Indium-Catalyzed Intramolecular Hydroamidation of Alkynes: An <i>Exo</i>-<i>Dig</i> Cyclization for the Synthesis of Pyranoquinolines through Post-Transformational Reaction

Balalaie, Saeed; Mirzaie, Sattar; Nikbakht, Ali; Hamdan, Fatima; Röminger, Frank; Navari, Razieh; Bijanzadeh, Hamid Reza

doi:10.1021/acs.orglett.7b02603

Cited by 29 publications

(12 citation statements)

References 51 publications

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“…In 2017, Balalaie and co‐workers found that indium(III) chloride activated triple bond and intramolecular hydroamidation of alkynes followed by cyclization yielded pyranoquinolines 85 a – l from the corresponding alkynes 84 a – l (Scheme 23). [57] The cyclization of the amide through oxygen occurred via 6‐exo‐dig that led to the pyran ring and the role of nitrogen in the quinoline was very crucial due to stability and formation of In‐complex with the triple bond.…”

Section: Incl3 Catalyzed Activation Of C−c Triple Bondsmentioning

confidence: 99%

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Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

ChemistrySelect

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This review summarizes recent advances of indium trichloride catalyzed synthesis of different organic compounds. It is obvious that InCl3 co‐ordinates with C−C and/or C‐heteroatom multiple bonds and thereby makes them very prone to nucleophilic attack to form a new bond. This Lewis acid catalyst also activates oxiranes to produce aldehydes. Multicomponent synthesis including C−C bond formation reaction and construction of N, O and S‐containing heterocycles are discussed in organic solvents as well as in water. This article highlights recent developments and application of indium(III) chloride as a catalyst in organic synthesis from 2015 to 2020. The mechanism of few important reactions is discussed in detail which will be very useful for the readers.

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Section: Incl3 Catalyzed Activation Of C−c Triple Bondsmentioning

confidence: 99%

“…Mechanistically (Scheme 23). [57] The cyclization of the amide through oxygen occurred via 6-exo-dig that led to the pyran ring and the role of nitrogen in the quinoline was very crucial due to stability and formation of In-complex with the triple bond.…”

Section: Chemistryselectmentioning

confidence: 99%

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

ChemistrySelect

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“…Balalaie et al (Balalaie et al, 2017b ) have reported a diversity-oriented access to isoxazolino-benzazepines 22b and isoxazolo-benzazepines 22d in good to excellent yields and with high diastereoselectivities (≈95) via post-Ugi heteroannulation reaction involving intramolecular 1,3-dipolar cycloaddition of 2-((hydroxyimino)methyl)benzoic acid 22a and 22c , respectively. The nitrile oxide reacted with alkenes or alkynes in the presence of sodium hypochlorite (NaOCl) in DCM at rt (Scheme 10 ).…”

Section: Fused Heterocyclesmentioning

confidence: 99%

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates

Bariwal¹,

Kaur

Voskressensky

et al. 2018

Front. Chem.

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Multicomponent reactions (MCRs) have proved as a valuable tool for organic and medicinal chemist because of their ability to introduce a large degree of chemical diversity in the product in a single step and with high atom economy. One of the dominant MCRs is the Ugi reaction, which involves the condensation of an aldehyde (or ketone), an amine, an isonitrile, and a carboxylic acid to afford an α-acylamino carboxamide adduct. The desired Ugi-adducts may be constructed by careful selection of the building blocks, opening the door for desired post-Ugi modifications. In recent times, the post-Ugi transformation has proved an important synthetic protocol to provide a variety of heterocyclic compounds with diverse biological properties. In this review, we have discussed the significant advancements reported in the recent literature with the emphasis to highlight the concepts and synthetic applications of the derived products along with critical mechanistic aspects.

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“…These observations stimulated our interest to study the urease inhibitory activity of the DFX and some of its new derivatives for the first time and investigate the role of OH and various substituted 1,2,4‐triazole groups in the inhibition of urease activity. In this regard and continuation of our research interest in the synthesis of heterocyclic skeletons, we report an efficient procedure for the synthesis of some DFX analogs ( N ‐substituted bis‐hydroxyphenyl‐1,2,4‐triazoles), containing triazole backbone ( Scheme ). The present article, therefore, describes urease inhibitory properties of newly synthesized compounds and investigates their mode of molecular interaction to reveal the probable mechanism class of these compounds, including complexation of nickel ions, blocking the active channel site, or the possibility of covalent interaction with a cysteine residue.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking of Deferasirox and Substituted 1,2,4‐Triazole Derivatives as Novel Potent Urease Inhibitors: Proposing Repositioning Candidate

Ashani

Azizian

Alavijeh

et al. 2020

Chemistry & Biodiversity

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A series of new deferasirox derivatives were synthesized through the reaction of monosubstituted hydrazides with 2-(2-hydroxyphenyl)-4H-benzo[e] [1,3]oxazin-4-one. For the first time, deferasirox and some of its derivatives were evaluated for their in vitro inhibitory activity against Jack bean urease. The potencies of the members of this class of compounds are higher than that of acetohydroxamic acid. Two compounds, bearing tetrazole and hydrazine derivatives (bioisoester of carboxylate group), represented the most potent urease inhibitory activity with IC 50 values of 1.268 and 3.254 μM, respectively. In silico docking studies were performed to delineate possible binding modes of the compounds with the enzyme, urease. Docking analysis suggests that the synthesized compounds were anchored well in the catalytic site and extending to the entrance of binding pocket and thus restrict the mobility of the flap by interacting with its crucial amino acid residues, CME592 and His593. The overall results of urease inhibition have shown that these target compounds can be further optimized and developed as a lead skeleton for the discovery of novel urease inhibitors Figure 1. The structure of DFX and its complexation with iron.Scheme 5. The proposed reaction mechanism for the synthesis of DFX and its analogs 7a -7e. two ionic bonds with two Ni 2 + ions. Also, the binding mode of DFX was depicted in Figure 4b, which revealed that like AHA carboxylate group pointed to the bi-nickel ion center. Besides, DFX formed a π -π Figure 2. The location of JBU active site over C-terminal (αβ) 8 TIM barrel domain (a), close-up representation of the active site, the AHA co-crystallized, and the corresponding re-docked form are represented in green and cyan color, respectively (b).Figure 3. Representation of two different docking poses of compounds relative to bi-nickel center over JBU active site: Compounds with 1,2,4-triazole-N 1 -substituted oriented toward the metal center (a), and compounds with 2-hydroxyphenyl pointed one (b). 3,5bis(2-hydroxyphenyl) moiety, related N 1 -substitution and 1,2,4-triazole ring are shown in red, yellow, and navy, respectively.

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Indium-Catalyzed Intramolecular Hydroamidation of Alkynes: An Exo-Dig Cyclization for the Synthesis of Pyranoquinolines through Post-Transformational Reaction

Cited by 29 publications

References 51 publications

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates

Synthesis, Biological Evaluation and Molecular Docking of Deferasirox and Substituted 1,2,4‐Triazole Derivatives as Novel Potent Urease Inhibitors: Proposing Repositioning Candidate

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