97315-84-9Relevant academic research and scientific papers
Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides
Dolliver, Debra D.,Bhattarai, Bijay T.,Pandey, Arjun,Lanier, Megan L.,Bordelon, Amber S.,Adhikari, Sarju,Dinser, Jordan A.,Flowers, Patrick F.,Wills, Veronica S.,Schneider, Caroline L.,Shaughnessy, Kevin H.,Moore, Jane N.,Raders, Steven M.,Snowden, Timothy S.,McKim, Artie S.,Fronczek, Frank R.
, p. 3676 - 3687 (2013/06/04)
A high-yielding stereospecific route to the synthesis of single geometric isomers of diaryl oxime ethers through Suzuki coupling of N-alkoxyimidoyl iodides is described. This reaction occurs with complete retention of the imidoyl halide geometry to give single E- or Z-isomers of diaryl oxime ethers. The Sonogashira coupling of N-alkoxyimidoyl iodides and bromides with a wide variety of terminal alkynes to afford single geometric isomers of aryl alkynyl oxime ethers has also been developed. Several of these reactions proceed through copper-free conditions. The Negishi coupling of N-alkoxyimidoyl halides is introduced. The E and Z configurations of nine Suzuki-coupling products and two Sonogashira-coupling products were confirmed by X-ray crystallography.
Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone
Miyata, Okiko,Koizumi, Tomoko,Asai, Hiroshi,Iba, Ryuichi,Naito, Takeaki
, p. 3893 - 3914 (2007/10/03)
The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone.
Mechanism of Amine and Amide Ion Substitution Reactions at the Carbon-Nitrogen Double Bond.
Johnson, James Elver,Ghafouripour, Abdolkarim,Arfan, Mohammad,Todd, Susan L.,Sitz, Deborah A.
, p. 3348 - 3355 (2007/10/02)
Reactions of the (Z)-hydroximoyl chlorides 3a-e with secondary amines without solvent at 32 deg C for 24 h give high yields of (Z)-benzamidoximes 7a-f.Although the amidoximes 7a-f do not isomerize under the reaction conditions, they isomerize to the E iso
