Synthesis of β- and γ-lactam fused dihydropyrazinones from Ugi adducts via a sequential ring construction strategy

Abstract

A modular approach for the construction of β- and γ-lactam fused dihydropyrazinones from the readily available Ugi adducts has been described. The sequencial construction of rings through base-mediated cycloisomerization followed...

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

“…In this direction, our group demonstrated the regioselective construction of β‐ and γ‐lactam fused dihydropyrazinones 53 and 54 from alkynoic acid‐derived Ugi adducts 52 (Scheme 17). [26] The sequential construction of rings through base‐mediated cycloisomerization, followed by acid‐mediated cyclization, yielded β‐lactam fused dihydropyrazinones 53 in a 4‐ exo‐dig fashion. However, the Ugi‐derived dihydropyrazinones afforded γ‐lactam fused dihydropyrazinones 54 under base‐mediated cycloisomerization in a 5‐ endo‐dig manner.…”

“…Our research group is actively engaged in exploring novel post‐Ugi transformations [21–25] and recently, we have been working on base‐mediated post‐Ugi transformations to access novel bioactive compounds for drug discovery [26–29] . Encouraged by our findings and related research worldwide, we present an exciting review highlighting the base‐mediated post‐Ugi transformations by trapping the peptidyl anion.…”

Discovery of 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one derivatives as possible antileishmanial agents

“…2). 27 Inspired by previous reports and in continuation of our ongoing efforts to identify medicinally important structural frameworks, [28][29][30][31][32][33][34][35][36] a series of N-alkylated pyrroloquinolinone derivatives were designed and synthesized, and their antileishmanial efficacy was evaluated against visceral leishmaniasis (VL).…”

Facile synthesis and biological evaluation of tryptamine-piperazine-2,5-dione conjugates as anticancer agents

“…4 From similar Ugi adducts, the Srivastava group reported that this reaction could occur at room temperature in the presence of NaH. 5 The Van der Eycken group also published their ndings that a g-lactam core could be constructed under different conditions. 4b,6 Besides the C-C bond formation, the Zhang group reported a C-N bond formation protocol to build piperazine-2,5-dione core through alkyne and amide groups (Scheme 1).…”