Stefano Marcaccini: a pioneer in isocyanide chemistry

Abstract

Stefano Marcaccini was one of the pioneers in the use of isocyanide-based multicomponent reactions in organic synthesis. Throughout his career at the University of Florence he explored many different faces of isocyanide chemistry, especially those geared towards the synthesis of biologically relevant heterocycles. His work inspired many researchers who contributed to other important developments in the field of multicomponent reactions and created a school of synthetic chemists that continues today. In this manuscript we intend to review the articles on isocyanide multicomponent reactions published by Dr. Marcaccini and analyse their influence on the following works by other researchers. With this, we hope to highlight the immense contribution of Stefano Marcaccini to the development of isocyanide chemistry and modern organic synthesis as well as the influence of his research on future generations. We believe that this review will not only be a well-deserved tribute to the figure of Stefano Marcaccini, but will also serve as a useful inspiration for chemists working in this field. Graphical abstract

Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles

“…Different strategies have been developed to avoid these competitive reactions, the most common ones being the use of protecting groups (Ugi/deprotection/cyclization strategy) [ 12 – 14 ] or of surrogates of amines [ 15 ]. However, direct incorporation of the second amine without derivatization is the most desirable strategy from the point-of view of sustainability.…”

Synthesis of Tetrahydronaphthoazetidinones, 2,5‐Dioxo‐1,4‐methanobenzoazepines and 3‐Hydroxypyrrolidinones Through Copper‐Assisted Post‐Ugi Reactions

“…The Ugi fourcomponent reaction is an isocyanide-based multicomponent reaction of prominent relevance. [2] Coupled to post-Ugi modifications, this type of reactions have proved as a valuable synthetic strategy to access a large number of complex functionalized heterocyles. [3] In particular, different methodologies for the synthesis of heterocyclic systems employing the Ugi reaction followed by radical cyclizations have been described in the last few years.…”