Regioselective annulation of propargyl alcohols with ambident-enols: A Ca(II)-catalyzed trisubstituted benzochromene synthesis

Yaragorla, Srinivasarao; Pareek, Abhishek; Dada, Ravikrishna

doi:10.1016/j.tetlet.2017.10.077

Cited by 41 publications

(15 citation statements)

References 39 publications

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“…Initially, Ca(II) produce the ether, which then undergoes 6‐ endo iodocyclization to furnish the iodobenzochromene 37 . (Scheme ) . In this reaction, the ether intermediate was isolated and treated with iodine under the same conditions to obtain the product and thus confirms the mechanism.…”

Section: Oxygen‐containing Heterocyclic Iodidessupporting

confidence: 70%

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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Section: Oxygen‐containing Heterocyclic Iodidessupporting

confidence: 70%

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

Khan

Yaragorla

2019

Eur J Org Chem

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“…23 Similarly, iodocarbazole 2j was subjected to the Heck cross-coupling conditions with ethyl acrylate [Pd(OAc) 2 , Bu 4 NBr, K 2 CO 3 ] and the carbazole derivative 6 in 83% yield was obtained (Scheme 2). 24…”

Section: Resultsmentioning

confidence: 99%

Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration

et al. 2018

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Herein, we disclose the first report on iodo-cycloisomerization of 1-(indol-3-yl)-1-arylbut-3-yn-2-ols to form 3-iodocarbazoles. The synthesis proceeds through a cascade 5-endo-spirocyclization, followed by selective 1,2-alkyl migration. This method governs the green synthesis principles such as open-flask reaction, AcOEt as the solvent, rt reaction with short time, use of iodine, and broad substrate scope with atom and step economy.

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“…Yaragorla and co-workers in the year 2017 described a highly regioselective annulation reaction between propargyl alcohols 39 and several enols 65 using calcium triflate catalyst, under a solvent-free condition at 110 °C, Scheme 26 . 59 …”

Section: Different Catalysts Used In Propargylic Substitution Reactionsmentioning

confidence: 99%

Scope and advances in the catalytic propargylic substitution reaction

2018

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Regioselective annulation of propargyl alcohols with ambident-enols: A Ca(II)-catalyzed trisubstituted benzochromene synthesis

Cited by 41 publications

References 39 publications

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

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

Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration

Scope and advances in the catalytic propargylic substitution reaction

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