59-49-4Relevant articles and documents
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Atkinson,Rees
, p. 1230 (1967)
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Synthesis of N-Thietan-3-yl-α-oxo Nitrogen Heterocycles from Imino Thioethers. A Novel Transformation
Press, Jeffery B.,McNally, James J.,Hajos, Zoltan G.,Sawyers, Rebecca A.
, p. 6335 - 6339 (1992)
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Design, synthesis, and docking studies of new 2-benzoxazolinone derivatives as anti-HIV-1 agents
Safakish, Mahdieh,Hajimahdi, Zahra,Zabihollahi, Rezvan,Aghasadeghi, Mohammad R.,Vahabpour, Rouhoullah,Zarghi, Afshin
, p. 2718 - 2726 (2017)
A new class of 2-benzoxazolinone derivatives was designed and synthesized for its anti-human immunodeficiency virus-1 activity. The benzoxazolinone scaffold could be replaced with catechol moiety in the potent but toxic integrase strand transfer inhibitors. The biological evaluation of the synthesized compounds revealed that all compounds were active against human immunodeficiency virus-1 at 100 μM. It is also found that most of the compounds presented no significant cytotoxicity at concentration of 100 μM. The most potent compound with thiadiazole ring as the linker inhibited the human immunodeficiency virus-1 with 84% rate. Docking of this structure in the active site of prototype foamy virus integrase indicated that the chelation of two Mg2+ cations might be the probable mechanism of the anti-human immunodeficiency virus-1 activity. Our results indicated that the synthesized compounds can provide a very good basis for the development of new anti-human immunodeficiency virus-1 agents.
Chain Walking as a Strategy for Iridium-Catalyzed Migratory Amidation of Alkenyl Alcohols to Access α-Amino Ketones
Baek, Seung Beom,Chang, Sukbok,Hwang, Yeongyu,Kim, Dongwook
supporting information, p. 4277 - 4285 (2022/03/08)
Catalytic carbon-nitrogen bond formation in hydrocarbons is an appealing synthetic tool to access valuable nitrogen-containing compounds. Although a number of synthetic approaches have been developed to construct a bifunctional α-amino carbonyl scaffold in this realm, installation of an amino functionality at the remote and unfunctionalized aliphatic sites remains underdeveloped. Here we present a tandem iridium catalysis that enables the redox-relay amidation of alkenyl alcohols via chain walking and metal-nitrenoid transfer, which eventually offers a new route to various α-amino ketones with excellent regioselectivity. The virtue of this transformation is that an unrefined isomeric mixture of alkenyl alcohols can be utilized as the readily available starting materials to lead to the regioconvergent amidation. Mechanistic investigations revealed that the reaction proceeds via a tandem process involving two key components of redox-relay chain walking and intermolecular nitrenoid transfer with the assistance of hydrogen bonding, thus representing the competence of Ir catalysis for the olefin migratory C-N coupling with high efficiency and exquisite selectivity.
Enzyme-Inspired Lysine-Modified Carbon Quantum Dots Performing Carbonylation Using Urea and a Cascade Reaction for Synthesizing 2-Benzoxazolinone
Hasani, Morteza,Kalhor, Hamid R.
, p. 10778 - 10788 (2021/09/08)
Catalysts as the dynamo of chemical reactions along with solvents play paramount roles in organic transformations in long-lasting modes. Thus, developing effective and biobased catalysts in nontoxic solvents is highly in demand. In this report, carbon quantum dots (CQDs) functionalized with-lysine (Lys-CQDs) were generated from entirely nature-derived materials; they were demonstrated to be a promising catalyst for C-N bond formation in choline chloride urea (ChCl/U), a natural deep eutectic solvent (NADES). Among a number of synthesized CQDs, Lys-CQD turned out to be a powerful catalyst in the model reaction with aniline to afford phenyl urea. This type of transformation is important because aniline as a nucleophile has low activity, and urea is a very weak electrophile but an abundant natural source of the carbonyl moiety at the same time. The optimized reaction was performed under a highly desirable condition without using tedious and toxic workup processes at a low temperature (37 °C for aliphatic amines and 60 °C for aniline derivatives), as well as by embracing the broad scope of products in good to high yields even with weak nucleophiles such as aniline. A proposed acid-activated mechanism was suggested for the model reaction that was further confirmed by detecting ammonia as the leaving group. To show further multifunctionality of the catalyst, a cascade catalysis approach was developed for synthesizing 2-benzoxazolinone, which was furnished in a two-step transformation, starting from 2-aminophenol. Using X-ray crystallography, the structure of the final product in the cascade reaction was also determined. The catalyst was characterized using various analytical techniques including SEM, TEM, AFM, XRD, IR spectroscopy, UV-vis spectroscopy, DLS, and fluorescence spectroscopy. Measuring the acid/base sites by back titration, the catalyst was shown to be highly functionalized by the lysine functional group. The size of the catalyst was determined to be in the range of 1-8 nm, having a well-dispersed surface. In all, Lys-modified CQD, as a metal-free catalyst, was synthesized, characterized, and optimized for carbonylation, as well as a cascade reaction, under mild conditions. The whole process including catalyst synthesis and organic transformations is economically competitive and fulfills all requirements toward viability.
Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone
Baxendale, Ian R.,Gambacorta, Guido
, (2022/02/01)
A continuous-flow preparation of 2-benzoxazolinone via the Hofmann rearrangement of salicylamide has been implemented employing trichloroisocyanuric acid as the stable and atom-economic chlorinating agent. The system was optimized to avoid solid accumulation and allow the preparation of hundreds of grams of the pure desired material over a working day. Furthermore, a trichloroisocyanuric acid (TCCA)-based chlorination of 2-benzoxazolone to the corresponding 5-chloro derivative was also carried out under batch conditions.