Pub Date : 2024-08-13DOI: 10.24820/ark.5550190.p012.214
Gamal A. El‐Hiti, Bakr F. Abdel-Wahab, H. Mohamed, Ehab M. Zayed, B. Kariuki
{"title":"Bromination of (E)-1-(5-methyl-1-(aryl)-1H-1,2,3-triazol-4-yl)-3-arylprop-2-en-1-ones using N-bromosuccinimide under acidic conditions","authors":"Gamal A. El‐Hiti, Bakr F. Abdel-Wahab, H. Mohamed, Ehab M. Zayed, B. Kariuki","doi":"10.24820/ark.5550190.p012.214","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.214","url":null,"abstract":"","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141919524","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}
Pub Date : 2024-08-13DOI: 10.24820/ark.5550190.p012.214
Gamal A. El‐Hiti, Bakr F. Abdel-Wahab, H. Mohamed, Ehab M. Zayed, B. Kariuki
{"title":"Bromination of (E)-1-(5-methyl-1-(aryl)-1H-1,2,3-triazol-4-yl)-3-arylprop-2-en-1-ones using N-bromosuccinimide under acidic conditions","authors":"Gamal A. El‐Hiti, Bakr F. Abdel-Wahab, H. Mohamed, Ehab M. Zayed, B. Kariuki","doi":"10.24820/ark.5550190.p012.214","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.214","url":null,"abstract":"","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141919077","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}
Pub Date : 2024-07-27DOI: 10.24820/ark.5550190.p012.151
R. Dandela, Dattatray Gaikwad, Rana Chatterjee, Sujeet A. Gaware, Achyuta Nanda Acharya
An alternate synthetic approach has been described to access novel apixaban analogues. The present strategy offers a practical and cost-effective synthetic procedure to construct the privileged scaffold and its amide derivatives that may exhibit promising anticoagulant potency. Moreover, the method was performed by using less expensive reagents, easily achievable precursors
{"title":"An alternative synthetic strategy to construct apixaban analogues","authors":"R. Dandela, Dattatray Gaikwad, Rana Chatterjee, Sujeet A. Gaware, Achyuta Nanda Acharya","doi":"10.24820/ark.5550190.p012.151","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.151","url":null,"abstract":"An alternate synthetic approach has been described to access novel apixaban analogues. The present strategy offers a practical and cost-effective synthetic procedure to construct the privileged scaffold and its amide derivatives that may exhibit promising anticoagulant potency. Moreover, the method was performed by using less expensive reagents, easily achievable precursors","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141797200","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}
Pub Date : 2024-07-14DOI: 10.24820/ark.5550190.p012.223
Rosa M. Claramunt, D. Sanz, J. Elguero, I. Alkorta
{"title":"Pyrazolidines: synthesis, reactivity, physical and biological properties","authors":"Rosa M. Claramunt, D. Sanz, J. Elguero, I. Alkorta","doi":"10.24820/ark.5550190.p012.223","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.223","url":null,"abstract":"","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141649886","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 novel concise and convergent approach for the preparation of bempedoic acid, a new group of non-statin LDL-lowering drug has been developed starting from pentane-1,5-diol in 8 steps with an overall yield of 20%. Result: The synthesis of a key precursor i.e. 1,11-dihydroxyundecan-6-one, has been accomplished through the ring opening of - caprolactone with alkyl Grignard reagent. This method doesn’t require the use of p - toluenesulfonylmethylisocyanaide (TosMIC) for the construction of dihyroxyketone, a key intermediate of bempedoic acid. The key steps involved in this approach are the bromination of dihydroxyketone and base-catalyzed alkylation of methyl isobutyrate with 1,11-dibromoundecan-6-ol followed by the hydrolysis of dimethyl ester into bempedoic acid.
