Facile synthesis of 2-iodo-spiro[indene-1,1′-isobenzofuran]-3′-ones via iodine-promoted cascade cyclization

Zhu, Hongfei; Duan, Xue; Wang, Lijing; Zhong, Mei‐Jin; Liu, Xueyuan; Liang, Yong‐Min

doi:10.1039/c2cc36127b

Cited by 33 publications

(11 citation statements)

References 60 publications

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“…In 2012, Liang's group developed an efficient approach to 2‐iodo‐spiro[indene‐1,1′‐isobenzofuran]‐3′‐ones 95 via iodine‐mediated cascade cyclization of 2‐propynols benzoates 93 (Scheme 36). [52] Mechanistically, the reaction proceeded via the capture of allenic carbocation intermediate A by intramolecular ester and a sequential regiospecific iodocyclization in the presence of iodine. Various 2‐propynols benzoates with good functional groups were transformed into the corresponding desired products 95 in moderate to excellent yields under mild conditions.…”

Section: Reactions Involving O S‐nucleophiles To Capture Allenyl Carmentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

2020

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Heterocyclic compounds are important organic compounds and have emerged as key scaffolds in numerous drugs, natural products, vitamins, biologically and pharmaceutically active compounds. Over the past few decades, the development of versatile methodologies employing propargylic alcohols as synthons for the construction of heterocyclic skeletons has attracted great attention from synthetic chemists. In this review, recent developments in the cascade cyclization of propargylic alcohols with diverse nucleophiles to construct heterocyclic compounds are summarized. According to the types of nucleophiles, these reactions can be divided into four categories: 1) Reactions involving C‐nucleophiles to capture allenyl carbocation; 2) Reactions involving O, S‐nucleophiles to capture allenyl carbocation; 3) Reactions involving N, P‐nucleophiles to capture allenyl carbocation; 4) Reactions involving halo‐nucleophiles to capture allenyl carbocation.

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Section: Reactions Involving O S‐nucleophiles To Capture Allenyl Carmentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

2020

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“…Because of their unique physical properties and biological activity, many synthetic methods for constructing functionalized spirolactones have been developed . In general, the most common strategy for building spirolactones relies on Dieckmann condensation, Diels–Alder reactions, and ring-closing metathesis (RCM) .…”

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confidence: 99%

Synthesis of Spirolactones via a BF₃·Et₂O-Promoted Cascade Annulation of α-Keto Acids and 1,3-Enynes

Zhao

Zhang

et al. 2021

Org. Lett.

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A novel and effective method for the synthesis of spirolactones from readily available α-keto acids and 1,3-enynes is developed via a BF 3 •Et 2 O-promoted cascade annulation. This sequential process is conducted at room temperature, and it provides the functionalized spirolactones in good to excellent yield under metal-free conditions.The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.1c01827.Full experimental details and characterization data for all products (PDF)Accession CodesCCDC 2036731 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

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“…Facile synthetic approach to substituted 2‐iodospiro[indene‐1,10 ‐isobenzofuran]‐3 I ‐ones ( 65 ) is developed at r.t. via an iodine‐promoted cascade cyclization of 2‐(3‐hydroxy‐3,3‐ diary prop‐1‐yn‐1‐yl)benzoates ( 64 ) in good yields (Scheme ) . Various benzoates such as benzyl, methyl, ethyl, isopropyl and tert ‐butyls are compatible with the protocol ( 65a ).…”

Section: Oxygen‐containing Heterocyclic Iodidesmentioning

confidence: 99%

Iodocyclization of Propargyl Alcohols: Highly Facile Approach to Hetero/Carbocyclic Iodides

Khan

Yaragorla

2019

Eur J Org Chem

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Iodocyclization of propargyl alcohols is an active area for the construction of hetero/carbocyclic iodides. Ambiphilic reactivity of propargyl alcohols made it more attractive to tune their reactivity towards the development of regioselective synthetic strategies. In general, iodocyclization reactions are atom and step economic, promoted by simple and readily available inexpensive electrophilic iodine reagents at ambient temperature. These compounds find potential applications in pharmaceutical and material sciences, because of the presence of a preinstalled reactive iodide functionality. Therefore, many researchers are actively involved in developing synthetic strategies towards iodocyclizations from propargyl alcohols for various applications. In this mini‐review, we emphasize the full list of synthetic endeavors made towards the “iodocyclization of propargyl alcohols, propargyl ethers and homopropargyl alcohols”.

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Facile synthesis of 2-iodo-spiro[indene-1,1′-isobenzofuran]-3′-ones via iodine-promoted cascade cyclization

Cited by 33 publications

References 60 publications

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Synthesis of Spirolactones via a BF₃·Et₂O-Promoted Cascade Annulation of α-Keto Acids and 1,3-Enynes

Iodocyclization of Propargyl Alcohols: Highly Facile Approach to Hetero/Carbocyclic Iodides

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Facile synthesis of 2-iodo-spiro[indene-1,1′-isobenzofuran]-3′-ones via iodine-promoted cascade cyclization

Cited by 33 publications

References 60 publications

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Synthesis of Spirolactones via a BF3·Et2O-Promoted Cascade Annulation of α-Keto Acids and 1,3-Enynes

Iodocyclization of Propargyl Alcohols: Highly Facile Approach to Hetero/Carbocyclic Iodides

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Synthesis of Spirolactones via a BF₃·Et₂O-Promoted Cascade Annulation of α-Keto Acids and 1,3-Enynes