An imidazolidin-1-ol, nitrone and oxadiazinane ring-chain-ring tautomeric dynamic combinatorial library

Coşkun, Necdet; Aksoy, Çağdaş

doi:10.1016/j.tetlet.2009.03.201

Cited by 8 publications

(1 citation statement)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recent studies have shown that ring−chain−ring tautomerism is a key pathway for the synthesis of various important compounds. The ring−chain−ring interconversion, 50,51 with the chain form being less stable than the ring form, may explain enantiomeric interconversion of the same cyclic derivative in which a chiral center is formed after the interaction of a single nucleophile−electrophile pair, a process that has been observed in the conversion of systems such as oxazolidine derivates. 19 In the current iteration of our approach, all ring−chain tautomers are simply enumerated by the application of a set of transformations.…”

Section: ■ Resultsmentioning

confidence: 99%

Enumeration of Ring–Chain Tautomers Based on SMIRKS Rules

Guasch

Sitzmann

Nicklaus

2014

J. Chem. Inf. Model.

View full text Add to dashboard Cite

A compound exhibits (prototropic) tautomerism if it can be represented by two or more structures that are related by a formal intramolecular movement of a hydrogen atom from one heavy atom position to another. When the movement of the proton is accompanied by the opening or closing of a ring it is called ring–chain tautomerism. This type of tautomerism is well observed in carbohydrates, but it also occurs in other molecules such as warfarin. In this work, we present an approach that allows for the generation of all ring–chain tautomers of a given chemical structure. Based on Baldwin’s Rules estimating the likelihood of ring closure reactions to occur, we have defined a set of transform rules covering the majority of ring–chain tautomerism cases. The rules automatically detect substructures in a given compound that can undergo a ring–chain tautomeric transformation. Each transformation is encoded in SMIRKS line notation. All work was implemented in the chemoinformatics toolkit CACTVS. We report on the application of our ring–chain tautomerism rules to a large database of commercially available screening samples in order to identify ring–chain tautomers.

show abstract

Section: ■ Resultsmentioning

confidence: 99%