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First Total Synthesis and Structural Elucidation of Microcystbiopterin C, a Pterin Glycoside From a Microcystis Bloom 微囊藻中蝶呤苷微囊生物terin C的首次全合成和结构解析
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-22 DOI: 10.1002/jhet.70214
Tadashi Hanaya, Katsuya Iwasaki
{"title":"First Total Synthesis and Structural Elucidation of Microcystbiopterin C, a Pterin Glycoside From a Microcystis Bloom","authors":"Tadashi Hanaya,&nbsp;Katsuya Iwasaki","doi":"10.1002/jhet.70214","DOIUrl":"https://doi.org/10.1002/jhet.70214","url":null,"abstract":"<div>\u0000 \u0000 <p>The first total synthesis and unambiguous structural elucidation of microcystbiopterin C, a pterin glycoside isolated from a <i>Microcystis</i> bloom, has been achieved. Two candidate biopterin glycosides (<b>5a</b> and <b>5b</b>) corresponding to the proposed structures of microcystbiopterin C were synthesized by glycosylation of a suitably protected biopterin derivative <b>10</b> with 2,4-di-<i>O</i>-benzoyl-6-deoxy-3-<i>O</i>-methyl-α-L-mannopyranosyl bromide (<b>9</b>) and the corresponding α-D-mannopyranosyl bromide (<b>22</b>), respectively, followed by stepwise deprotection. Detailed comparison of the NMR data and the specific rotation of compounds <b>5a</b> and <b>5b</b> with those of the natural product established that microcystbiopterin C possesses the structure of 2′-<i>O</i>-(6-deoxy-3-<i>O</i>-methyl-α-D-mannopyranosyl)biopterin (<b>5b</b>).</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1278-1287"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662597","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}
引用次数: 0
Regioselective Base-Induced Intramolecular Synthesis of Novel Pyrimido[1,6-a]Selenopheno[3,2-d]Pyrimidines 区域选择性碱基诱导的新型嘧啶[1,6-a]硒偶氮嘧啶[3,2-d]分子内合成
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-20 DOI: 10.1002/jhet.70212
Amin Mirfarah, Iman Farzamnezhad, Mohammad Amin Tokallou, Ali Shiri
{"title":"Regioselective Base-Induced Intramolecular Synthesis of Novel Pyrimido[1,6-a]Selenopheno[3,2-d]Pyrimidines","authors":"Amin Mirfarah,&nbsp;Iman Farzamnezhad,&nbsp;Mohammad Amin Tokallou,&nbsp;Ali Shiri","doi":"10.1002/jhet.70212","DOIUrl":"https://doi.org/10.1002/jhet.70212","url":null,"abstract":"<div>\u0000 \u0000 <p>In this study, we present an efficient and regioselective synthetic approach for the preparation of novel pyrimido[1,6-<i>a</i>]selenopheno[3,2-<i>d</i>]pyrimidine derivatives. The sequence involves the initial condensation of 3-amino-2,4-dicyano-5-(pyrrolidin-1-yl)selenophene <b>(1)</b> with 5-bromo-2,4-dichloro-6-methylpyrimidine <b>(2)</b>, followed by nucleophilic substitution with selected secondary amines. Subsequently, a base-induced intramolecular cyclization occurring on the nitrile group using NaNH<sub>2</sub> afforded the fused products <b>(6a–f)</b>. Although only a limited number of derivatives were obtained, this sequence offers a straightforward and modular route to fused heterocyclic systems. The structural features, including the disappearance of one nitrile group and the formation of the fused ring system, were characterized by FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, HMBC, and 2D NOESY analyses. The obtained data were consistent with the proposed structures and supported the formation of the fused pyrimidine–selenophene framework. This catalyst-free and operationally simple procedure highlights a practical synthetic pathway to selenium-containing fused pyrimidines, which have been previously difficult to access. Furthermore, preliminary antibacterial evaluation indicates promising biological potential for the obtained compounds.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1268-1277"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662719","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}
引用次数: 0
A Solvent-Free Synthesis of Imidazo[1,5-a]pyridines Using CCl4 as an Oxidant 以CCl4为氧化剂无溶剂合成咪唑[1,5- A]吡啶
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-24 DOI: 10.1002/jhet.70213
