One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions

Abstract

A new one-pot and divergent synthesis of multisubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/ Corey-Chaykovsky epoxidation reaction was developed. The four-component reactions of 2-acylanilines, aldehydes, (carboxymethyl)(dimethyl)sulfonium bromides...

Synthesis of Dibenzo[b,e]azepin‐6(11H)‐ones via a Sequential Ugi‐4CR and Sulfur Ylide‐Mediated Rearrangement Reaction

“…In our previous paper, a similar system undertakes however an elimination to give C=C double bond formation product quinolin-2(1H)-one. [10] But in present system, anti-elimination of water from intermediate (syn)-11 would produce eight-membered dibenzo[b,f]azocin-6(5H)-one 7, which has large ring tension and is relatively unstable.…”

“…[9] In our previous work, the sequential Ugi/Corey-Chaykovsky epoxidation and Ugi/Knoevenagel condensation/hydrolysis reaction were used to afford oxireno [2,3-c]quinolin-2(1aH,3H,7bH)-ones and quinolin-2(1H)-ones starting from (carboxymethyl)(dimethyl)sulfonium salt precursors. [10] So we envisioned that if the sulfonium salts 1 were utilized as starting material, the similar tandem cyclization would take place to produce epoxides 6 or dibenzo[b,f]azocin-6(5H)-one 7 (Scheme 1). By continuing our interest in the synthesis of various heterocycles via multicomponent reaction [11] , we wish to disclose herein an unexpected synthesis of dibenzo[b,e]azepin-6(11H)-one 8 instead of 6 or 7, by a domino Ugi-4CR/sulfur ylide-mediated rearrangement reaction starting from sulfonium salts 1 in a one-pot fashion.…”

Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction

“…Polysubstituted γ-lactams were prepared by sequential Ugi and radical cyclization-oxyamination process promoted by ammonium persulfate . In our previous work, we have also disclosed some efficient domino protocols for the synthesis of heterocyclic compounds by using post Ugi-3CR transformation. − Continuing our interest in the synthesis of N -heterocycles via multicomponent reactions, − we wish to report herein a new efficient synthesis of indolo­[2,1- b ]­quinazolin-6­(12 H )-ones via the sequential Ugi-3CR/iodine-promoted cyclization/Staudinger/aza-Wittig reaction. We also surveyed their luminescent properties in order to test their possible use as organic dyes or fluorescent probes.…”

Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction

“…1b). 10 Additionally, Maulide et al developed a stereodivergent olefination method based on unique thiouronium ylides. This selective transformation challenges the canonical reactivity of sulfur ylides toward carbonyl derivatives (Fig.…”