Synthesis of Polysubstituted Pyridine Derivatives via Sequential AlCl₃‐Catalyzed Condensation/Aza‐Wittig/Isomerization Reactions and a Study of their Antifungal Activities

Abstract

A facile approach to access polysubstituted pyridine derivatives starting from Baylis-Hillman adducts is disclosed. The reactions proceeded smoothly by sequential AlCl 3 -catalyzed condensation/aza-Wittig/isomerization reactions, leading to the target products at room temperature within 24 h in moderate to good yields. Furthermore, the final products were evaluated in mycelial growth tests against Pythium dissimile, Botryotinia fuckeliana and Zymoseptoria tritici and showed potential activities.

Hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through Pd-catalyzed isocyanide insertion reaction involving aziridines

“…14 b The above reports indicate that aziridines often undergo ring-opening/cycloaddition reactions under certain conditions, which also brings challenges for our proposed isocyanide insertion reactions involving aziridines as nucleophiles. Based on our previous research on isocyanide chemistry and heterocyclic synthesis, 16 our group has been exploring the feasibility of binding new nucleophiles to isocyanide molecules. In the context of our studies on isocyanide chemistry, we herein aim to present a hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through a Pd-catalyzed isocyanide insertion reaction involving aziridines (Scheme 1d).…”

Pd-catalyzed imine-directed one-pot access to polysubstituted pyrrolesviatandem triple isocyanide insertion/aza-Nazarov cyclization reactions

“…Nitrogen heterocyclic compounds are essential skeletons frequently found in pharmaceuticals, 1 natural products, 2 and functional materials. 3 Among them, the versatile pyrrole derivatives have been widely utilized as antimicrobials, 4 anti-tubercular agents, 5 enzyme inhibitors, 6 and anticancer agents 7 in the areas of biochemistry and life science.…”

Isocyano(triphenylphosphoranylidene)acetates: Key to the One-Pot Synthesis of Oxazolo[4,5-c]quinoline Derivatives via a Sequential Ugi/Wittig/aza-Wittig Cyclization Process

“…In our previous work, multifunctional isocyano­(tri­phenyl­phos­phoranyl­idene)­acetates were first proposed to participate in the Ugi-4CR while the ester group was abandoned. To further advance our work in this field, herein we disclose our recent efforts for synthesis of oxazolo­[4,5- c ]­quinoline derivatives starting from multifunctional isocyano­(tri­phenyl­phos­phoran­yl­idene) acetates by a sequential Ugi/Wittig/aza-Wittig reaction (Scheme d).…”