New tandem reductive rearrangement of 3-furylphthalides into 3-(3-oxoalkyl)isocoumarins

Shpuntov, Pavel M.; Shcherbinin, Vitaly A.; Абаев, Владимир Т.; Бутин, А. В.

doi:10.1016/j.tetlet.2016.02.072

Cited by 14 publications

(4 citation statements)

References 23 publications

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“…[21] Abaev et al developed a method for the rearrangement of 3-furylphtalides into 3-(3-oxoalkyl)isocoumarins using iodide generated by the hydrolysis of PI 3 , which was in turn produced from red phosphorus (P red ) and iodine (I 2 ). [22] Pre-formed HI did not improve the yield while the reaction was more efficient in aqueous media. Most examples could be reductively rearranged with good yields, except for nitro-containing substrate that was partially reduced (Scheme 6a).…”

Section: Reduction Of Cà O Bondsmentioning

confidence: 96%

“…Abaev et al. developed a method for the rearrangement of 3‐furylphtalides into 3‐(3‐oxoalkyl)isocoumarins using iodide generated by the hydrolysis of PI 3 , which was in turn produced from red phosphorus (P red ) and iodine (I 2 ) [22] . Pre‐formed HI did not improve the yield while the reaction was more efficient in aqueous media.…”

Section: Reduction Of C−o Bondsmentioning

confidence: 99%

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Iodine and Iodide in Reductive Transformations

2023

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This review provides a comprehensive overview of strategies and methodologies for reducing CÀ O and heteroatomicÀ oxygen bonds (NÀ O, SÀ O, PÀ O) using I 2 /I À , as well as other synthetically relevant bonds such as CÀ C, NÀ N, CÀ N, CÀ X, CÀ S. It highlights and discusses most of the mechanistic details provided by the original authors. Selected examples of other halides (Br and Cl) as reductants are also covered.

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Section: Reduction Of Cà O Bondsmentioning

confidence: 96%

Section: Reduction Of C−o Bondsmentioning

confidence: 99%

Iodine and Iodide in Reductive Transformations

2023

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“…This type of acid‐catalysed rearrangement of allylic alcohol to the corresponding saturated ketone has been previously reported. [2f], …”

Section: Resultsmentioning

confidence: 99%

Hetero‐Diels–Alder and Ring‐Opening Reactions of Furans Applied to the Synthesis of Functionalized Heterocycles

et al. 2017

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Furans have been explored as a scaffold for the synthesis of a range of heterocyclic compounds, exploring their dienophilic behaviour towards nitroso‐ and azoalkenes as the first step. Acid‐catalysed rearrangements of these cycloadducts, 4a,7a‐dihydro‐4H‐furo[2,3‐e][1,2]oxazines and 1,4,4a,7a‐tetrahydrofuro[3,2‐c]pyridazines, were studied. Using 1 equiv. of TFA, the bicyclic heterocycles derived from furan and 2‐methylfuran were converted into furans bearing side‐chains incorporating oxime and hydrazone groups by ring‐opening of the six‐membered ring with the concomitant aromatization of the furan ring. The use of TFA as solvent led to rearrangement via spirocyclic intermediates, followed by furan ring‐opening to afford functionalized isoxazoles or pyrazoles. Furthermore, furo‐oxazines derived from 2,5‐dimethylfuran, in which furan aromatization is precluded, were converted efficiently into 6H‐1,2‐oxazines through a furan ring‐opening reaction upon thermolysis in the presence of a catalytic amount of p‐toluenesulfonic acid. The tetrahydrofuro[3,2‐c]pyridazines derived from furan and dimethylfuran underwent acid‐catalysed addition reactions, leading to 6‐substituted hexahydrofuro[3,2‐c]pyridazines, when in the presence of alcohols or water.

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“…природным бутилизокумаринам [8]. Так как противогрибковые свойства этого класса кетонов не были известны, целью нашего исследования стало определение чувствительности полевых культур плесневых грибов Aspergillus к антимикотическим препаратам разных групп и сравнение с противогрибковой активностью полученных производных бутилизокумарина.…”

Section: Fig 1 Representatives Of Natural Butyl Isocoumarinsunclassified

Sensitivity of Fungal Microbe Aspergillus niger to New Synthetic Analogs of Natural Isocoumarin Antibiotics

Abaev,

Kachmazov,

Gutnov

et al. 2024

A&Ch

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The sensitivity of ﬁeld cultures of fungal microbe Aspergillus niger to new synthetic analogs of natural antifungal antibiotics of the isocoumarin class was determined in comparison with antimycotic activity of known drugs. The minimal mycocidal concentration (MMCC) and minimal mycostatic concentration (MMSC) of the drugs were documented. The inhibitory eﬀect (IE) was expressed as the ratio of the average colony diameter of experimental samples to the average colony diameter of control samples. From the results presented in the present work, it follows that the investigated ﬁeld cultures of Aspergillus niger are most sensitive to antimycotic drugs belonging to N-methylnaphthylmethylamine derivatives and polyene antimycotics — terbinaﬁne (MMSC = 0–2 µg/cm3) and nystatin (MMSC = 4–8 µg/cm3, IE-1 = 1.69, IE-K2 = 1.51), which have a pronounced mycocidal eﬀect. Other studied preparations, including synthesized analogues of natural isocoumarins, showed only mycostatic eﬀect on cultures of fungal microbe Aspergillus niger: ﬂuconazole — MMSC = more than 64 µg/cm3, IE-K1 = 3.38, IE-K2 = 2.52; griseofulvin — MMSC = more than 64 µg/cm3, IE-K1 = 1.79, IE-K2 = 1.53; 3-(3-oxobutyl)-isocoumarin — MMSC = more than 64 µg/cm3, IE-K1 = 1.27, IE-K2 = 1.07; 7-ﬂuoro-3-(oxobutyl)-1-N-isochromene-1-one — MMSC = greater than 64 µg/cm3, IE-K1 = 1.28, IE-K2 = 1.03; (E)-3-(3-oxobutyl-1-en-1-yl)-1-N-isochromene-1-one — MMSC = greater than 64 µg/cm3, IE-K1 = 1.12, IE-K2 = 1.06; 3-(3,3-diﬂuorobutyl)-1-N-iso-chromene-1-one — MMSC = greater than 64 µg/cm3, IE-K1 = 1.34, IE-K2 = 1.25.

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New tandem reductive rearrangement of 3-furylphthalides into 3-(3-oxoalkyl)isocoumarins

Cited by 14 publications

References 23 publications

Iodine and Iodide in Reductive Transformations

Iodine and Iodide in Reductive Transformations

Hetero‐Diels–Alder and Ring‐Opening Reactions of Furans Applied to the Synthesis of Functionalized Heterocycles

Sensitivity of Fungal Microbe Aspergillus niger to New Synthetic Analogs of Natural Isocoumarin Antibiotics

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