934962-89-7Relevant academic research and scientific papers
Intramolecular Aza-Piancatelli Rearrangement of Alkyl- or Arylamines Promoted by PPh3/Diethyl Azodicarboxylate
Xu, Zhong-Li,Xing, Ping,Jiang, Biao
, p. 1028 - 1031 (2017/03/15)
A novel method for the construction of 1-azaspirocycles from 5-alkyl-/-arylamine furylcarbinols though intramolecular aza-Piancatelli rearrangement was developed. By using PPh3/diethyl azodicarboxylate instead of a Lewis acid, 1-azaspirocyclic compounds were obtained in good yields and the reaction temperature was reduced to room temperature. In addition, substrates with groups that are sensitive to high temperatures or Lewis acids are tolerated under these reaction conditions. This is the first method that is applicable not only to 5-(N-arylaminoalkyl)furylcarbinols with better yields but also to 5-(N-alkylaminoalkyl)furylcarbinols.
Highly efficient formal synthesis of cephalotaxine, using the stevens rearrangement-acid lactonization sequence as a key transformation
Sun, Mo-Ran,Lu, Hong-Tao,Wang, Yan-Zhi,Yang, Hua,Liu, Hong-Min
experimental part, p. 2213 - 2216 (2009/08/07)
Cephalotaxine (1), the major alkaloid isolated from Cephalotaxus species, has attracted considerable attention due to the promising antitumor activity of several of its derivatives and its unique structural features. Herein we describe a highly efficient formal synthesis of 1 employing the [2,3]-Stevens rearrangement-acid lactonization sequence as a key transformation from readily available (3,4-dimethoxyphenyl)acetic acid, methyl prolinate, and allyl bromide.
Novel formal synthesis of cephalotaxine via a facile friedel - Crafts cyclization
Li, Wei-Dong Z.,Wang, Xin-Wei
, p. 1211 - 1214 (2008/01/05)
Figure presented A novel formal synthesis of cephalotaxine (CET), the parent structure of the antileukemia Cephalotaxus alkaloids, was achieved via a facile Friedel-Crafts cyclization of the amino (or amido) spiro-cyclopentenone precursor (A) mediated by
