Developments in Transformations of (N-Isocyanoimino)Triphenylphosphorane: A Review Publisher



Doraghi F ; Kalooei Y M ; Navid H ; Larijani B ; Mahdavi M
Source: Monatshefte fur Chemie Published:2026

Abstract

Compared to other isocyanides, (N-isocyanoimino)triphenylphosphorane (NIITP) is an air-stable, moisture-stable, safe, easy-to-handle, odorless, and commercialized solid that is recognized as an appealing reagent for the synthesis of heterocyclic compounds. NIITP-based multi-component reactions have attracted considerable attention from chemists due to their synthetic potential, one-step, atom efficiency, and creation of molecular diversity. Many bioactive heterocyclic molecules, such as oxadiazoles, triazoles, pyrazoles, and pyrrolidine-2,5-diones can be efficiently synthesized from NIITP. Multi-component reactions of NIITP are typically carried out with carboxylic acids, aldehyde/ketone and amine segments. In new multi-component reactions, aldehyde or imine electrophiles are replaced by carbodiimides, activated isocyanates or acetylene dicarboxylates, and Meldrum’s acid, β-diketones and 4(3H)-quinazolinones are used instead of carboxylic acid, leading to the synthesis of new heterocyclic compounds. NIITP also participates in various functionalization reactions, providing a series of functionalized molecules. Given the unique and versatile functionality of this precursor, in this review, we have described transformations of NIITP into functionalized heterocycles, since 2000. © Springer-Verlag GmbH Austria, part of Springer Nature 2026.