Alejandro Castillo-Baltazar, Luis E. Mendoza-Herrera, Alfredo Toscano, J. Armando Luján-Montelongo, M. Carmen Ortega-Alfaro, José G. López-Cortés
{"title":"A Solvent-Free Synthesis of Imidazo[1,5-a]pyridines Using CCl4 as an Oxidant","authors":"Alejandro Castillo-Baltazar,&nbsp;Luis E. Mendoza-Herrera,&nbsp;Alfredo Toscano,&nbsp;J. Armando Luján-Montelongo,&nbsp;M. Carmen Ortega-Alfaro,&nbsp;José G. López-Cortés","doi":"10.1002/jhet.70213","DOIUrl":"https://doi.org/10.1002/jhet.70213","url":null,"abstract":"<p>Imidazo[1,5-<i>a</i>]pyridines are intriguing molecules known for their unique biological and photophysical properties, making them valuable in medicinal chemistry. This study reports a solvent-free approach for synthesizing 3-arylimidazo[1,5-<i>a</i>]pyridines <b>1a-q</b> using carbon tetrachloride as an oxidant reagent and DBU as a base, affording good to high product yields. Based on control experiments, kinetic analysis conducted by <sup>13</sup>C NMR and DFT calculations, we propose a plausible reaction pathway to elucidate this transformation. Moreover, we demonstrate that CCl<sub>4</sub> is a chloride donor and oxidant by observing the formation of CHCl<sub>3</sub> as a byproduct.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1288-1299"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.70213","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662725","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}
引用次数: 0
2,4,6-Trichloro-1,3,5-Triazine: N,N-Dimethylformamide (TCT: DMF) Adduct as a Green Efficient Reagent for Synthetic Chemistry 2,4,6-三氯-1,3,5-三嗪：N，N-二甲基甲酰胺（TCT: DMF）加合物在合成化学中的绿色高效试剂
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-21 DOI: 10.1002/jhet.70211
Zunera Khalid, Munawar Ali Munawar, Rahila Huma, Syed Salman Shafqat, Hina Fatima Tahira, Nadeem Raza, Farooq Ahmad
{"title":"2,4,6-Trichloro-1,3,5-Triazine: N,N-Dimethylformamide (TCT: DMF) Adduct as a Green Efficient Reagent for Synthetic Chemistry","authors":"Zunera Khalid,&nbsp;Munawar Ali Munawar,&nbsp;Rahila Huma,&nbsp;Syed Salman Shafqat,&nbsp;Hina Fatima Tahira,&nbsp;Nadeem Raza,&nbsp;Farooq Ahmad","doi":"10.1002/jhet.70211","DOIUrl":"https://doi.org/10.1002/jhet.70211","url":null,"abstract":"<div>\u0000 \u0000 <p>TCT: DMF adduct is a unique, versatile, and emerging solid green reagent prepared by the combination of 2,4,6-trichloro-1,3,5-triazine and <i>N</i>,<i>N</i>-dimethylformamide. A key advantage of using TCT: DMF adduct as a catalyst is its ability to markedly shorten reaction time while achieving higher yields and selectivity. This review presents the first comprehensive literature highlighting the applications of TCT: DMF adduct as a catalyst under mild reaction conditions for various functional group transformations and heterocyclic syntheses. It is a Vilsmeier-like iminium electrophilic complex efficiently works as chlorinating, dehydrating, and formylating agent. The electron-deficient character of TCT: DMF adduct activates substrate in a short duration of time and substitution or nucleophilic attack of Cl<sup>−</sup> make it a valuable auxiliary for various synthetic reactions. It facilitates facile conversion of poor leaving groups like <span></span>OH, and <span></span>SO<sub>3</sub>H to their corresponding chlorides. The dehydrating property of this adduct enables the room temperature conversion of ketones to ketoximes and primary amines to nitriles. TCT: DMF actively participates in formylation and transesterification reactions. It has been established as best alternative of harsh and expensive reagents like SOCl<sub>2</sub> and POCl<sub>3</sub>/DMF. In heterocyclic synthesis, it serves as a key reagent for the synthesis of 2-azetidinones, quinolones, 3,4-dihydropyrimidinones/thiones, chromones, flavones, and isoflavones. Moreover, this review covers all catalytic activities of TCT: DMF adduct along with their reaction conditions and mechanisms that may be beneficial for various researchers.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1244-1267"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662749","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}
