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

Abstract

A new one-pot preparation of dibenzo[b,e]azepin-6(11H)-one by a sequential Ugi-4CR and sulfur ylide-mediated rearrangement reaction has been developed. A series of polysubstituted dibenzo[b,e]azepin-6(11H)-ones were obtained in 69-84 % yields from readily available sulfonium salts, 2-aminophenyl ketones, aldehydes and isocyanides in the presence of DBU.

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.…”