ChemInform Abstract: 4‐Phenyloxazolidin‐2‐ones and Isoindolin‐1‐ones: Chiral Auxiliaries for Diels—Alder Reactions of N‐Substituted 1,3‐Dienes.

McAlonan, Helena; Murphy, James P.; Nieuwenhuyzen, Mark; Reynolds, Karen; Sarma, P. K. S.; Stevenson, Paul J.; Thompson, Norris

doi:10.1002/chin.200221084

Cited by 4 publications

(4 citation statements)

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“…4 In view of the importance of isoindolinones, many methods have been developed to synthesize these coveted structures in the past decades, including Heck cyclization, 5 ring-closure of hydrazones, 6 exploitation of carbanion methodology, 7 and Diels–Alder approach. 8 Although there have been a few reports on the reactions of these compounds, it is still necessary to develop a general, large-scale, mild and environmentally friendly synthetic method for isoindolinones.…”

Section: Table 1 Optimization Of Synthesis Conditionsmentioning

confidence: 99%

Hectogram-Scale Synthesis of Indobufen from Diludine-Triggered Metal-Free Cascade

et al. 2023

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In this study, indobufen was successfully synthesized from diludine triggered metal-free cascade in good yield. This process includes esterification, reduction, reductive amination/ condensation cascade, hydrolysis and recrystallization. Additionally, the post-treatment procedure was greatly simplified, and indobufen can be obtained by simple recrystallization that complies with the pharmacopoeia standards. Moreover, this work will be used as a basis for further research into the efficient production of indobufen on an industrial scale.

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Section: Table 1 Optimization Of Synthesis Conditionsmentioning

confidence: 99%

Hectogram-Scale Synthesis of Indobufen from Diludine-Triggered Metal-Free Cascade

et al. 2023

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“…Initial studies by Beller and co-workers [141] on enantioselective AAD reactions were carried out with oxazolidinones as chiral auxiliaries and as amide components. Intermediate chiral N-dienyl lactams have been previously mentioned in Section 2.2.1, which were prepared by multistep synthesis [68][69][70][71]. The highest facial selectivity in the DA reaction was achieved with the phenyl substituted oxazolidinone giving adduct 113 in 94% yield and 90% de (Scheme 58).…”

Section: J O U R N a L P R E -P R O O Fmentioning

confidence: 99%

Diels-Alder reactions of 1-amino-1,3-dienes and related systems

2021

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“…In non-symmetrical preparation of some compounds from isoindolin-1-one they can introduced as building blocks for a Diels-Alder reaction [21][22][23][24][25]. Because of their multi biological properties of isoindoline derivatives, there are many chemical pathways have been reported for the preparation of these heterocycles [26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Bioactivities of Isoindolin-1-3-Phosophonate Compounds

Hamdi¹,

Jellali²,

Nasr³

et al. 2021

Preprint

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In this work an efficient synthesis of isoindolin-1-one-3-phosphonates under catalyst- and solvent-free conditions was reported to afford the desired compounds in excellent yields with potent pharmacological properties. The synthetic method involves the preparation of isoindolin-1-one-3-phosphonates by a ‘one-pot’ three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent and catalyst free-conditions. All new compounds were characterized by by 1H NMR, 13C NMR, FT-IR and elemental analysis techniques. The synthesized compounds were screened for their antimicrobial activities against gram-positive bacterial strains (Micrococcus luteus, Listeria monocytogenes, Staphylococcus aureus and Bacillus cereus), a gram-negative bacterial strain (Salmonella typhimurium) and a fungus (Candida albicans). Compound 4a was found to be the most active against antimicrobial against L. M. luteus, L. monocytogenes and C. albicans with an inhibition zone of 35, 22 and 38 mm respectively. They were additionally also investigated for their anti-parasitical activities against Leishmania major promastigotes and amastigotes and Toxoplasma gondii in vitro. The compounds 4a,b are the most active against L. major amastigotes and promastigotes with EC50 < 1 µM. Cytotoxicity investigations of the isoindolin-1-one-3-phosphonates were conducted in two human cancer cell lines, MDA-MB-231 and MCF-7 all the compounds gave anticancer activity < 1.5 µM. We can conclude that 4a is a good drug candidate for all the biological assays, further studies for SAR detection and in vivo evaluation are highly recommended.

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ChemInform Abstract: 4‐Phenyloxazolidin‐2‐ones and Isoindolin‐1‐ones: Chiral Auxiliaries for Diels—Alder Reactions of N‐Substituted 1,3‐Dienes.

Cited by 4 publications

References 1 publication

Hectogram-Scale Synthesis of Indobufen from Diludine-Triggered Metal-Free Cascade

Hectogram-Scale Synthesis of Indobufen from Diludine-Triggered Metal-Free Cascade

Diels-Alder reactions of 1-amino-1,3-dienes and related systems

In Vitro Bioactivities of Isoindolin-1-3-Phosophonate Compounds

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ChemInform Abstract: 4‐Phenyloxazolidin‐2‐ones and Isoindolin‐1‐ones: Chiral Auxiliaries for Diels—Alder Reactions of N‐Substituted 1,3‐Dienes.

Cited by 4 publications

References 1 publication

Hectogram-Scale Synthesis of Indobufen from Diludine-Triggered Metal-Free Cascade

Hectogram-Scale Synthesis of Indobufen from Diludine-Triggered Metal-Free Cascade

Diels-Alder reactions of 1-amino-1,3-dienes and related systems

In Vitro Bioactivities&nbsp;of Isoindolin-1-3-Phosophonate Compounds

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In Vitro Bioactivities of Isoindolin-1-3-Phosophonate Compounds