引用次数: 0
First Total Synthesis and Structural Elucidation of Microcystbiopterin C, a Pterin Glycoside From a Microcystis Bloom 微囊藻中蝶呤苷微囊生物terin C的首次全合成和结构解析
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-22 DOI: 10.1002/jhet.70214
Tadashi Hanaya, Katsuya Iwasaki
{"title":"First Total Synthesis and Structural Elucidation of Microcystbiopterin C, a Pterin Glycoside From a Microcystis Bloom","authors":"Tadashi Hanaya,&nbsp;Katsuya Iwasaki","doi":"10.1002/jhet.70214","DOIUrl":"https://doi.org/10.1002/jhet.70214","url":null,"abstract":"<div>\u0000 \u0000 <p>The first total synthesis and unambiguous structural elucidation of microcystbiopterin C, a pterin glycoside isolated from a <i>Microcystis</i> bloom, has been achieved. Two candidate biopterin glycosides (<b>5a</b> and <b>5b</b>) corresponding to the proposed structures of microcystbiopterin C were synthesized by glycosylation of a suitably protected biopterin derivative <b>10</b> with 2,4-di-<i>O</i>-benzoyl-6-deoxy-3-<i>O</i>-methyl-α-L-mannopyranosyl bromide (<b>9</b>) and the corresponding α-D-mannopyranosyl bromide (<b>22</b>), respectively, followed by stepwise deprotection. Detailed comparison of the NMR data and the specific rotation of compounds <b>5a</b> and <b>5b</b> with those of the natural product established that microcystbiopterin C possesses the structure of 2′-<i>O</i>-(6-deoxy-3-<i>O</i>-methyl-α-D-mannopyranosyl)biopterin (<b>5b</b>).</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1278-1287"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662581","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}
引用次数: 0
2,4,6-Trichloro-1,3,5-Triazine: N,N-Dimethylformamide (TCT: DMF) Adduct as a Green Efficient Reagent for Synthetic Chemistry 2,4,6-三氯-1,3,5-三嗪：N，N-二甲基甲酰胺（TCT: DMF）加合物在合成化学中的绿色高效试剂
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-21 DOI: 10.1002/jhet.70211
Zunera Khalid, Munawar Ali Munawar, Rahila Huma, Syed Salman Shafqat, Hina Fatima Tahira, Nadeem Raza, Farooq Ahmad
{"title":"2,4,6-Trichloro-1,3,5-Triazine: N,N-Dimethylformamide (TCT: DMF) Adduct as a Green Efficient Reagent for Synthetic Chemistry","authors":"Zunera Khalid,&nbsp;Munawar Ali Munawar,&nbsp;Rahila Huma,&nbsp;Syed Salman Shafqat,&nbsp;Hina Fatima Tahira,&nbsp;Nadeem Raza,&nbsp;Farooq Ahmad","doi":"10.1002/jhet.70211","DOIUrl":"https://doi.org/10.1002/jhet.70211","url":null,"abstract":"<div>\u0000 \u0000 <p>TCT: DMF adduct is a unique, versatile, and emerging solid green reagent prepared by the combination of 2,4,6-trichloro-1,3,5-triazine and <i>N</i>,<i>N</i>-dimethylformamide. A key advantage of using TCT: DMF adduct as a catalyst is its ability to markedly shorten reaction time while achieving higher yields and selectivity. This review presents the first comprehensive literature highlighting the applications of TCT: DMF adduct as a catalyst under mild reaction conditions for various functional group transformations and heterocyclic syntheses. It is a Vilsmeier-like iminium electrophilic complex efficiently works as chlorinating, dehydrating, and formylating agent. The electron-deficient character of TCT: DMF adduct activates substrate in a short duration of time and substitution or nucleophilic attack of Cl<sup>−</sup> make it a valuable auxiliary for various synthetic reactions. It facilitates facile conversion of poor leaving groups like <span></span>OH, and <span></span>SO<sub>3</sub>H to their corresponding chlorides. The dehydrating property of this adduct enables the room temperature conversion of ketones to ketoximes and primary amines to nitriles. TCT: DMF actively participates in formylation and transesterification reactions. It has been established as best alternative of harsh and expensive reagents like SOCl<sub>2</sub> and POCl<sub>3</sub>/DMF. In heterocyclic synthesis, it serves as a key reagent for the synthesis of 2-azetidinones, quinolones, 3,4-dihydropyrimidinones/thiones, chromones, flavones, and isoflavones. Moreover, this review covers all catalytic activities of TCT: DMF adduct along with their reaction conditions and mechanisms that may be beneficial for various researchers.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1244-1267"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662721","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}
