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Formaldehyde surrogates in multicomponent reactions.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-13 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.45
Cecilia I Attorresi, Javier A Ramírez, Bernhard Westermann
{"title":"Formaldehyde surrogates in multicomponent reactions.","authors":"Cecilia I Attorresi, Javier A Ramírez, Bernhard Westermann","doi":"10.3762/bjoc.21.45","DOIUrl":"10.3762/bjoc.21.45","url":null,"abstract":"<p><p>Formaldehyde emerges as a cornerstone in multicomponent reactions, mainly prized for its robust reactivity. Yet, alongside these beneficial traits, this highly reactive C1-building block raises concerns, primarily regarding its toxicity. One notable issue is the challenge of controlling the formation of undesired byproducts during its reactions. This review explores alternative C1-building blocks that serve as surrogates for formaldehyde, aiming to mitigate some of the challenges associated with its use in multicomponent reactions. By identifying these alternatives, toxicity concerns and improved reaction control can be addressed, paving the way for more efficient and sustainable synthetic methodologies.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"564-595"},"PeriodicalIF":2.2,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11912682/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143646971","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}
引用次数: 0
Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-13 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.44
Constantine V Milyutin, Andrey N Komogortsev, Boris V Lichitsky
{"title":"Study of the interaction of 2<i>H</i>-furo[3,2-<i>b</i>]pyran-2-ones with nitrogen-containing nucleophiles.","authors":"Constantine V Milyutin, Andrey N Komogortsev, Boris V Lichitsky","doi":"10.3762/bjoc.21.44","DOIUrl":"10.3762/bjoc.21.44","url":null,"abstract":"<p><p>For the first time, the reaction of substituted 2<i>H</i>-furo[3,2-<i>b</i>]pyran-2-ones with diverse <i>N</i>-nucleophiles was investigated. It was shown that the direction of the process depends on the type of employed nitrogen-containing reagent. For example, condensation with aliphatic amines leads to 2<i>H</i>-furo[3,2-<i>b</i>]pyran-2,7(3<i>H</i>)-diones bearing an exocyclic enamine moiety. At the same time, interaction with dinucleophiles results in recyclization accompanied by opening of the furan ring. Relied on the aforementioned process a general method for the synthesis of substituted pyrazol-3-ones with allomaltol fragment was designed. Structures of representatives of all obtained products were unambiguously confirmed by X-ray diffraction.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"556-563"},"PeriodicalIF":2.2,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11912642/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143647055","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}
引用次数: 0
Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-12 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.43
Yasushi Yoshida, Maho Aono, Takashi Mino, Masami Sakamoto
{"title":"Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt.","authors":"Yasushi Yoshida, Maho Aono, Takashi Mino, Masami Sakamoto","doi":"10.3762/bjoc.21.43","DOIUrl":"10.3762/bjoc.21.43","url":null,"abstract":"<p><p>β-Amino cyanoesters are important scaffolds because they can be transformed into useful chiral amines, amino acids, and amino alcohols. Halogen bonding, which can be formed between halogen atoms and electron-rich chemical species, is attractive because of its unique interaction in organic synthesis. Chiral halonium salts have been found to have strong halogen-bonding-donor abilities and work as powerful asymmetric catalysts. Recently, we have developed binaphthyl-based chiral halonium salts and applied them in several enantioselective reactions, which formed the corresponding products in high to excellent enantioselectivities. In this paper, the asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon stereogenic centers by the Mannich reaction through chiral halonium salt catalysis is presented, which provided the corresponding products in excellent yields with up to 86% ee. To the best of our knowledge, the present paper is the first to report the asymmetric construction of β-amino cyanoesters with contiguous tetrasubstituted carbon stereogenic centers by the catalytic Mannich reaction.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"547-555"},"PeriodicalIF":2.2,"publicationDate":"2025-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11912644/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143646967","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}
引用次数: 0
Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-10 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.41
Judit Hostalet-Romero, Laura Carceller-Ferrer, Gonzalo Blay, Amparo Sanz-Marco, José R Pedro, Carlos Vila
{"title":"Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates.","authors":"Judit Hostalet-Romero, Laura Carceller-Ferrer, Gonzalo Blay, Amparo Sanz-Marco, José R Pedro, Carlos Vila","doi":"10.3762/bjoc.21.41","DOIUrl":"10.3762/bjoc.21.41","url":null,"abstract":"<p><p>A valuable vinylogous addition reaction between 4-alkylidene-5-aminopyrazoles and alkyl trifluoropyruvates leading to highly functionalized tertiary alcohols bearing a trifluoromethyl group and a pyrazole ring is presented. The corresponding trifluoromethyl alcohols are obtained in moderate to good yields (up to 80%) and high diastereoselectivity (up to 7:1).</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"533-540"},"PeriodicalIF":2.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897652/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613166","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}
引用次数: 0
Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-10 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.42
Gianpaolo Gallo, Bartosz Lewandowski
{"title":"Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether.","authors":"Gianpaolo Gallo, Bartosz Lewandowski","doi":"10.3762/bjoc.21.42","DOIUrl":"10.3762/bjoc.21.42","url":null,"abstract":"<p><p>Tryptophan fulfills a plethora of important functions in nature both in its free form and as a component of peptides and proteins. Selective binding of tryptophan is therefore important for diagnostic and medicinal applications. Recently, we reported a glucose naphtho crown ether which is a chemoselective receptor for the esters of aromatic amino acids, in particular tryptophan, in water. Herein, we demonstrate that the same compound also binds free tryptophan selectively in aqueous media. Furthermore, it is capable of binding to tryptophan within model tripeptides. The naphthalene functionality in the glucose-derived receptor enables the study of guest binding using fluorescence spectroscopy.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"541-546"},"PeriodicalIF":2.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897655/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613184","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}
引用次数: 0
Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-07 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.39
Long K San, Sebastian Balser, Brian J Reeves, Tyler T Clikeman, Yu-Sheng Chen, Steven H Strauss, Olga V Boltalina
{"title":"Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene.","authors":"Long K San, Sebastian Balser, Brian J Reeves, Tyler T Clikeman, Yu-Sheng Chen, Steven H Strauss, Olga V Boltalina","doi":"10.3762/bjoc.21.39","DOIUrl":"10.3762/bjoc.21.39","url":null,"abstract":"<p><p>A new deep-blue emitting and highly fluorescent anthracene (ANTH) derivative containing perfluorobenzyl (Bn<sub>F</sub>) groups, 9,10-ANTH(Bn<sub>F</sub>)<sub>2</sub>, was synthesized in a single step reaction of ANTH or ANTH(Br)<sub>2</sub> with Bn<sub>F</sub>I, using either a high-temperature Cu-/Na<sub>2</sub>S<sub>2</sub>O<sub>3</sub>-promoted reaction or via a room-temperature photochemical reaction. Its structure was elucidated by NMR spectroscopy and single crystal X-ray diffractometry. The latter revealed no π-π interaction between neighboring ANTH cores. A combination of high photoluminescence quantum yield (PLQY) of 0.85 for 9,10-ANTH(Bn<sub>F</sub>)<sub>2</sub>, its significantly improved photostability compared to ANTH and 9,10-ANTH derivatives, and a simple synthetic access makes it an attractive material as a deep-blue OLED emitter and an efficient fluorescent probe.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"515-525"},"PeriodicalIF":2.2,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897650/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613192","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}
引用次数: 0
Cryptophycin unit B analogues.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-07 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.40
Thomas Schachtsiek, Jona Voss, Maren Hamsen, Beate Neumann, Hans-Georg Stammler, Norbert Sewald
