Abstract
Ninhydrin has been utilized in many heterocyclic pr eparations and considered as an important building block in organic synthesis. There is a wid e range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review hi ghlights the advances in the use of ninhydrin as starting material in the synthesis of various organ ic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.
Highlights
Ninhydrin was first made in 1910 by an English chemist Siegfried Ruhemann, who investigated its reaction with amines and amino acids to form a colored compound.[1,2] The product of this reaction is a compound known as Ruhemann’s purple (Rp),[3,4] which has a maximum absorption at 570 nm
This review has summarized the use of ninhydrin in the synthesis of heterocyclic compounds with respect to the number of atoms in heterocyclic rings, taking into consideration the heteroatom
We have demonstrated that ninhydrin is a very versatile substrate, as it can be used for the synthesis of a large variety of heterocyclic compounds
Summary
Ninhydrin was first made in 1910 by an English chemist Siegfried Ruhemann, who investigated its reaction with amines and amino acids to form a colored compound.[1,2] The product of this reaction is a compound known as Ruhemann’s purple (Rp),[3,4] which has a maximum absorption at 570 nm. Ninhydrin is a stable hydrated product of indane-1,2,3-trione, which is considered to be a very important analytical tool in organic, peptide, biochemical, analytical and forensic sciences (Figure 1).[5,6,7,8,9,10]. Considering the importance of ninhydrin as a building block in organic synthesis, and as there are a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds, we have summarized the most prominent reactions in which one of the starting materials was ninhydrin. First we introduce different synthetic routes to prepare ninhydrin, and second, we review the use of ninhydrin as a starting material in the synthesis of different heterocyclic compounds, the order being based on the type of heterocycles formed. Biological, or pharmacological data and uses of ninhydrin will be mentioned when available
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