Mechanochemical IMCR and IMCR-post transformation domino strategies: towards the sustainable DOS of dipeptide-like and heterocyclic peptidomimetics

Abstract

The first, rapid, and inexpensive mechanochemical Ugi four-component reaction (MC-Ugi-4CR) has been developed for the sustainable synthesis of new dipeptides like products in high yields under mild, solvent-, catalyst-, and...

Isocyanide–Based Multicomponent Reactions Coupled One–Pot Process: Efficient Tools to Diversity–Oriented Synthesis of Structural Peptidomimetics

“…[11] Following our main research line focused on the design and development of efficient IMCR-based strategies to synthesize novel CCP, in one-pot, [35][36][37][38] or two steps [43][44][45] we Recently, we reported the one-pot DOS of CCP via IMCR/post-transformation strategy. [39] Herein, we increased the complexity of CCP including heterocyclic bioisosteres of the amide bond such as 1,2,3-triazoles and 1,5-DSÀ T.…”

“…According to our research line, we are interested in the development of novel strategies to access structural peptidomimetics coupling IMCRs with other efficient one-pot processes, [35][36][37][38] and their application in DOS. [39] Herein we describe a new DOS strategy to synthesize anchored analogues of 2,5-DKP fused to 1,2,3-triazole, with scaffold diversity incorporating a tetrazole ring in their structure (Scheme 2).…”

Ugi-4CR/SN2-Cyclization Strategy for the One-Pot Synthesis of 2,5-Diketopiperazines

“…These have several disadvantages, including the use of drastic reaction conditions that include high temperatures, strong bases and/or toxic reagents (for deprotection-based cyclization), and low global yields [4]. In this context, the isocyanide-based multicomponent reaction (IMCR) approach is advantageous in terms of facile reaction conditions, scope of the starting materials, broadness of synthetic variations, and synthetic efficacy, which contributes significantly to the development of environmentally friendly strategies [5][6][7][8].…”

“…efficacy, which contributes significantly to the development of environmentally friendly strategies [5][6][7][8].…”

Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions

“…The outstanding reactivity of the isocyanide functional group includes the ability to react with both electrophiles and nucleophiles simultaneously, and places isocyanide-containing compounds as privileged building blocks for synthetic, medicinal, and material chemistry applications. In particular, their compatibility with domino and cascade processes has paved the way for developing various isocyanide-based multicomponent strategies, which benefit from high degree of atom and bond economy and require relatively mild reaction conditions and simplicity of work up procedures [2][3][4][5].…”