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.
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.
Brouillette
Yann
Y
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.
Lisowski
Vincent
V
Fulcrand
Pierre
P
Martinez
Jean
J
D000577:Amides / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry
C519476:1H-thieno(3,2-d)(1,3)oxazine-2,4-dione; C519477:3,4-dihydro-1H-thieno(3,2-e)(1,4)diazepine-2,5-dione; D000577:Amides; D000812:Anhydrides; D001381:Azepines; D010078:Oxazines