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Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives

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Jérôme Waser, Eliott Hugo Joran Le Du, Emma Gabrielle Louise Robert
2022
journal articles

Abstract

An oxidative-decarboxylative intramolecular cyclisation of dipeptide derivatives is reported. This transformation is promoted by phenyl iodine(iii) diacetate (PIDA) in combination with BF3 center dot OEt2. The reaction gives access to a variety of valuable polycyclic N-heterocyclic scaffolds containing 5-, 6-, or 7-membered rings.

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https://infoscience.epfl.ch/entities/publication/cf05607e-6ff3-48d6-9510-27a86bf9422e

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Related concepts (5)

Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula . It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, . Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls.

Heterocyclic compound

A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles.

A ring system is a disc or ring, orbiting an astronomical object, that is composed of solid material such as dust and moonlets, and is a common component of satellite systems around giant planets like Saturn. A ring system around a planet is also known as a planetary ring system. The most prominent and most famous planetary rings in the Solar System are those around Saturn, but the other three giant planets (Jupiter, Uranus, and Neptune) also have ring systems.

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