26348-46-9Relevant academic research and scientific papers
Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds
Yang, Tonghao,Lin, Yajun,Yang, Chaoqun,Yu, Wei
supporting information, p. 6097 - 6102 (2019/11/20)
Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.
Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
Yang, Tonghao,Fan, Xing,Zhao, Xiaopeng,Yu, Wei
supporting information, p. 1875 - 1879 (2018/04/16)
This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.
Stereoselective synthesis of dehydroamino acids using malonic acid half oxyester and aromatic aldehydes
Singjunla, Yuttapong,Colombano, Silvia,Baudoux, Jér?me,Rouden, Jacques
, p. 2369 - 2375 (2016/04/26)
An efficient and direct approach was developed for the synthesis of α,β-dehydroamino acid derivatives with a broad range of substrates. Amido-substituted Malonic Acid Half Oxyesters (MAHOs) have proven to be excellent partners of various aromatic aldehyde
An usual behaviour of ethers in presence of azlactones under ultrasound irradiation to give esters
Rajaram, S.,Lalitha, N.,Iyengar, D. S.
, p. 761 - 763 (2007/10/03)
The phenomenon of ester formation from ethers and azlactones under sonolysis has been observed.
A new methodology for the synthesis of N-acylaminocinnamates
Rao, Ch. Chennakesava,Lalitha, Nagubandi
, p. 3 (2007/10/02)
A new synthesis of biologically active N-protected amino acids (2) and amides (4) from 4-ylidene-5(4H)-oxazolones (1) is described.
Reactions of Some 1,3-Diaminonucleophiles with Azlactones
Tikdari, Ahmad M.,Tripathy, Pradeep K.,Mukerjee, Arya K.
, p. 1659 - 1662 (2007/10/02)
Triethylamine-mediated reactions of S-substituted isothiuronium halides (2) with unsaturated azlactones (1) gave the corresponding S-substituted 2-thiopyrimidines (3), S-substituted 3-thioacrylanilide (10), and 4-benzylidene-2-iminoimidazolidin-5-one (13)
