Amidation and Intramolecular Aza‐Michael Reaction: One‐Pot Synthetic Strategy of Isoindolinones

Abstract

Herein, we report one-pot Cu(I) catalyzed open flask synthetic strategy of 3-substituted N-pyridinyl isoindolinones from alkyl (E)-3-(2-formylphenyl)acrylate by oxidative amidation and intramolecular aza-Michael reaction using cheap air stable Cu(I) single catalyst. We have also established a synthetic route of Naryl substituted isoindolinones with acid-amine coupling reaction of (E)-2-(3-alkoxy-3-oxoprop-1-en-1-yl)benzoic acid followed by aza-Michael reactions. Unexpected synthetic route of N-(1H-inden-1-yl)pyridin-2-amine derivatives have been documented from the same precursors using Cu(I) catalyst.

Energetic Nitrate-Based Polymer-Bonded Explosives Derived from Sustainable Aza-Michael Reactions

“…The lower activation energy observed by the Kissinger method than the theoretically predicted value is due to the catalytic action of Cu 2 I 2 and also the simultaneous cross-linking reaction of TMPTA with TETA. The catalysis of aza-Michael reactions using cuprous halide was reported by Kantam et al and Kang et al separately. , The promising catalytic activity of CuI for aza-Micahel addition was reported by Asraf Ali et al, and a plausible mechanism was also suggested. , …”

“…32,33 The promising catalytic activity of CuI for aza-Micahel addition was reported by Asraf Ali et al, and a plausible mechanism was also suggested. 34,35 2.2.4. Morphology Studies.…”

The isolation-biological activities (2014–2022), bio, semi, total synthesis (1978–2022) and SAR studies of a potential naturally engineered scaffold aristolactam

“…5. [22][23][24][25][26] Additionally, in medicinal chemistry aspects to involve a scaffold in the development of drugs, the scope of expansion of huge chemical space is also important. The interesting huge chemical space of aristolactams can be facilitated by new derivative chemical space expansion (NDCSE) (Fig.…”

Carbene-Catalyzed Tandem Imine Umpolung–Intramolecular Aza-Conjugate Addition–Oxidation to Access N-Substituted Isoindolinones

“…Hence, the construction of these potentially valuable scaffolds has received considerable attention resulting in the development of several synthetic strategies . Although, numerous synthetic methods were reported, most of those efforts rely on harsh reaction conditions, toxic, expensive transition metal complexes/ligands, the prerequisite installation of directing groups, the amide starting material, the use of stoichiometric amounts of additives/oxidants, and a limited substrate scope (Scheme a). , To the best of our knowledge, there are very few reports available for the synthesis of isoindolinone acetate motifs using organocatalysis. Michon and co-workers reported a phase transfer-catalyzed intramolecular aza-Michael addition for the synthesis of isoindolinone acetates using ortho -alkenyl substituted benzamides (Scheme b) .…”