62214-73-7Relevant academic research and scientific papers
FLAVONOIDS, XXXVII. RING CONTRACTION AND RING ENLARGEMENT REACTIONS WITH TRIMETHYLSILYL AZIDE IN THE FIELD OF FLAVONOIDS
Litkei, Gy.,Patonay, T.
, p. 47 - 56 (2007/10/02)
The reaction of flavanone with trimethylsilyl azide (TMSA) in trifluoroacetic acid (TFA) afforded by ring expansion, 2,3-dihydro-2-phenyl-1,4-benzoxazepin-5(4H)-one or 2,3-dihydro-2-phenyl-4H-tetrazolo-1,4-benzoxazepine.The same products could be isolated using sodium azide in TFA.An unknown intermediate of the Schmidt reaction was also isolated.Treatment of 2'-hydroxychalcone with TMSA or sodium azide in TFA resulted in isoflavone and trans-3-aminoflavanone.The reaction of 4-substituted 2'-hydroxychalcones with TMSA in dimethylformamide gave, with ring contraction, aurones and flavones.
