Homoconjugated push–pull chromophores were obtained by an efficient, click-type formal [2+2] cycloadditions. With these short synthetic transformations, complex chromophore structures were achieved in a single step without any by-product formation. Significant second-order optical nonlinearities have been calculated for the synthesized compounds.
{"title":"Click-Type Synthesis of Homoconjugated Push–Pull Chromophores: Computational Investigation of Optical and Nonlinear Optical (NLO) Properties","authors":"Fevzi Can Inyurt, F. Mammadova, Çağatay Dengiz","doi":"10.1055/a-2004-6344","DOIUrl":"https://doi.org/10.1055/a-2004-6344","url":null,"abstract":"Homoconjugated push–pull chromophores were obtained by an efficient, click-type formal [2+2] cycloadditions. With these short synthetic transformations, complex chromophore structures were achieved in a single step without any by-product formation. Significant second-order optical nonlinearities have been calculated for the synthesized compounds.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"1 - 7"},"PeriodicalIF":2.5,"publicationDate":"2022-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45798614","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. Burke, Silvia Spiccio, M. D. Di Filippo, M. Baumann
Pyrazolines and their pyrazole congeners are important heterocyclic building blocks with numerous applications in the fine chemical industries. However, traditional routes towards these entities are based on multistep syntheses generating substantial amounts of chemical waste. Here we report an alternative approach using UV-light to convert tetrazoles to pyrazolines via a reagent-free photo-click strategy. This route generates nitrile imine dipoles in situ that are trapped with different dipolarophiles rendering a selection of these heterocyclic targets in high chemical yields. A continuous flow method is ultimately realized that generates multi-gram quantities of product in a safe and readily scalable manner thus demonstrating the value of this photochemical approach for future exploitations in industry.
{"title":"Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow","authors":"A. Burke, Silvia Spiccio, M. D. Di Filippo, M. Baumann","doi":"10.1055/a-1995-1859","DOIUrl":"https://doi.org/10.1055/a-1995-1859","url":null,"abstract":"Pyrazolines and their pyrazole congeners are important heterocyclic building blocks with numerous applications in the fine chemical industries. However, traditional routes towards these entities are based on multistep syntheses generating substantial amounts of chemical waste. Here we report an alternative approach using UV-light to convert tetrazoles to pyrazolines via a reagent-free photo-click strategy. This route generates nitrile imine dipoles in situ that are trapped with different dipolarophiles rendering a selection of \u0000these heterocyclic targets in high chemical yields. A continuous flow method is ultimately realized that generates multi-gram quantities of product in a safe and readily scalable manner thus demonstrating the value of this photochemical approach for future exploitations in industry.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"69 - 75"},"PeriodicalIF":2.5,"publicationDate":"2022-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41701632","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Maria Edith Casacchia, G. Giorgianni, E. Allegritti, L. Giansanti, Armando Carlone, Fabio Pesciaioli
The development of micellar catalysis offers a sustainable alternative to organic solvents representing an environmental milestone in organic synthesis. Here the first Michael addition of masked acetaldehyde under neutral, cationic and anionic micellar catalysis is reported, affording the products in high yields and enantiomeric excess in spite the use of water as solvent.
