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Literature DB >> 20157342

A simple and expedient method for the preparation of N-chlorohydantoins.

Daniel C Whitehead¹, Richard J Staples, Babak Borhan.

Abstract

A simple and efficient methodology for the preparation of N-chlorinated hydantoins is presented. These versatile chlorenium sources were isolated in high yield after a simple recrystallization. Among the ten examples are the first chiral N-chlorohydantoins.

Entities: Chemical Disease Gene

Year: 2009 PMID： 20157342 PMCID： PMC2662602 DOI： 10.1016/j.tetlet.2008.11.091

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

11 in total

1. Asymmetric hydrogenation of heteroaromatic compounds.

Authors: Yong-Gui Zhou
Journal: Acc Chem Res Date: 2007-09-27 Impact factor: 22.384

2. Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones.

Authors: N S Barta; D R Sidler; K B Somerville; S A Weissman; R D Larsen; P J Reider
Journal: Org Lett Date: 2000-09-07 Impact factor: 6.005

3. 17-Heteroaroyl esters of corticosteroids. 2. 11 beta-Hydroxy series.

Authors: E L Shapiro; M J Gentles; R L Tiberi; T L Popper; J Berkenkopf; B Lutsky; A S Watnick
Journal: J Med Chem Date: 1987-09 Impact factor: 7.446

4. Metabolism of phenytoin and covalent binding of reactive intermediates in activated human neutrophils.

Authors: D C Mays; L J Pawluk; G Apseloff; W B Davis; Z W She; A L Sagone; N Gerber
Journal: Biochem Pharmacol Date: 1995-07-31 Impact factor: 5.858

5. Facile synthesis of 2-bromo-3-fluorobenzonitrile: an application and study of the halodeboronation of aryl boronic acids.

Authors: Ronald H Szumigala; Paul N Devine; Donald R Gauthier; R P Volante
Journal: J Org Chem Date: 2004-01-23 Impact factor: 4.354

6. Generation and cycloaddition of polymer-supported azomethine ylide via a 1,2-silatropic shift of alpha-silylimines: traceless synthesis of pyrrolidine derivatives.

Authors: Mitsuo Komatsu; Hirofumi Okada; Tatsuo Akaki; Yoji Oderaotoshi; Satoshi Minakata
Journal: Org Lett Date: 2002-10-03 Impact factor: 6.005

7. Comparative structural studies of iodide complexes of uranium(III) and lanthanide(III) with hexadentate tetrapodal neutral N-donor ligands.

Authors: Lydia Karmazin; Marinella Mazzanti; Jean-Philippe Bezombes; Christelle Gateau; Jacques Pécaut
Journal: Inorg Chem Date: 2004-08-09 Impact factor: 5.165

A simple and expedient method for the preparation of N-chlorohydantoins.

1. Asymmetric hydrogenation of heteroaromatic compounds.

2. Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones.

3. 17-Heteroaroyl esters of corticosteroids. 2. 11 beta-Hydroxy series.

4. Metabolism of phenytoin and covalent binding of reactive intermediates in activated human neutrophils.

5. Facile synthesis of 2-bromo-3-fluorobenzonitrile: an application and study of the halodeboronation of aryl boronic acids.

6. Generation and cycloaddition of polymer-supported azomethine ylide via a 1,2-silatropic shift of alpha-silylimines: traceless synthesis of pyrrolidine derivatives.

7. Comparative structural studies of iodide complexes of uranium(III) and lanthanide(III) with hexadentate tetrapodal neutral N-donor ligands.

8. N-chlorination of phenytoin by myeloperoxidase to a reactive metabolite.

9. Chemiluminescence flow injection analysis of 1,3-dichloro-5,5-dimethylhydantoin in swimming pool water.

10. Dichlorohydantoin and dibromohydantoin as new oxidimetric titrants in non-aqueous media.

1. An organocatalytic asymmetric chlorolactonization.