39030-46-1Relevant articles and documents
Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
Yu, Chen-Sheng,Wang, Qiao,Bajsa-Hirschel, Joanna,Cantrell, Charles L.,Duke, Stephen O.,Liu, Xing-Hai
, p. 6423 - 6430 (2021/06/28)
Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure-activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.
Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives
Kaur, Navpreet,Singh, Priyanka,Banerjee, Prabal
supporting information, p. 2813 - 2824 (2021/04/21)
Herein, we report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol exhibits good functional group tolerance and provides a straightforward method to access spiro-imidazolidinone-cyclohexadienones. In follow-up chemistry, we have shown the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas. (Figure presented.).
Palladium-catalyzed regio- And stereoselective access to allyl ureas/carbamates: Facile synthesis of imidazolidinones and oxazepinones
Banerjee, Prabal,Saha, Debarshi,Taily, Irshad Maajid
supporting information, p. 6564 - 6570 (2020/11/10)
Typically, transition metal catalysis enforces the stereodefined outcome of a reaction. Here we disclose the palladium-catalyzed regio- and stereoselective access to allylic ureas/carbamates and their further exploitation to diverse cyclic structures under operationally simple reaction conditions. This protocol features palladium-catalyzed decarboxylative amidation of highly modular VECs with good to excellent yield, minimal waste production, wide substrate scope, and low catalyst loading. In follow-up chemistry, we demonstrated the debenzylation of vinylic imidazolidinones to N-hydroxycyclic ureas and regioselective derivatization towards the facile synthesis of halohydrins and oxiranes under mild reaction conditions in good to excellent yields. This journal is