Synthesis of New Pyrrolo Heterocycles (I): Novel Synthesis of Pyrano[2,3‐c]pyrrole, Isoindoline, Pyrrolo[3,4‐b]pyridine, and Pyrrolo[3,4‐d]pyrimidine Derivatives

Abstract

Michael addition of 1,5‐diaryl‐2,3‐dioxopyrrolidine derivatives with α‐cyanocinnamonitriles and ethyl α‐cyanocinnamates afforded 4H‐pyrano[2,3‐c]pyrrole derivatives in the presence of sodium ethoxide. Under the same reaction condition, the ylidenes of 1,5‐diaryl‐2,3‐dioxopyrrolidine were reacted with malononitrile or ethyl cyanoacetate to give isoindole derivatives; however, pyrrolo[3,4‐b]pyridine derivatives were formed when cyanoacetamide was used. Moreover, pyrrolo[3,4‐d]pyrimidine derivatives were synthesized by treating 4‐benzylidene‐1,5‐diphenyl‐2,3‐dioxopyrrolidine with urea and/or thiourea under basic conditions. The structures of all the new synthesized compounds were confirmed by elemental analysis, IR and NMR spectra.

Recent Advances in the Synthesis of 3,4-Dihydropyran-2-Ones Organocatalyzed by N-Heterocyclic Carbenes

“…Similar research w by Shen and co-workers, who achieved a yield of 82% and an excellent %e on a gram scale [57]. Molecules such as 24 and derivatives are highly imp thetic chemistry as they provide fast and simple access to the synthesis of great therapeutic potential [58].…”

Pyrrolidine‐2,3‐diones: Synthesis, reactions and biological activity

“…Pyrrolidinediones (Figure 1) and related compounds play an important role in organic synthesis, as well as in modern therapeutics due to their wide range of biological and pharmacological activities. In particular, pyrrolidine‐2,3‐diones are the starting materials for the synthesis of a variety of structures containing the pyrrolidine ring such as the alkaloid vasicine 1–3 and pyrrolo‐fused heterocycles 4 . There is also increasing interest in pyrrolidine‐2,3‐diones as precursors to azetidin‐2‐ones and their use as antibiotic intermediates 5–7 …”