{"title":"Organocatalytic Synthesis of γ-Amino Acid Precursors via Masked Acetaldehyde under Micellar Catalysis","authors":"Maria Edith Casacchia, G. Giorgianni, E. Allegritti, L. Giansanti, Armando Carlone, Fabio Pesciaioli","doi":"10.1055/a-1996-8940","DOIUrl":"https://doi.org/10.1055/a-1996-8940","url":null,"abstract":"The development of micellar catalysis offers a sustainable alternative to organic solvents representing an environmental milestone in organic synthesis. Here the first Michael addition of masked acetaldehyde under neutral, cationic and anionic micellar catalysis is reported, affording the products in high yields and enantiomeric excess in spite the use of water as solvent.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"29 - 32"},"PeriodicalIF":2.5,"publicationDate":"2022-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49430670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
P. Mallesham, K. Raghavulu, Venkatesh Miriyala, Raju Doddipalla, Satyanarayana Yennam, P. Sanasi, M. Behera
The paper describes the efficient total syntheses of naturally occurring tripeptides Acidiphilamides A–C and epi-Acidiphilamides A-C, which were prepared from commercially available L-phenyl alanine using Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium (HATU) as peptide coupling reagent. The structures of the natural Acidiphilamides A, B and C were characterized by NMR, MS & SOR data which were matching with those of natural products, whereas the structures of epi-Acidiphilamides A, B and C were confirmed by 2D NMR studies.
{"title":"Synthesis of Acidiphilamide A–C: Secondary Metabolites from the Genus Streptacidiphilus","authors":"P. Mallesham, K. Raghavulu, Venkatesh Miriyala, Raju Doddipalla, Satyanarayana Yennam, P. Sanasi, M. Behera","doi":"10.1055/a-2035-9753","DOIUrl":"https://doi.org/10.1055/a-2035-9753","url":null,"abstract":"The paper describes the efficient total syntheses of naturally occurring tripeptides Acidiphilamides A–C and epi-Acidiphilamides A-C, which were prepared from commercially available L-phenyl alanine using Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium (HATU) as peptide coupling reagent. The structures of the natural Acidiphilamides A, B and C were characterized by NMR, MS & SOR data which were matching with those of natural products, whereas the structures of epi-Acidiphilamides A, B and C were confirmed by 2D NMR studies.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"130 - 139"},"PeriodicalIF":2.5,"publicationDate":"2022-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44064262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shikha Jyoti Borah, Akanksha Gupta, P. Sahu, N. Dheer, Vinod Kumar
Pesticides are widely used to prevent bug infestation in agricultural crops and to get rid of other pests and disease-carrying creatures including mice, rats, ticks, and mosquitoes from various environment and h In response to this environmental and human health hazard, a dire need for remediation has emerged in the last few decades. Green approaches for the remediation of pesticides can boost sustainable development. A biomimetic approach for degradation of pesticides can have high potential to generate ripples of positive outcomes. Biomimetic catalysts are synthetic chemical molecules which have been inspired by natural processes to mimic their structural and functional properties. This short review concisely focuses on the synthesis of various biomimetic catalysts including metal-based materials, carbon-based materials and others. In this context, recent advances achieved by such biomimetic catalysts for the degradation of pesticides have been covered. It highlights the importance of adopting a biomimetic approach as it provides a green and efficient method for pesticides degradation
{"title":"Science through the Lens of Nature: Recent Advances in Biomimetic Approaches towards Pesticide Degradation","authors":"Shikha Jyoti Borah, Akanksha Gupta, P. Sahu, N. Dheer, Vinod Kumar","doi":"10.1055/a-2004-7289","DOIUrl":"https://doi.org/10.1055/a-2004-7289","url":null,"abstract":"Pesticides are widely used to prevent bug infestation in agricultural crops and to get rid of other pests and disease-carrying creatures including mice, rats, ticks, and mosquitoes from various environment and h In response to this environmental and human health hazard, a dire need for remediation has emerged in the last few decades. Green approaches for the remediation of pesticides can boost sustainable development. A biomimetic approach for degradation of pesticides can have high potential