Reactivity of β-(trifluoromethyl) acroleins towards primary alkyl (or aryl) amines: synthesis of (trifluoromethyl)-1-aza-1,3-dienes and secondary (trifluoromethyl) allylamines

Synthesis and Characterization of New Variously Substituted Allylic Phosphates

“…These were carefully measured from our own samples that were consistent with literature values [27][28][29] and compared with those obtained for phosphates 3 ( Table 2).…”

“…The integration of these signals gave approximately the same isomer percentages as those observed in the starting aldehydes 1 [27][28][29] and alcohols 2 [30].…”

“…The phosphorochloridates [33,34], aldehydes (1) [27][28][29], and alcohols (2) [30] were prepared following literature methods.…”

“…Our strategy to prepare the new allylic phosphates (Scheme 1) is based on the use of the starting β−chloro-α,β-unsaturated aldehydes 1, prepared by the Vilsmeier-Haack reaction [27][28][29], which were reduced using NaBH 4 in THF as previously described [30] to give the corresponding allylic alcohols 2. These were reacted with a phosphorochloridate to yield allylic phosphates 3.…”

One pot synthesis of novel α,β-dichloro-β-trifluoromethylated enones and their application to the synthesis of trifluoromethylated heterocycles

“…Among such building blocks, we are interested in the preparation of b-chlorinated b-trifluoromethyl enones which are very useful building blocks to provide trifluoromethyl substituted heterocycles, such as pyrazoles, isoxazoles and pyrimidines [4][5][6][7]. Although several methods for the preparation of b-chloro-b-trifluoromethylated enones and their application to the synthesis of heterocycles have been well documented in the previous literatures [6,8,9], however, there has been no report on the preparation of a,b-dichloro-btrifluoromethylated enones. Advantage of this a,b-dichloro enones as compared to b-chloro enones in the synthetic point of view is to be able to utilize the chloro functionality on the ring after synthesis of heterocyclic compounds and thus extend the functionality of heterocyclic ring system.…”