{"title":"TosMIC-free synthesis of bempedoic acid, a hypercholesterolemia drug","authors":"B.V. Subba reddy, Rachel Gundamalla, Rajashaker Bantu","doi":"10.24820/ark.5550190.p012.204","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.204","url":null,"abstract":"A novel concise and convergent approach for the preparation of bempedoic acid, a new group of non-statin LDL-lowering drug has been developed starting from pentane-1,5-diol in 8 steps with an overall yield of 20%. Result: The synthesis of a key precursor i.e. 1,11-dihydroxyundecan-6-one, has been accomplished through the ring opening of - caprolactone with alkyl Grignard reagent. This method doesn’t require the use of p - toluenesulfonylmethylisocyanaide (TosMIC) for the construction of dihyroxyketone, a key intermediate of bempedoic acid. The key steps involved in this approach are the bromination of dihydroxyketone and base-catalyzed alkylation of methyl isobutyrate with 1,11-dibromoundecan-6-ol followed by the hydrolysis of dimethyl ester into bempedoic acid.","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141654644","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}
Pub Date : 2024-07-11DOI: 10.24820/ark.5550190.p012.219
M. Anary‐Abbasinejad, Maryam Oudi
An effective protocol for synthesis of some new pyrazolone-substituted C-acylimine derivatives is reported through a one-pot three-component reaction between arylglyoxals, aniline derivatives and pyrazolone. All reactions were conducted in ethanol/acetic acid mixture as solvent and the stable products were obtained by simple filtering off the precipitated solids in high yields. The structures of all products were proved by 1 H and 13 C NMR and IR spectral and elemental analysis data
通过芳基乙二醛、苯胺衍生物和吡唑酮之间的单锅三组分反应，报告了合成一些新的吡唑酮取代的 C-酰亚胺衍生物的有效方案。所有反应均在乙醇/乙酸混合溶剂中进行，只需过滤掉沉淀的固体，即可获得稳定的高产率产物。所有产物的结构均通过 1 H 和 13 C NMR、IR 光谱和元素分析数据得到证实。
{"title":"An efficient synthesis of new pyrazolone-substituted C-acylimine derivatives by three-component reaction between arylglyoxal derivatives, arylamines and pyrazolone","authors":"M. Anary‐Abbasinejad, Maryam Oudi","doi":"10.24820/ark.5550190.p012.219","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.219","url":null,"abstract":"An effective protocol for synthesis of some new pyrazolone-substituted C-acylimine derivatives is reported through a one-pot three-component reaction between arylglyoxals, aniline derivatives and pyrazolone. All reactions were conducted in ethanol/acetic acid mixture as solvent and the stable products were obtained by simple filtering off the precipitated solids in high yields. The structures of all products were proved by 1 H and 13 C NMR and IR spectral and elemental analysis data","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141657586","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}
Pub Date : 2024-07-06DOI: 10.24820/ark.5550190.p012.217
M. Planas, Gerard Riesco-Llach, L. Feliu, J. Joule
3-Oxidopyraziniums are accessed from 2(1 H )-pyrazinones via N-alkylation and then exposure of the resulting pyrazinium salts to mild base at room temperature. 3-Oxidopyraziniums react with acrylates in a 1,3-dipolar cyclisation producing 3,8-diazabicyclo[3.2.1]octanes. 3-Oxido-1-(4-methoxybenzyl)-5,6-dimethylpyrazinium (C 14 H 16 N 2 O 2 ) dimerises at room temperature, forming a tetracyclic alcohol C 28 H 34 N 4 O 5 , the structure of which was elucidated using spectroscopic and X-ray analyses.