to generate ripples of positive outcomes. Biomimetic catalysts are synthetic chemical molecules which have been inspired by natural processes to mimic their structural and functional properties. This short review concisely focuses on the synthesis of various biomimetic catalysts including metal-based materials, carbon-based materials and others. In this context, recent advances achieved by such biomimetic catalysts for the degradation of pesticides have been covered. It highlights the importance of adopting a biomimetic approach as it provides a green and efficient method for pesticides degradation","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"33 - 42"},"PeriodicalIF":2.5,"publicationDate":"2022-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48953414","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The development of new pharmacologically active molecules targeting tubulin polymerization has recently attracted great interest in research groups. In efforts to develop new potent anticancer compounds, imidazole-tethered/fused pharmacologically active aryl derivatives possessing different substitution patterns targeting tubulin polymerization have been rationally designed and synthesized. The target molecules (P1-5 and KG1-5) were synthesized by multistep syntheses involving the reaction of intermediate 2-aminophenyl-tethered imidazoles with appropriate reactants in the presence of p-TsOH under different conditions. The synthesized compounds displayed moderate to good cytotoxicity, comparable to that of colchicine, against four cancer cell lines (MCF-7, MD-MBA-231, A549, and HCT-116). Compounds P2 and P5, with an imidazoloquinoxaline moiety, emerged as potential leads with cytotoxicity profiles against these cell lines similar to colchicine. Compounds P2 and P5 arrested cell division at the G2/M phase and prevented cancerous cell growth through induced apoptosis. These results favored the hypothesis that the compounds might act by binding to the colchicine binding site, which was further confirmed with the help of a tubulin polymerization inhibition assay. The results encourage the further exploration of imidazoloquinoxalines as promising leads that deserve advanced clinical investigation.
{"title":"Design, Synthesis and Biological Evaluation of Imidazole-Substituted/Fused Aryl Derivatives Targeting Tubulin Polymerization as Anticancer Agents","authors":"K. Goel, S. Rajput, Rajeev Kharb","doi":"10.1055/s-0042-1751835","DOIUrl":"https://doi.org/10.1055/s-0042-1751835","url":null,"abstract":"The development of new pharmacologically active molecules targeting tubulin polymerization has recently attracted great interest in research groups. In efforts to develop new potent anticancer compounds, imidazole-tethered/fused pharmacologically active aryl derivatives possessing different substitution patterns targeting tubulin polymerization have been rationally designed and synthesized. The target molecules (P1-5 and KG1-5) were synthesized by multistep syntheses involving the reaction of intermediate 2-aminophenyl-tethered imidazoles with appropriate reactants in the presence of p-TsOH under different conditions. The synthesized compounds displayed moderate to good cytotoxicity, comparable to that of colchicine, against four cancer cell lines (MCF-7, MD-MBA-231, A549, and HCT-116). Compounds P2 and P5, with an imidazoloquinoxaline moiety, emerged as potential leads with cytotoxicity profiles against these cell lines similar to colchicine. Compounds P2 and P5 arrested cell division at the G2/M phase and prevented cancerous cell growth through induced apoptosis. These results favored the hypothesis that the compounds might act by binding to the colchicine binding site, which was further confirmed with the help of a tubulin polymerization inhibition assay. The results encourage the further exploration of imidazoloquinoxalines as promising leads that deserve advanced clinical investigation.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"17 - 28"},"PeriodicalIF":2.5,"publicationDate":"2022-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44631179","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The sulfoximine based tetrazoles have been synthesized via Azido-Ugi four component reactions of sulfoximines, isocyanides, aldehydes, and TMS-azide in MeOH at 70 ℃ in the presence of InCl3. Replacement of sulfoximine with sulfonimidamide (SIA) have delivered corresponding SIA based tetrazole. Interestingly, SIA is also acting as a surrogate amine to accomplish corresponding aminotetrazole as by-product.
