One-pot, large-scale synthesis of Nickel(II) complexes derived from 2-[N-(alpha-picolyl)amino]benzophenone (PABP) and alpha- or beta-amino acids

Guanghui Deng; Jiang Wang; Yu Zhou; Hualiang Jiang; Hong Liu

doi:10.1021/jo071011e

One-pot, large-scale synthesis of Nickel(II) complexes derived from 2-[N-(alpha-picolyl)amino]benzophenone (PABP) and alpha- or beta-amino acids

J Org Chem. 2007 Nov 9;72(23):8932-4. doi: 10.1021/jo071011e. Epub 2007 Oct 19.

Authors

Guanghui Deng¹, Jiang Wang, Yu Zhou, Hualiang Jiang, Hong Liu

Affiliation

¹ Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Graduate School of the Chinese Academy of Sciences, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, China.

PMID: 17949038
DOI: 10.1021/jo071011e

Abstract

A one-pot, large-scale procedure for preparing the Belokon-Soloshonok nucleophilic glycine equivalent 2-[N-(alpha-picolyl)amino]benzophenone (PABP) derived Ni(II) complex [GlyNi(II)PABP] is described. It has been accomplished by using isobutyl chloroformate to form PABP and then NaH/KOH as mixed bases to afford the corresponding complexes in a one-pot manner (up to an overall yield of 98%). The potential of this method for preparation of beta-amino acids derivatives, such as beta-AlaNi(II)PABP and beta-PheNi(II)PABP, has been demonstrated. The structure of beta-AlaNi(II)PABP is characterized by single-crystal X-ray diffraction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Benzophenones / chemistry*
Combinatorial Chemistry Techniques
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Nickel / chemistry*
Organometallic Compounds / chemical synthesis*
Organometallic Compounds / chemistry
Stereoisomerism

Substances

2-(N-(alpha-picolyl)amino)benzophenone
Amino Acids
Benzophenones
Organometallic Compounds
Nickel