| Autor: |
Raymond, Justine L., Detta, Elena, Alza, Esther, Fianchini, Mauro, Pericàs, Miquel A. |
| Předmět: |
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| Zdroj: |
European Journal of Organic Chemistry; 1/15/2024, Vol. 27 Issue 3, p1-8, 8p |
| Abstrakt: |
Several strategies to synthesize desired 1,2,4‐triazolo[1,5‐a]pyridine‐2‐carboxylate targets have been reported over the years. The most convenient way features the preparation of the precursor triazolopyridine‐N‐oxide through a condensation step between sulfilimines and a nitrile oxide species, followed by a deoxygenation step. This paper presents a detailed work on the synthesis of [1,2,4]triazolo[1,5‐a]pyridine‐2‐carboxylate‐N‐oxide, featuring a synergistic experimental‐theoretical approach. Herein, we report the development of an efficient and straightforward method to prepare ethyl [1,2,4]triazolo[1,5‐a]pyridine‐2‐carboxylate 3‐oxide in continuous flow. The transfer from batch to flow processing resulted in a significant boost in isolated yield (53 % vs. 31 %) and a decrease in the simultaneous presence of starting materials and product in the reaction media from 4 hours to 3.5 minutes. An in‐depth mechanistic study of the reaction using density functional theory provided a deeper understanding of the whole reaction manifold and key indications on how to further improve the process in flow. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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