haack di‐formylation followed by sodium borohydride reduction delivered the RITA drug.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202400761"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072679","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}
Prof. Kazuo Takimiya , Kamon Sahara , Masashi Inoue , Dr. Kirill Bulgarevich , Dr. Kohsuke Kawabata
{"title":"Isoelectronic Substitution of a High‐performance Organic Semiconductor with Selenium Atoms: Synthesis and Characterization of Methylthiolated Dibenzo[cd,gh][2,5]diselenapentalene","authors":"Prof. Kazuo Takimiya , Kamon Sahara , Masashi Inoue , Dr. Kirill Bulgarevich , Dr. Kohsuke Kawabata","doi":"10.1002/ajoc.202500173","DOIUrl":"10.1002/ajoc.202500173","url":null,"abstract":"<div><div>A selenium variant of one of the best molecular semiconductors, 1,3,6,8‐tetrakis(methylthio)pyrene (MT‐pyrene), namely 1,3,5,7‐tetrakis(methylthio)dibenzo[<em>cd</em>,<em>gh</em>][2,5]diselenapentalene (<strong>1</strong>), was designed, synthesized, and fully characterized through single‐crystal X‐ray analysis and single‐crystal field‐effect transistors. Although the crystal structure of <strong>1</strong> was a brickwork‐related structure similar to that of MT‐pyrene, the transport properties of <strong>1</strong> were far inferior to that of MT‐pyrene. This is attributed to subtle differences in the crystal structure, where the large displacement along the molecular short‐axis direction diminishes the efficient two‐dimensional overlap of HOMO. Since such displacement can be caused by steric congestion of three chalcogen atoms at both sides of <strong>1</strong>, two from the methylthio group and one from the core, we also synthesized 1,5‐bis(methylthio)dibenzo[<em>cd,gh</em>][2,5]diselenapentalene (<strong>2</strong>). However, <strong>2</strong> gave a less intermolecularly interactive crystal structure or one‐dimensional anisotropic structure, which were also not promising as molecular semiconductors, judging from the calculated electronic structures in the solid state. As the selenium‐containing core, dibenzo[<em>cd,gh</em>][2,5]diselenapentalene, has an isoelectronic molecular structure with pyrene and a smaller reorganization energy than pyrene, it is expected to be a promising π‐conjugated structure as organic semiconductors. However, methylthiolation was concluded not to be a suitable molecular‐design strategy to bring out the potential of the core.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500173"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072722","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":"Synthetic Approaches of Six Membered N‐Heterocycles Using Bridged N‐Based Ionic Liquids: A Review","authors":"Anvita Chaudhary , Richa Srivastava","doi":"10.1002/ajoc.202400785","DOIUrl":"10.1002/ajoc.202400785","url":null,"abstract":"<div><div>Six‐membered nitrogen‐containing heterocycles represent a significant class of compounds in organic chemistry and play a pivotal role in various fields. Conventional synthetic methods of these compounds have certain advantages, but they are also limited by many factors including environmental impacts. Nitrogen‐containing bridge‐head basic compounds like hexamethylenetetramine (HMTA), 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD), 1,4‐diazabicyclo[2.2.2]octane (DABCO), and 1,8‐diazabicyclo‐[5.4.0]undec‐7‐ene (DBU) have shown promising characteristics in developing task‐specific ionic liquids. These ionic liquids have been employed in synthesizing six‐membered nitrogen‐containing heterocyclic compounds in accordance with the principles of green and sustainable chemistry. Hence, this manuscript has been compiled on recent developments in the synthesis of six‐membered nitrogen‐containing heterocycles using bridge‐head nitrogen‐based ionic liquids. The manuscript covers studies published from 2013 onwards.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202400785"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072546","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":"Copper‐Catalyzed Oxidative Esterification and Amidation of Benzylic Hydrocarbons","authors":"Daisy Gogoi , Sauvik Kashyap , Hrishikesh Talukdar , Prodeep Phukan","doi":"10.1002/ajoc.202500137","DOIUrl":"10.1002/ajoc.202500137","url":null,"abstract":"<div><div>A new and efficient methodology has been developed using a Copper‐DMAP complex to perform C−O and C−N bond‐forming cross‐coupling reactions. The catalyst enables atom‐economic esterification, amidation, and sulfamidation of benzylic C−H bonds using benzoic acids, benzamides, and sulfonamides employing di‐<em>tert</em>‐butyl peroxide (DTBP) as the oxidant. The air‐stable and easy‐to‐prepare complex with low catalyst loading enables the base‐ and ligand‐free synthesis of a variety of benzyl esters, <em>N</em>‐benzyl benzamides, and <em>N</em>‐benzyl aryl sulfonamides in open‐air conditions with good to excellent yields within a short reaction time.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500137"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072551","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":"Dansyl Based AIE Material for Multimodal Recognition of Antibiotics","authors":"Shagun , Abhimanew Dhir","doi":"10.1002/ajoc.202500207","DOIUrl":"10.1002/ajoc.202500207","url":null,"abstract":"<div><div>A dansyl‐isoniazid conjugate (DISH) is designed and synthesized which exhibits Aggregation‐Induced Emission (AIE) in MeOH : H<sub>2</sub>O (20 : 80). This AIE Material is utilized for detection of different antibiotics having carboxylic acid, amide and thioamide functionalities. The material shows a multimodal recognition behaviour having maximum affinity with a fluorescence intensification (236 %) (φ=0.68) on addition of 2.0 μM levofloxacin (LEV) whereas the quenching of fluorescence emission is observed on addition of prothionamide (PTH) (8.0 μM). To test the practical application of the DISH, we performed smartphone‐based detection wherein RGB colour picker app is used to study the colour variation of probe in urine samples spiked with same concentration of LEV (2.0 μM) and PTH (8.0 μM).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 5","pages":"Article e202500207"},"PeriodicalIF":2.8,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072678","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}