Vinylogous Michael addition of nitroalkylideneoxindoles to isatylidene-malononitriles in the regio- and diastereoselective synthesis of dispirocyclopentylbisoxindoles

Satham, Lakshminarayana; Sankara, Chenikkayala Siva; Bhagat, Shweta; Namboothiri, Irishi N. N.

doi:10.1007/s12039-022-02122-5

Cited by 3 publications

(1 citation statement)

References 67 publications

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“…Copper-catalyzed hydroboration of these compounds was also reported by Moro et al 15 . According to other reports, 3-alkenyl oxindoles could easily converted to dispirooxindoles 16 – 21 . For example, the synthesis of dispirocyclopentanebisoxindoles via sequential Michael-aldol reaction of 3-alkenyl oxindoles was reported by Yan et al 22 .…”

Section: Introductionmentioning

confidence: 87%

Regio- and diastereoselective synthesis of thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Aghamiri,

Moghaddam,

Badpa

et al. 2024

Sci Rep

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In this publication, we reported a regio-, diastereoselective, and kinetically controlled reaction for synthesizing thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles. Obtaining only the kinetic thioxothiazolidin-indolin-2-one products together with their straightforward conversion to dispirocyclopentanebisoxindoles, excellent regio- and diastereoselectivity, easy reaction workup, and one-pot synthetic operation are considerable advantages of this work.

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Section: Introductionmentioning

confidence: 87%

Regio- and diastereoselective synthesis of thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Aghamiri,

Moghaddam,

Badpa

et al. 2024

Sci Rep

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Hauser‐Kraus Annulation Initiated Multi‐Cascade Reactions for Facile Access to Functionalized and Fused Oxazepines, Carbazoles and Phenanthridinediones

Sankara,

Namboothiri

2023

Chemistry A European J

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The Hauser‐Kraus (H‐K) annulation of N‐unsubstituted 3‐olefinic oxindoles with 3‐nucleophilic phthalides triggers a cascade of ring expansion and ring contraction reactions through several regioselective steps in one pot. While oxazepines were isolated in the presence of stoichiometric amounts of base at room temperature, carbazoles and phenanthridinediones were the products in the presence of excess base and microwave irradiation. Mechanistic studies guided by stepwise reactions and control experiments revealed that the isolable oxazepine intermediate, formed via ring expansion of the H‐K adduct, is the key precursor to carbazole and phenanthridinedione via decarboxylative regioselective cyclizations.

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Regio- and diastereoselective synthesis of thioxothiazolidin- indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Aghamiri,

Moghaddam,

Badpa

et al. 2024

Preprint

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show abstract

Vinylogous Michael addition of nitroalkylideneoxindoles to isatylidene-malononitriles in the regio- and diastereoselective synthesis of dispirocyclopentylbisoxindoles

Cited by 3 publications

References 67 publications

Regio- and diastereoselective synthesis of thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Regio- and diastereoselective synthesis of thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Hauser‐Kraus Annulation Initiated Multi‐Cascade Reactions for Facile Access to Functionalized and Fused Oxazepines, Carbazoles and Phenanthridinediones

Regio- and diastereoselective synthesis of thioxothiazolidin- indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

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