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One‐Pot and Two‐Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D‐Labeled Derivativesстатья Исследовательская статья
- Авторы: Ledovskaya Maria, Polynski Mikhail, Ananikov Valentine P.
- Журнал: Chemistry - An Asian Journal
- Год издания: 2021
- Издательство: Wiley - V C H Verlag GmbbH & Co.
- Местоположение издательства: Germany
- DOI: 10.1002/asia.202100562
- Аннотация: Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2-H2O mixture performed in a two-chamber reactor led to corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95-99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.
- Добавил в систему: Анаников Валентин Павлович