2537-48-6Relevant articles and documents
One-step Synthesis of Stabilized Phosphonates
Kandil, Ali A.,Porter, Terence M.,Slessor, Keith N.
, p. 411 - 413 (1987)
Phosphonates possessing α-electron withdrawing functionalities can be readily prepared by treatment of nitriles, nitroalkanes, and esters with 2 molar equivalents of base followed by phosphonylation with diethyl chlorophosphate.
Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters
Ciszewski, Lukasz W.,Durka, Jakub,Gryko, Dorota
supporting information, p. 7028 - 7032 (2019/09/12)
This article describes the photoalkylation of electron-rich aromatic compounds with diazo esters. C-2-alkylated indoles and pyrroles are obtained with good yields even though the photocatalyst loading is as low as 0.075 mol %. For EWG-substituted substrates, the addition of a catalytic amount of N,N-dimethyl-4-methoxyaniline is required. Both EWG-EWG- and EWG-EDG-substituted diazo esters are suitable as alkylating agents. The reaction selectivity and mechanistic experiments suggest that carbenes/carbenoid intermediates are not involved in the reaction pathway.
Design, synthesis and SAR study of novel sulfonylureas containing an alkenyl moiety
Wei, Wei,Cheng, Dandan,Liu, Jingbo,Li, Yuxin,Ma, Yi,Li, Yonghong,Yu, Shujing,Zhang, Xiao,Li, Zhengming
, p. 8356 - 8366 (2016/09/09)
A series of sulfonylurea compounds was designed and synthesized via introducing an alkenyl moiety into the aryl-5 position and most title compounds exhibited enhanced antifungal activities and limited herbicidal activities compared with chlorsulfuron. Then, a CoMSIA calculation for antifungal activities was carried out to establish a 3D-QSAR model in which a cross-validated q2 of 0.585 and a correlation coefficient r2 of 0.989 were obtained. The derived model revealed that hydrophobic and electrostatic fields were the two most important factors for antifungal activity. Structure optimization was performed according to the CoMSIA model and compound 9z was found to be as potent as chlorothalonil in vitro against C. cornigerum, the pathogen of the wheat sharp eyespot disease. In order to study the fungicidal mechanism, 9z was successfully docked into yeast AHAS using a flexible molecular docking method and the resulting binding pattern was similar to that of chlorimuron-ethyl, indicating that the antifungal activity of compounds 9 was probably due to the inhibition of fungal AHAS.
Truncated borrelidin analogues: Synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation
Gündemir-Durmaz, Tülay,Schmid, Fabian,El Baz, Yana,H?usser, Annette,Schneider, Carmen,Bilitewski, Ursula,Rauhut, Guntram,Garnier, Delphine,Baro, Angelika,Laschat, Sabine
supporting information, p. 8261 - 8269 (2016/09/09)
The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.
