14593-04-5Relevant articles and documents
Reaction of 1,3-dioxanes with acetone cyanohydrin
Kuznetsov,Brusilovskii
, p. 574 - 575 (2001)
The reaction of 4-phenyl- and 4,4-dimethyl-1,3-dioxanes with acetone cyanohydrin leads to hydrolytically unstable 2-(1-hydroxy-1-methylethyl)-5,6-dihydro-1,3-oxazines, which are readily saponified in alkaline medium to the corresponding 1,3-amino alcohols
Base-induced Sommelet–Hauser rearrangement of N-(α-(2-oxyethyl)branched)benzylic glycine ester-derived ammonium salts via a chelated intermediate
Baba, Souya,Hirano, Kazuki,Tayama, Eiji
supporting information, (2020/03/13)
The base-induced Sommelet–Hauser (S–H) rearrangement of N-(α-branched)benzylic glycine ester-derived ammonium salts 1 was investigated. When the α-branched substituent was a simple alkyl, such as a methyl or butyl, desired S–H rearrangement product 2 was obtained in low yield with formation of the [1,2] Stevens rearranged 4 and Hofmann eliminated products 5 and 6. However, when the α-branched substituent had a 2-oxy moiety, such as 2-acetoxyethyl or 2-benzoyloxyethyl, the yields of 2 were improved. These results could be explained by formation of chelated intermediate C that stabilizes the carbanionic ylide, and the subsequent initial dearomative [2,3] sigmatropic rearrangement would be accelerated. The existence of C was supported by mechanistic experiments. This enhancement effect is not very strong or effective; however, it will expand the synthetic usefulness of ammonium ylide rearrangements.
Method for preparing amino alcohol compound by using halogenated intermediate
-
, (2020/08/22)
The invention discloses a method for preparing an amino alcohol compound by utilizing a halogenated intermediate. According to the method, an oxygen-halogen bond can be prepared by utilizing cyclic diacyl peroxide and halogenated salt under an illumination condition, and the oxygen-halogen bond is prone to homolysis under an illumination condition to form an active free radical, so the amino alcohol is finally prepared. The novel method for synthesizing the amino alcohol is high in atom utilization rate, simple in synthesis method and high in yield, so the consumption of halide for reactions with synthesis values is reduced, and the purposes of environmental protection and green chemistry are better achieved.
Lipophilic NHC assisted one-pot synthesis of syncarpamide analogues in aqueous medium
Suresh, Pavithira,Selva Ganesan, Subramaniapillai
supporting information, p. 6257 - 6261 (2019/04/25)
Lipophilic NHC catalysis in aqueous medium was reported for the synthesis of biologically relevant (a)symmetrically substituted and unsymmetrically substituted syncarpamide analogues. All the reported reactions were performed in the absence of any expensive metal salts or additives. A diverse array of syncarpamide analogues was obtained in good yields. Lipophilic NHC catalysis was also extended to chemoselective transesterification reactions.
