Reactivity study of 1H-thieno[3,2-d][1,3]oxazine-2,4-dione toward the synthesis of bicyclic 3,4-dihydro-1H-thieno[3,2-e][1,4]diazepine-2,5-dione analogues

Yann Brouillette; Vincent Lisowski; Pierre Fulcrand; Jean Martinez

doi:10.1021/jo0622882

Reactivity study of 1H-thieno[3,2-d][1,3]oxazine-2,4-dione toward the synthesis of bicyclic 3,4-dihydro-1H-thieno[3,2-e][1,4]diazepine-2,5-dione analogues

J Org Chem. 2007 Mar 30;72(7):2662-5. doi: 10.1021/jo0622882. Epub 2007 Feb 27.

Authors

Yann Brouillette¹, Vincent Lisowski, Pierre Fulcrand, Jean Martinez

Affiliation

¹ Laboratoire des Aminoacides, Peptides et Protéines (LAPP), CNRS UMR 5810, UMI-UMII, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5, France.

PMID: 17323999
DOI: 10.1021/jo0622882

Abstract

A series of 10 optically pure 3,4-dihydro-1H-thieno[3,2-e][1,4]diazepine-2,5-dione derivatives has been synthesized in 41-75% yields on treatment of 1H-thieno[3,2-d][1,3]oxazine-2,4-dione with different natural alpha-amino acids.

Publication types

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

MeSH terms

Amides / chemistry
Anhydrides / chemistry
Azepines / chemical synthesis*
Azepines / chemistry
Molecular Structure
Oxazines / chemical synthesis*
Oxazines / chemistry

Substances

1H-thieno(3,2-d)(1,3)oxazine-2,4-dione
3,4-dihydro-1H-thieno(3,2-e)(1,4)diazepine-2,5-dione
Amides
Anhydrides
Azepines
Oxazines