Synthesis of N,O-acetals by net amide C N bond insertion of aldehydes into N-acyl phthalimides and N-acyl azoles

Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln; Paeth, Matthew; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.

doi:10.1016/j.tet.2016.08.041

Cited by 12 publications

(6 citation statements)

References 36 publications

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“…Unexpectedly, phenyl thiolate did not give any reaction. It was found that in the absence of a nucleophile and using a slight excess of the equimolar azole/DBU combination, hemiaminal esters 12 a – e were formed with high efficiency . By using cyanide as the nucleophile, the cyanohydrine ester 13 was obtained albeit in moderate but yet unoptimized yield.…”

Section: Methodsmentioning

confidence: 99%

Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

2018

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Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion.

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Section: Methodsmentioning

confidence: 99%

Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

2018

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“…In 2016, Willoughby and co-workers provided an approach to the synthesis of O -acyl- N , O -acetals 80 and 83 through amide C–N bond insertion (Scheme 33 ). 38 N -Acylphthalimides and several N -acylated azoles were demonstrated to react with various aldehydes under mild conditions. Additionally, in order to enhance operational simplicity, a one-pot procedure was developed, by which a wider range of products including those derived from N -acylphthalimides and other nitrogen-containing heterocycles were produced.…”

Section: Synthetic Methods For Preparing N -Acyl- N O -Acetalsmentioning

confidence: 99%

“…In 2016, Willoughby and co-workers provided an approach to the synthesis of O-acyl-N,O-acetals 80 and 83 through amide C-N bond insertion (Scheme 33). 38 N-Acylphthalimides and several N-acylated azoles were demonstrated to react with various aldehydes under mild condi-…”

Section: Short Review Synthesis Scheme 28 Phi(oac) 2 -Mediated Oxidat...mentioning

confidence: 99%

Progress in the Synthesis of N-Acyl-N,O-acetals

Shao

et al. 2021

Synthesis

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N-Acyl-N,O-acetals are key component a variety of bioactive natural products. Furthermore， they are synthetic equivalents of unstable N-acylimines and building blocks in organic synthesis. Tremendous efforts have been made to the synthesis of such acetals, these methods can roughly be classified into two categories: electrochemical oxidation and chemical methods. Herein, we want to summarize the progress made on the preparation of the subunits, which may provide assistance for the development of new synthetic methods of N-acyl-N,O-acetals.

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“…Compounds II-f−II-i were prepared according to the method reported previously. 35,36 Aroyl The mixture was filtered, and the solvent was removed under reduced pressure. The crude product was purified as compounds II-f−II-i.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Discovery of N-Aroyl Diketone/Triketone Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibiting-Based Herbicides

Zhang

et al. 2019

J. Agric. Food Chem.

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4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) is an important target site for discovering new bleaching herbicides. To explore novel HPPD inhibitors with excellent herbicidal activity, a series of novel N-aroyl diketone/ triketone derivatives were rationally designed by splicing active groups and bioisosterism. Bioassays revealed that most of these derivatives displayed preferable herbicidal activity against Echinochloa crus-galli (EC) at 0.045 mmol/m 2 and Abutilon juncea (AJ) at 0.090 mmol/m 2 . In particular, compound I-f was more potent compared to the commercialized compound mesotrione. Molecular docking indicated that the corresponding active molecules of target compounds and mesotrione shared similar interplay with surrounding residues, which led to a perfect interaction with the active site of Arabidopsis thaliana HPPD.

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Synthesis of N,O-acetals by net amide C N bond insertion of aldehydes into N-acyl phthalimides and N-acyl azoles

Cited by 12 publications

References 36 publications

Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

Progress in the Synthesis of N-Acyl-N,O-acetals

Discovery of N-Aroyl Diketone/Triketone Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibiting-Based Herbicides

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