Reduction of Oximes and Hydrazones: Asymmetric and Diastereoselective Approaches

Ribeiro, João L. P.; Alves, Cláudia; Cardoso, António J. Marques; Lopes, Susana M. M.; Melo, Teresa M. V. D. Pinho e

doi:10.2174/1385272825666210706151631

Cited by 5 publications

(2 citation statements)

References 115 publications

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“…The synthesis of key intermediate (E)-O-methyl-N-(4-phenylbut-3-en-2-yl) hydroxylamine 5 is shown in Scheme 1, which was successfully synthesized without any purification according to a simple three-step reaction, followed by the Wittig reaction, 34,35 oxime formation reaction, and reduction reaction individually. 36 First, various substitution types of benzaldehyde 1 was treated with triphenylphosphoranylidene-2-propanone using 2 to afford intermediate 3. (Difluoromethyl)-1-methylpyrazole-4-carboxylic chloride was purchased directly.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Design, Synthesis, and Fungicidal Evaluation of Novel N-Methoxy Pyrazole-4-Carboxamides as Potent Succinate Dehydrogenase Inhibitors

Liu

Dong

et al. 2023

J. Agric. Food Chem.

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Succinate dehydrogenase (SDH, EC 1.3.5.1, also known as complex II) has been recognized as one of the most promising targets of fungicides. Here, based on the binding mode of pydiflumetofen with SDH, the carbon–carbon double bond was introduced into the chemical of pydiflumetofen and then produced the target compounds 6a–6o. The enzymatic inhibitory activity and structure–activity relationship (SAR) study showed that the 2-position and 4-position in terminal benzene were positive to increasing activity. Furthermore, fungicidal activity results in greenhouses indicated that compound 6o showed good control effects against wheat powdery mildew (WPM), cucumber powdery mildew (CPM), and southern corn rust (SCR), showing its broad-spectrum property. Especially, compound 6o exhibited 95 and 75% control effects against CPM and SCR at 6.25 mg/L, respectively, which are better than pydiflumetofen (80% control effects against CPM and 15% against SCR), indicating its potency that is worthy of further development.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Design, Synthesis, and Fungicidal Evaluation of Novel N-Methoxy Pyrazole-4-Carboxamides as Potent Succinate Dehydrogenase Inhibitors

Liu

Dong

et al. 2023

J. Agric. Food Chem.

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“…These tryptamine derivatives were used in the synthesis of 3-triazolyl- and 3-tetrazolyl-β-carbolines via Pictet–Spengler condensation followed by an oxidative step. ß -Carboline derivatives obtained by this strategy have shown interesting anticancer properties ( Panice et al, 2019 ; Ribeiro et al, 2021 ; Ribeiro et al, 2022 ).…”

Section: Introductionmentioning

confidence: 99%

Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]carbazole: an experimental and theoretical study

et al. 2023

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Nitrosoalkenes react with 8-methyl-1,6-dihydropyrrolo[3,2-c]carbazole to give both 2- and 3-alkylated products via hetero-Diels-Alder reaction followed by the cycloadduct ring-opening. Quantum chemical calculations, at DFT level of theory, were carried out to investigate the regioselectivity of the cycloaddition of ethyl nitrosoacrylate with 1,6-dihydropyrrolo[3,2-c]carbazoles as well as with pyrrole and indole, allowing a more comprehensive analysis of the reactivity pattern of nitrosoalkenes with five-membered heterocycles. Furthermore, theoretical calculations confirmed that ethyl nitrosoacrylate reacts with these heterocycles via a LUMOheterodiene-HOMOdienophile controlled cycloaddition. The reactivity of one of the oxime-functionalized 1,6-dihydropyrrolo[3,2-c]carbazole was explored and a new hexahydropyrido[4′,3':4,5]pyrrolo[3,2-c]carbazole system was obtained in high yield via a one-pot, two-step procedure.

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Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines

et al. 2022

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Hitherto unknown bis(β‐oximinoalkyl)malonates were demonstrated to be convenient platforms for the synthesis of saturated N‐heterocycles. Upon heterogeneous catalytic hydrogenation, these dioximes undergo reductive cyclization to give substituted piperidine‐4,4’‐dicarboxylates, which are valuable building blocks in medicinal chemistry. By using dioximes bearing an additional ester group in the side chain, tandem piperidine/pyrrolidinone ring closure leading to indolizidinone framework was showcased in this work. A modular synthesis of initial bis(β‐oximinoalkyl)malonates (both symmetrically and unsymmetrically substituted) was accomplished via a sequential Michael addition of two nitrosoalkene molecules to malonic ester. The mechanism of the reductive cyclization of dioximes to piperidines was investigated by isotope scrambling experiments and isolation of intermediates.

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Reduction of Oximes and Hydrazones: Asymmetric and Diastereoselective Approaches

Cited by 5 publications

References 115 publications

Design, Synthesis, and Fungicidal Evaluation of Novel N-Methoxy Pyrazole-4-Carboxamides as Potent Succinate Dehydrogenase Inhibitors

Design, Synthesis, and Fungicidal Evaluation of Novel N-Methoxy Pyrazole-4-Carboxamides as Potent Succinate Dehydrogenase Inhibitors

Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]carbazole: an experimental and theoretical study

Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines

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