2113-88-4Relevant articles and documents
3-hydrazido and 3-hydrazono derivatives of tenuazonic acid and their herbicide evaluation
Liu, Yu-Xiu,Cui, Zhi-Peng,Li, Yong-Hong,Gu, Yu-Cheng,Wang, Qing-Min
, p. E197-E201 (2014)
With the aim of optimizing the structure of tenuazonic acid and improving the herbicidal activity, hydrazine moieties were introduced to the 3-position of pyrrolidine-2,4-dione scaffold of tenuazonic acid. 3-Hydrazido-pyrrolidine-2,4- dione compounds (4a, 4b, 4c, 4d, 4e) were prepared from corresponding carboxylates and hydrazines via a microwave-assisted amidation, whereas 3-hydrazono compounds (7a, 7b, 7c, 7d, 7e) were prepared from corresponding 3-acetyl pyrrolidine-2,4-dione. Both of the two structures also exhibited herbicidal activities, especially against the dicotyledonous species amaranth pigweed (Amaranthus retroflexus), but with different structure-activity relationship.
Tetramic Acid Chemistry. Part 1. Reinvestigation of Racemisation during the Synthesis of Tetramic Acids via Dieckmann Cyclisation
Poncet, Joel,Jouin, Patrick,Castro, Bertrand,Nicolas, Louisette,Boutar, Mohamed,Gaudemer, Alain
, p. 611 - 616 (2007/10/02)
Epimerisation during the synthesis of tetramic acids by Dieckmann cyclisation of the corresponding chiral N-acyl-α-amino esters was investigated.In the case of the isoleucine derivative, the extent of epimerisation was directly evaluated by 1H NMR analysis of the 3-acylated tetramic acids (3a,b) and (5a).A chemical correlation was carried out in the case of the 5-benzyl derivative (8h).The moderate overall yield and the partial epimerisation at position C-5 limit the usefulness of this approach for tetramic acid preparation.