3-Oxidopyraziniums 是通过 N- 烷基化作用从 2(1 H )- 吡嗪酮中获得的，然后在室温下将生成的吡嗪盐暴露于弱碱中。3-Oxidopyraziniums 与丙烯酸酯发生 1,3-二极环化反应，生成 3,8-二氮杂双环[3.2.1]辛烷。3- 氧代-1-（4-甲氧基苄基）-5,6-二甲基吡嗪鎓（C 14 H 16 N 2 O 2 ）在室温下发生二聚反应，形成四环醇 C 28 H 34 N 4 O 5，其结构通过光谱和 X 射线分析得以阐明。
{"title":"The cycloaddition chemistry of 3-oxidopyraziniums. Dimerisation of 3-oxido-1-(4-methoxybenzyl)-5,6-dimethylpyrazinium","authors":"M. Planas, Gerard Riesco-Llach, L. Feliu, J. Joule","doi":"10.24820/ark.5550190.p012.217","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.217","url":null,"abstract":"3-Oxidopyraziniums are accessed from 2(1 H )-pyrazinones via N-alkylation and then exposure of the resulting pyrazinium salts to mild base at room temperature. 3-Oxidopyraziniums react with acrylates in a 1,3-dipolar cyclisation producing 3,8-diazabicyclo[3.2.1]octanes. 3-Oxido-1-(4-methoxybenzyl)-5,6-dimethylpyrazinium (C 14 H 16 N 2 O 2 ) dimerises at room temperature, forming a tetracyclic alcohol C 28 H 34 N 4 O 5 , the structure of which was elucidated using spectroscopic and X-ray analyses.","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141672216","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}
Pub Date : 2024-07-06DOI: 10.24820/ark.5550190.p012.213
V. Zhdankin, A. Yoshimura, Kim Ngo, I. Mironova, Zachary S. Gardner, Nami Ogura, Akiharu Ueki, M. Yusubov, Akio Saito
Mesityl benziodoxaborole triflate is a unique benzyne precursor under aqueous conditions in the presence of NaHCO 3 at room temperature. Reactions of alkyl aryl sulfides with benzyne generated under these conditions selectively afford the corresponding sulfonium salts. In contrast, the previously reported reactions of alkyl aryl sulfides with common benzyne precursors under strongly basic anhydrous conditions lead to various products of cyclization, rearrangement
{"title":"Generation of Benzyne from Aryl Benziodoxaborole Triflate under Aqueous Conditions and its Reactions with Alkyl Aryl Sulfides","authors":"V. Zhdankin, A. Yoshimura, Kim Ngo, I. Mironova, Zachary S. Gardner, Nami Ogura, Akiharu Ueki, M. Yusubov, Akio Saito","doi":"10.24820/ark.5550190.p012.213","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.213","url":null,"abstract":"Mesityl benziodoxaborole triflate is a unique benzyne precursor under aqueous conditions in the presence of NaHCO 3 at room temperature. Reactions of alkyl aryl sulfides with benzyne generated under these conditions selectively afford the corresponding sulfonium salts. In contrast, the previously reported reactions of alkyl aryl sulfides with common benzyne precursors under strongly basic anhydrous conditions lead to various products of cyclization, rearrangement","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141671990","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}
Pub Date : 2024-07-06DOI: 10.24820/ark.5550190.p012.224
Christopher A. Ramsden, W. P. Oziminski
The properties of heterocyclic mesomeric betaines (HMBs) are determined by the connectivity between the ring 2 π heteroatoms and the odd conjugated fragments that complete the ring. In contrast to conjugated HMBs (1,3-dipoles) and cross-conjugated HMBs (1,4-dipoles), semi-conjugated HMBs are a class of heterocycle that is unexplored. The only known example is 1,4-dimethyl-1,2,4,5-tetrazinium-3,6-diolate. In this study density functional theory (DFT) methodology is employed to further investigate the structures and properties of examples of mono- bi-and tricyclic semi-conjugated HMBs. A common feature associated with the ‘semi - conjugation’ is a small energy gap between the frontier orbitals
{"title":"A DFT Study of Mono-, Bi- and Tricyclic Examples of \u0000Semi-conjugated Heterocyclic Mesomeric Betaines","authors":"Christopher A. Ramsden, W. P. Oziminski","doi":"10.24820/ark.5550190.p012.224","DOIUrl":"https://doi.org/10.24820/ark.5550190.p012.224","url":null,"abstract":"The properties of heterocyclic mesomeric betaines (HMBs) are determined by the connectivity between the ring 2 π heteroatoms and the odd conjugated fragments that complete the ring. In contrast to conjugated HMBs (1,3-dipoles) and cross-conjugated HMBs (1,4-dipoles), semi-conjugated HMBs are a class of heterocycle that is unexplored. The only known example is 1,4-dimethyl-1,2,4,5-tetrazinium-3,6-diolate. In this study density functional theory (DFT) methodology is employed to further investigate the structures and properties of examples of mono- bi-and tricyclic semi-conjugated HMBs. A common feature associated with the ‘semi - conjugation’ is a small energy gap between the frontier orbitals","PeriodicalId":8432,"journal":{"name":"Arkivoc","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141671517","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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