Nitrile N-Oxides and Nitrile Imines as New Fuels for the Discovery of Novel Isocyanide-Based Multicomponent Reactions

Abstract

With this short review we would like to describe our work on isocyanide-mediated multicomponent reactions using the 1,3-dipolar species nitrile N-oxides and nitrile imines as electrophilic inputs. Our goal is to show the potentiality of these transformations, elucidate the mechanisms of the reactions, demonstrate the versatility, and highlight the potentiality of this chemistry.\ud 1 Introduction\ud 2 (Z)-ChloroximesasElectrophilicPartnersforIsocyanides\ud 2.1 Precedents for the Reaction Between Nitrile N-Oxides and Iso-\ud cyanides\ud 2.2 Reaction between (Z)-Chloroximes, Isocyanides, and Carboxylic\ud Acids (or Amines)\ud 2.3 The Use of Other Nucleophiles as the Third Partner\ud 2.4 General Mechanism\ud 3 Nitrile Imines as Electrophilic Partners for Isocyanides\ud 4 Conclusions and Future Outloo

α-Amino Acids as Synthons in the Ugi-5-Centers-4-Components Reaction: Chemistry and Applications

“…In particular, Isocyanide-based Multicomponent Reactions (IMCRs) [1][2][3][4], have been proven to be an ideal tool to provide in one single step medium-complexity molecular skeletons, usually accessible only via a multistep approach. Most of MCR chemistry is performed with isocyanides and is related to the Ugi reaction [5,6], a four-component transformation (4CR) described in 1959 by Professor Ivar Ugi. In the reaction, an acid component, like a carboxylic acid, reacts with an oxo-component (a ketone or an aldehyde), a primary amine, and an isocyanide.…”

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

“…Many noval MCRs [57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73] have meanwhile become part of the range of syntheses, e.g. boron-mediated [62,66], photo-induced [67] and carbenebased MCRs [72] such as N-heterocyclic carbenes (NHCs).…”

“…Scifinder) about the target products and intermediates of the synthesis plan. With respect to 1: New and in particular novel MCRs [38,45,61,82,83,114,115,[176][177][178][179][180][181][182] are the basis and guarantee for high diversity and therewith the capacity to produce many structurally-different compounds. A method has been found to design MCRs going from libraries of compounds to libraries of reactions [180].…”

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

“…IMCRs [ 38 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ], alkyne-based [ 38 , 51 , 52 , 53 , 54 ] and C-H-acidic compound [ 55 , 56 , 57 , 58 , 59 , 60 ]-based MCRs in particular have a high potential to be very diverse. Many novel MCRs [ 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 ] have meanwhile become part of the range of syntheses, e.g., boron-mediated [ 62 , 66 ], photo-induced [ 67 ] and carbene-based MCRs [ 72 ] such as N-heterocyclic carbenes (NHCs). They all increase the application options for MCRs, such as MCR nanosystems and mechanochemical reactions [ 65 ].…”

“…With respect to 1: New and in particular novel MCRs [ 38 , 45 , 61 , 81 , 82 , 112 , 113 , 154 , 157 , 174 , 175 , 176 , 177 , 178 ] are the basis and guarantee for high diversity and therewith the capacity to produce many structurally-different compounds. A method has been found to design MCRs going from libraries of compounds to libraries of reactions [ 176 ].…”