{"title":"Synthesis of α-Sulfoximino Tetrazoles via Azido-Ugi Four-Component Reaction","authors":"C. I. Jesin, R. Kataria, G. Nandi","doi":"10.1055/a-1981-9151","DOIUrl":"https://doi.org/10.1055/a-1981-9151","url":null,"abstract":"The sulfoximine based tetrazoles have been synthesized via Azido-Ugi four component reactions of sulfoximines, isocyanides, aldehydes, and TMS-azide in MeOH at 70 ℃ in the presence of InCl3. Replacement of sulfoximine with sulfonimidamide (SIA) have delivered corresponding SIA based tetrazole. Interestingly, SIA is also acting as a surrogate amine to accomplish corresponding aminotetrazole as by-product.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"06 1","pages":"319 - 328"},"PeriodicalIF":2.5,"publicationDate":"2022-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41999580","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. Narsaiah, D. Biradar, Y. Mane, Y. P. Sarnikar, S. G. Kulkarni, B. Reddy
An efficient approach for the one-pot synthesis of 4-bromotetrahydropyrans in a highly diastereoselective manner via the alkynylation followed by Prins cyclisation is described. The method employs aldehydes and allyl bromide as reactants, with a Zn/ZnBr2 catalytic system in CH2Cl2. A variety of 2,6-disubstituted 4-bromotetrahydropyran derivatives were obtained in good yields.
{"title":"Zn/ZnBr2 Catalysed Reaction of Aldehydes with Allylbromide: Synthesis of 2,6-Disubstituted 4-Bromotetrahydropyrans","authors":"A. Narsaiah, D. Biradar, Y. Mane, Y. P. Sarnikar, S. G. Kulkarni, B. Reddy","doi":"10.1055/s-0042-1751374","DOIUrl":"https://doi.org/10.1055/s-0042-1751374","url":null,"abstract":"An efficient approach for the one-pot synthesis of 4-bromotetrahydropyrans in a highly diastereoselective manner via the alkynylation followed by Prins cyclisation is described. The method employs aldehydes and allyl bromide as reactants, with a Zn/ZnBr2 catalytic system in CH2Cl2. A variety of 2,6-disubstituted 4-bromotetrahydropyran derivatives were obtained in good yields.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42620193","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Construction of all-carbon quaternary centres is an important task in organic synthesis. In spite of the challenges associated with the Csp3-Csp3 bond constructions in a sterically constrained environment, significant advances have been made in this area. Among the latter, catalytic and non-catalytic [3+2] cycloaddition approach has gained wide attention recently. This short review summarizes the [3+2] cycloaddition reactions reported during the period 2016-2022 for the synthesis of molecules possessing one or more all-carbon quaternary stereocentre
{"title":"Recent progress on the [3+2] cycloaddition route for the synthesis of all-carbon quaternary stereocentres","authors":"A. Deepthi, Maneesh Mohan, C. Meenakshy","doi":"10.1055/a-1947-3351","DOIUrl":"https://doi.org/10.1055/a-1947-3351","url":null,"abstract":"Construction of all-carbon quaternary centres is an important task in organic synthesis. In spite of the challenges associated with the Csp3-Csp3 bond constructions in a sterically constrained environment, significant advances have been made in this area. Among the latter, catalytic and non-catalytic [3+2] cycloaddition approach has gained wide attention recently. This short review summarizes the [3+2] cycloaddition reactions reported during the period 2016-2022 for the synthesis of molecules possessing one or more all-carbon quaternary stereocentre","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46870331","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The naturally abundant, enantiomerically pure cyclitol quinic acid (1) has been converted into the synthetically useful enone 2 in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, the readily derived α-iodoenone 3 participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones 2 and 3 are useful, enantiomerically pure building blocks for organic synthesis.
{"title":"Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid","authors":"Shen Tan, P. Lan, M. Banwell, L. V. White","doi":"10.1055/a-1952-4557","DOIUrl":"https://doi.org/10.1055/a-1952-4557","url":null,"abstract":"The naturally abundant, enantiomerically pure cyclitol quinic acid (1) has been converted into the synthetically useful enone 2 in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, the readily derived α-iodoenone 3 participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones 2 and 3 are useful, enantiomerically pure building blocks for organic synthesis.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"06 1","pages":"306 - 311"},"PeriodicalIF":2.5,"publicationDate":"2022-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49066720","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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