A new class of bifunctional organocatalysts containing both thiazolidine/pyrrolidine and imidazole cycles was prepared via a readily available synthetic route.
Herein, we describe the development of a short, simple, and efficient synthesis of amino‐ and hydroxymethyl‐substituted benzoxaboroles. The key step in our strategy was the early stage incorporation of the boron by the borylation of an aniline. The formed boronates were then elaborated to the final products in two additional steps, usually in good yields. The synthetic sequence was amenable to be performed on a preparative scale and 4‐amino benzoxaborole 4b and 6‐hydroxymethyl benzoxaborole 10c have been prepared, without any significant decrease in the overall yield. The amino and hydroxymethyl present at the molecules are useful for further elaboration and/or conjugation to bioactive molecules and therefore we believe that this method should be useful in the development of new compounds for Medicinal Chemistry.
Herein, we describe the C4‐ethoxylation of 2,4‐dichloroquinoline to prepare 2‐chloro‐4‐ethoxy‐quinoline (3), which is a prominent intermediate used for the synthesis of 2‐substituted quinolones. To achieve this goal, we studied different conditions for the reaction between 2,4‐dichloroquinoline and sodium ethoxide. We discovered that the use of 18‐crown‐6 ether as an additive and dimethylformamide as the reaction solvent allowed us to obtain the desired product 3 in very good yield and selectivity. In addition, a definitive distinction between the C2 and C4 ethoxylation products was achieved using 1H─15N heteronuclear multiple bond correlation. Compound 3 is an intermediate used for the synthesis of 2‐((3‐aminopropyl)amino)quinolin‐4(1H)‐one, which displays peculiar behavior during 1H nuclear magnetic resonance analysis, such as the broadening of the H8 singlet and unexpected deuteration at the C8‐position. Effort has been dedicated to understand these findings.
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