引用次数: 0
Two-Step Ring-Transformation Strategy Toward Allomaltol Containing Pyrazolo[1,5-a][1,3,5]Triazine-2,4-Diones From Pyrano[2,3-f]Pyrazolo[3,4-d][1,3]Oxazepines via Urea Intermediates 尿素中间体催化吡唑啉[2,3-f]吡唑啉[3,4-d][1,3]恶氮平合成含吡唑啉[1,5-a][1,3,5]三嗪-2,4-二酮的二步法环转化策略
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-25 DOI: 10.1002/jhet.70215
Milena R. Garbuzova, Constantine V. Milyutin, Andrey N. Komogortsev
{"title":"Two-Step Ring-Transformation Strategy Toward Allomaltol Containing Pyrazolo[1,5-a][1,3,5]Triazine-2,4-Diones From Pyrano[2,3-f]Pyrazolo[3,4-d][1,3]Oxazepines via Urea Intermediates","authors":"Milena R. Garbuzova,&nbsp;Constantine V. Milyutin,&nbsp;Andrey N. Komogortsev","doi":"10.1002/jhet.70215","DOIUrl":"https://doi.org/10.1002/jhet.70215","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel two-step approach to previously unexplored allomaltol-containing pyrazolo[1,5-<i>a</i>][1,3,5]triazine-2,4-diones has been developed. The method involves the use of fused 1,3-oxazepin-2-one derivatives as precursors, which undergo C<span></span>O bond cleavage of the carbamate fragment upon treatment with amines, leading to the formation of substituted ureas. Subsequent condensation of these intermediates with 1,1′-carbonyldiimidazole provides access to the target bicyclic systems. This methodology employs readily available starting materials and proceeds under mild conditions, offering a straightforward protocol with simple product isolation that does not require chromatographic purification. The generality of this approach was demonstrated by the synthesis of 13 urea intermediates and 11 target heterocycles in yields of up to 78%. The structure of one representative product was confirmed by X-ray analysis.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1300-1312"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662814","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}
引用次数: 0
Two-Step Ring-Transformation Strategy Toward Allomaltol Containing Pyrazolo[1,5-a][1,3,5]Triazine-2,4-Diones From Pyrano[2,3-f]Pyrazolo[3,4-d][1,3]Oxazepines via Urea Intermediates 尿素中间体催化吡唑啉[2,3-f]吡唑啉[3,4-d][1,3]恶氮平合成含吡唑啉[1,5-a][1,3,5]三嗪-2,4-二酮的二步法环转化策略
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-25 DOI: 10.1002/jhet.70215
Milena R. Garbuzova, Constantine V. Milyutin, Andrey N. Komogortsev
{"title":"Two-Step Ring-Transformation Strategy Toward Allomaltol Containing Pyrazolo[1,5-a][1,3,5]Triazine-2,4-Diones From Pyrano[2,3-f]Pyrazolo[3,4-d][1,3]Oxazepines via Urea Intermediates","authors":"Milena R. Garbuzova,&nbsp;Constantine V. Milyutin,&nbsp;Andrey N. Komogortsev","doi":"10.1002/jhet.70215","DOIUrl":"https://doi.org/10.1002/jhet.70215","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel two-step approach to previously unexplored allomaltol-containing pyrazolo[1,5-<i>a</i>][1,3,5]triazine-2,4-diones has been developed. The method involves the use of fused 1,3-oxazepin-2-one derivatives as precursors, which undergo C<span></span>O bond cleavage of the carbamate fragment upon treatment with amines, leading to the formation of substituted ureas. Subsequent condensation of these intermediates with 1,1′-carbonyldiimidazole provides access to the target bicyclic systems. This methodology employs readily available starting materials and proceeds under mild conditions, offering a straightforward protocol with simple product isolation that does not require chromatographic purification. The generality of this approach was demonstrated by the synthesis of 13 urea intermediates and 11 target heterocycles in yields of up to 78%. The structure of one representative product was confirmed by X-ray analysis.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1300-1312"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662623","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}