{"title":"Cryptophycin unit B analogues.","authors":"Thomas Schachtsiek, Jona Voss, Maren Hamsen, Beate Neumann, Hans-Georg Stammler, Norbert Sewald","doi":"10.3762/bjoc.21.40","DOIUrl":"10.3762/bjoc.21.40","url":null,"abstract":"<p><p>Drug conjugates using toxic payloads are a promising approach for selectively combating cancer while sparing healthy tissue. The lack of highly cytotoxic and at the same time selective therapeutics against cancer is an ongoing challenge. Cryptophycins are a class of cyclic depsipeptides renowned for their high cytotoxicity in the picomolar range often combined with efficacy against multidrug-resistant tumour cell lines. However, cryptophycins failed as stand-alone drugs in cancer treatment, and their naturally occurring derivatives lack a covalent attachment handle. By making use of drug conjugates, toxic payloads such as cryptophycins can be selectively delivered to the target site. We present the synthesis of two conjugable cryptophycins with amino groups in unit B, representing potential payloads for drug conjugates particularly effective against multidrug-resistant cancers.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"526-532"},"PeriodicalIF":2.2,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897651/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613188","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}
引用次数: 0
Synthesis of the aggregation pheromone of Tribolium castaneum.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-06 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.38
Biyu An, Xueyang Wang, Ao Jiao, Qinghua Bian, Jiangchun Zhong
{"title":"Synthesis of the aggregation pheromone of <i>Tribolium castaneum</i>.","authors":"Biyu An, Xueyang Wang, Ao Jiao, Qinghua Bian, Jiangchun Zhong","doi":"10.3762/bjoc.21.38","DOIUrl":"10.3762/bjoc.21.38","url":null,"abstract":"<p><p><i>Tribolium castaneum</i> Herbst is a destructive stored product pest. The aggregation pheromone of this pest was prepared via a new and effective strategy. The key steps include the ring-opening reaction of chiral 2-methyloxirane, the stereospecific inversion of chiral secondary tosylate, Li<sub>2</sub>CuCl<sub>4</sub>-catalyzed coupling of tosylate with Grignard reagent, and oxidation with RuCl<sub>3</sub>/NaIO<sub>4.</sub></p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"510-514"},"PeriodicalIF":2.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897649/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613201","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}
引用次数: 0
Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-05 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.37
Metodej Dvoracek, Brendan Twamley, Mathias O Senge, Mikhail A Filatov
{"title":"Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye.","authors":"Metodej Dvoracek, Brendan Twamley, Mathias O Senge, Mikhail A Filatov","doi":"10.3762/bjoc.21.37","DOIUrl":"10.3762/bjoc.21.37","url":null,"abstract":"<p><p>Bimanes, a class of molecules based on the 1<i>H</i>,7<i>H</i>-pyrazolo[1,2-<i>a</i>]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1<i>H</i>,7<i>H</i>-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (<b>Cl</b> <b><sub>2</sub></b> <b>B</b>), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"500-509"},"PeriodicalIF":2.2,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897657/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613144","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}
引用次数: 0
Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.35
Laurin Flemmich, Ronald Micura
{"title":"Synthesis of electrophile-tethered preQ<sub>1</sub> analogs for covalent attachment to preQ<sub>1</sub> RNA.","authors":"Laurin Flemmich, Ronald Micura","doi":"10.3762/bjoc.21.35","DOIUrl":"10.3762/bjoc.21.35","url":null,"abstract":"<p><p>The preQ<sub>1</sub> cIass-I riboswitch aptamer can utilize 7-aminomethyl-7-deazaguanine (preQ<sub>1</sub>) ligands that are equipped with an electrophilic handle for the covalent attachment of the ligand to the RNA. The simplicity of the underlying design of irreversibly bound ligand-RNA complexes has provided a new impetus in the fields of covalent RNA labeling and RNA drugging. Here, we present short and robust synthetic routes for such reactive preQ<sub>1</sub> and (2,6-diamino-7-aminomethyl-7-deazapurine) DPQ<sub>1</sub> ligands. The readily accessible key intermediates of preQ<sub>0</sub> and DPQ<sub>0</sub> (both bearing a nitrile moiety instead of the aminomethyl group) were reduced to the corresponding 7-formyl-7-deazapurine counterparts. These readily undergo reductive amination to form the hydroxyalkyl handles, which were further converted to the haloalkyl or mesyloxyalkyl-modified target compounds. In addition, we report hydrogenation conditions for preQ<sub>0</sub> and DPQ<sub>0</sub> that allow for cleaner and faster access to preQ<sub>1</sub> compared to existing routes and provide the novel compound DPQ<sub>1</sub>.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"483-489"},"PeriodicalIF":2.2,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897656/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613200","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}
引用次数: 0
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