16750-42-8Relevant articles and documents
Metabolism of the Insecticide Phoxim in Plants and Cell Suspension Cultures of Soybean
Hoehl, Hans-Ulrich,Barz, Wolfgang
, p. 1052 - 1056 (1995)
The metabolism of phoxim (Z-α-imino>phenylacetonitrile), Volaton, was investigated using heterotrophic cell suspension cultures of soybean (Glycine max L.) and isolated organs (roots, stems, cotyledons, and leaves) of aseptically grown soybean plants.In both systems phoxim was first hydrolyzed to the corresponding oxime, which was then reduced to a primary nitrile amine.The primary amino group was N-malonylated as the terminal step of the catabolic sequence.The structure of this terminal metabolite was elucidated by spectroscopic (UV, IR, NMR, and MS) methods and chemical synthesis.In the plant no organ-specific differences in phoxim metabolism were observed.In the cell culture system phoxim was quantitatively converted to the N-malonate within 18-20 h, whereas in plant organs such extensive conversion could not be observed even within incubation times of about 5 days.The N-malonate was found to be excreted from the cultured cells into the medium; this effect could not be shown for the plant tissues.Keywords: Organothiophosphate metabolism; soybean plants and cell suspension cultures; conjugation reactions; N-malonylation; O-glucoside formation
Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles
Basha, Mushkin,Belema, Makonen,Dhar, T. G. Murali,Gupta, Anuradha,Gupta, Arun Kumar,Indasi, Gopi Kumar,Karmakar, Ananta,Mathur, Arvind,Meanwell, Nicholas A.,Ramalingam, Sridharan,Rampulla, Richard
supporting information, p. 441 - 449 (2020/01/23)
An efficient and practical synthetic protocol for the synthesis of 1,4-disubstituted pyrrolo[1,2- a ]pyrazine derivatives is described that originates from α-substituted pyrroloacetonitriles which, in turn, are readily available from aryl and alkyl aldehydes. The α-pyrroloacetonitriles were subjected to a Friedel-Crafts acylation with methyl chlorooxoacetate followed by reduction of the nitrile group under Pd-catalyzed hydrogenation conditions and finally aromatization with DDQ leading to the desired pyrrolo[1,2- a ]pyrazine derivatives. This method was generalized and successfully applied to various aryl, heteroaryl, and alkyl substrates. The developed protocol provides direct and convenient access to 1,4-disubstituted ring systems in moderate to good overall yields (51-68percent) without the need for purification of the intermediates. Further functionalization via the stepwise halogenation (bromination, iodination) and nitration was also demonstrated. In addition, the potential of the ester functionality for elaboration was demonstrated by manipulating into heterocyclic ring systems, exemplified by conversion into benzoxazole derivatives.
Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia
Li, Qing-Hua,Li, Zhao-Feng,Tao, Jing,Li, Wan-Fang,Ren, Li-Qing,Li, Qian,Peng, Yun-Gui,Liu, Tang-Lin
supporting information, p. 8429 - 8433 (2019/10/14)
α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.