引用次数: 0
A Solvent-Free Synthesis of Imidazo[1,5-a]pyridines Using CCl4 as an Oxidant 以CCl4为氧化剂无溶剂合成咪唑[1,5- A]吡啶
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-08-03 Epub Date: 2026-05-24 DOI: 10.1002/jhet.70213
Alejandro Castillo-Baltazar, Luis E. Mendoza-Herrera, Alfredo Toscano, J. Armando Luján-Montelongo, M. Carmen Ortega-Alfaro, José G. López-Cortés
{"title":"A Solvent-Free Synthesis of Imidazo[1,5-a]pyridines Using CCl4 as an Oxidant","authors":"Alejandro Castillo-Baltazar,&nbsp;Luis E. Mendoza-Herrera,&nbsp;Alfredo Toscano,&nbsp;J. Armando Luján-Montelongo,&nbsp;M. Carmen Ortega-Alfaro,&nbsp;José G. López-Cortés","doi":"10.1002/jhet.70213","DOIUrl":"https://doi.org/10.1002/jhet.70213","url":null,"abstract":"<p>Imidazo[1,5-<i>a</i>]pyridines are intriguing molecules known for their unique biological and photophysical properties, making them valuable in medicinal chemistry. This study reports a solvent-free approach for synthesizing 3-arylimidazo[1,5-<i>a</i>]pyridines <b>1a-q</b> using carbon tetrachloride as an oxidant reagent and DBU as a base, affording good to high product yields. Based on control experiments, kinetic analysis conducted by <sup>13</sup>C NMR and DFT calculations, we propose a plausible reaction pathway to elucidate this transformation. Moreover, we demonstrate that CCl<sub>4</sub> is a chloride donor and oxidant by observing the formation of CHCl<sub>3</sub> as a byproduct.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 8","pages":"1288-1299"},"PeriodicalIF":2.9,"publicationDate":"2026-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.70213","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148662908","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}
引用次数: 0
Green Synthesis and Biological Activity of Novel Imidazopyrimidine Employing Multicomponent Reaction of Thiourea 硫脲多组分反应绿色合成新型咪唑嘧啶及其生物活性研究
IF 2.9 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2026-07-13 Epub Date: 2026-04-28 DOI: 10.1002/jhet.70192
Mehrdad Ahmadian Kochaksaraei, Daryoush Zareyee, Mohammad A. Khalilzadeh, Zinatossadat Hossaini
{"title":"Green Synthesis and Biological Activity of Novel Imidazopyrimidine Employing Multicomponent Reaction of Thiourea","authors":"Mehrdad Ahmadian Kochaksaraei,&nbsp;Daryoush Zareyee,&nbsp;Mohammad A. Khalilzadeh,&nbsp;Zinatossadat Hossaini","doi":"10.1002/jhet.70192","DOIUrl":"https://doi.org/10.1002/jhet.70192","url":null,"abstract":"<div>\u0000 \u0000 <p>In this research, novel derivatives of imidazopyrimidine with a high level of efficiency were synthesized using Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>/CuO MNCs employing multicomponent reactions including vinylidene aldehydes, ethyl 2-amino-4-dioxo-4-arylbutanoates, alkyl bromides, thiourea, and ethyl bromopyruvate in water at room temperature. The produced compounds exhibit antioxidant activity as a result of the evaluation processes conducted on their NH group. Furthermore, an evaluation was performed on the antibacterial effectiveness of newly created pyridines using a disk diffusion technique, utilizing two different strains of Gram-negative bacteria. Significantly, the substances that were evaluated showed inhibitory effects on the development of Gram-positive bacteria as well. This method has several benefits, including quick response times, high product yields, and easy separation of catalyst and product using simple procedures.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 7","pages":"1145-1158"},"PeriodicalIF":2.9,"publicationDate":"2026-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148522853","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}
引用次数: 0
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