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A one-pot highly selective approach to the synthesis of hitherto unknown tetrahydropyrrolo[2',1':3,4]pyrazino[1,2-]pyrrolo[2',1':3,4]pyrazino[1,2-][1,2,4,5]tetrazine ensembles from simple and available -allenylpyrrole-2-carbaldehydes and hydrazines has been developed. The reaction proceeds in a very facile manner and tolerates different substituents in both pyrroles and hydrazines. The novel class of organic compounds, tetrahydrodipyrrolodipyrazinotetrazines, proves to be promising pH-sensitive switchers to deliver -aminopyrrolopyrazinium salts in acidic media and then again tetrahydrodipyrrolodipyrazinotetrazines in basic media. Both transformations give the products in quantitative yields.
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http://dx.doi.org/10.1021/acs.orglett.3c03751 | DOI Listing |
Angew Chem Int Ed Engl
September 2025
Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou, 310058, P.R. China.
Porous organic cages (POCs) have emerged as promising porous materials for a wide range of applications. However, their development is often limited by insufficient chemical stability and challenges in systematically functionalization. Herein, we reported the design and synthesis of a tetrazine-based POC (TC1) featuring rigid tetrahedral structure, prepared via a one-pot nucleophilic aromatic substitution reaction.
View Article and Find Full Text PDFACS Chem Biol
September 2025
Institute for Biomedicine and Glycomics, Griffith University, Queensland, 4111 Brisbane, Australia.
Small-molecule metabolic chemical probes are tailored chemical biology tools that are designed to detect and visualize biological processes within a cell or an organism. Nucleoside analogues are a subset of metabolic probes that enable the study of DNA synthesis, proliferation kinetics, and cell cycle progression. However, most available nucleoside analogue probes have been designed for use in mammalian cells, limiting their use in other species, where there are metabolic pathway differences.
View Article and Find Full Text PDFJ Org Chem
September 2025
College of Chemistry and Materials Science, Key Laboratory of Analytical Science and Technology of Hebei Province, and MOE Key Laboratory of Medicinal Chemistry and Molecular Diagnostics, Hebei University, Baoding 071002, Hebei, China.
In this work, the previously reported SeODR strategy was used successfully for the synthesis of bicyclic peptides (). with different rings bearing various thioether linkages were prepared through a one-pot reaction; 15 with satisfactory yields were achieved. Cross-linkers including xylylene dibromide (, 2,6-bis(bromomethyl)pyridine (, 4,4'-bis(bromomethyl)biphenyl (), 1,3-dichloroacetone (, and dichloro--tetrazine ( are all compatible with the SeODR approach used for deprotection of the S-acetamidomethyl (Acm) group in peptides.
View Article and Find Full Text PDFAdv Mater Interfaces
January 2025
Weldon School of Biomedical Engineering, Purdue University, West Lafayette, IN, USA.
Poly(ethylene glycol)-norbornene (e.g., PEGNB) is a versatile macromer amenable to step-growth thiol-norbornene photopolymerization and inverse electron demand Diels-Alder (iEDDA) click reaction.
View Article and Find Full Text PDFAnal Chem
September 2025
School of Chemistry, Key Laboratory of Advanced Technologies of Material, Ministry of Education, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, People's Republic of China.
Photoactive probes are important derivatives of small molecule fluorescent probes that provide spatiotemporally controllable imaging capabilities. However, conventional photoactive probes are limited by short auxiliary light wavelengths, prolonged irradiation times, and lack of analytes, making it difficult to achieve time-controlled imaging applications. Herein, a tetrazine-based probe (-) was synthesized for the light-assisted activation study.
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