Asymmetric synthesis of 4,1-benzoxazepine-2,5-diones--effect of the halogen of (2S)-α-haloacids

Syeda Laila Rubab; Bushra Nisar; Abdul Rauf Raza; Nisar Ullah; Muhammad Nawaz Tahir

doi:10.3390/molecules19010139

Asymmetric synthesis of 4,1-benzoxazepine-2,5-diones--effect of the halogen of (2S)-α-haloacids

Molecules. 2013 Dec 23;19(1):139-48. doi: 10.3390/molecules19010139.

Authors

Syeda Laila Rubab, Bushra Nisar, Abdul Rauf Raza¹, Nisar Ullah², Muhammad Nawaz Tahir

Affiliations

¹ Ibn-e-Sina Block, Department of Chemistry, University of Sargodha, Sargodha 40100, Pakistan. roofichemist2012@gmail.com.
² Ibn-e-Sina Block, Department of Chemistry, University of Sargodha, Sargodha 40100, Pakistan. nullah@kfupm.edu.sa.

Abstract

Novel chiral 4,1-benzoxazepine-2,5-diones have been unusually synthesized in a single step by exploiting the chiral pool methodology. Substituted anthranilic acids afford N-acylanthranilic acids and (3R)-3-alkyl-4,1-benzoxazepines-2,5-dione upon coupling with α-chloroacids or α-bromoacids, respectively.

Publication types

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

MeSH terms

Combinatorial Chemistry Techniques
Cyclization
Halogens / chemistry*
Molecular Conformation
Oxazepines / chemical synthesis
Oxazepines / chemistry*

Substances

4,1-benzoxazepine
Halogens
Oxazepines