Novel synthesis of a conformationally-constrained analog of DDATHF

Synthesis of functionalized isoindolinones: Addition of in situ generated organoalanes to acyliminium ions

“…1). Isoindolinones demonstrate a remarkably wide array of biological activities, including anti-inflammatory [4], antihypertensive [5], antipsychotic [6], vasodilatory [7] and antileukemic [8] effects, which renders the development of new synthetic routes toward these heterocycles particularly attractive. While several methods have been reported for the preparation of isoindolinones [9], some leading to the synthesis of natural products [10] and compound libraries [11], many approaches suffer from a lack of generality or functional group compatibility.…”

Facile ligand-free Pd-catalyzed tandem C–C/C–N coupling reaction: a novel access to highly diverse tetrazole tag isoindoline derivatives

“…4 These heterocyclic frameworks have attracted considerable attention in synthetic organic and medicinal chemistry due to their broad structural diversity and broad-spectrum biological activities, including: Endothelin-A Receptor Antagonists, 5 inhibition of prolyl dipeptidase DPP8, 6 PPARᵹ agonists, 7 histone deacetylase inhibitors, 8 inhibitors of selective serotonin reuptake, 9 diuretic, NMDA receptor antagonists, herbicidal, 10 anti-inflammatory and antileukemic agents. 11 Furthermore, isoindolines inhibit the amyloid protein aggregation which demonstrate a potency in the treatment of Alzheimer's disease, the ligand affinity for the melanocortin subtype-4 receptor (MC4R) (D), act as multidrug resistance reversal agents, and fibrinogen receptor antagonists. 12,13 On the other side, tetrazole is an extremely valuable scaffolds due to their diverse biological activity.…”

Quaternary Ammonium Salt‐Promoted Multi‐Component Reaction in Water: Access to 3‐Alkyl‐2, 3‐Dihydro‐1H‐Isoindolin‐1‐One Derivatives

“…[1] Among the various N-heterocylic compounds, functional isoindolinone frameworks are a privileged class of building blocks since they show a wide range of biological activities and therapeutic potential, [2] such as antihypertensive, [3] antipsychotic, [4] anesthetic, [5] antiulcer, [6] vasodilatory, [7] antiviral, [8] and antileukemic [9] properties. In particular, 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones are omnipresent as key structural scaffolds in many medicinal molecules, in which pagoclone (1 a), [10] pazinaclone (DN 2327, 1 b), [11] (R)-JM 1232 (1 c), [12] (S)-PD 172938 (1 d), [13] and (1 e) [14] are in the most representative ( Figure 1).…”