Reactions of 5-Arylidene-2-thiohydantoins with Halogenated Compounds and Anthranilic Acid

El‐Din, Asmaa A. Magd; Elsharabasy, Salwa A.; Hassan, Aisha Y.

doi:10.1080/104265090968677

Cited by 9 publications

(4 citation statements)

References 8 publications

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“…The transformations required long reaction times to reach completion, and the target pentacyclic BGs 69 were formed in yields from 35 to 75 %. [44] Related synthetic routes were also used for the preparation of heterocondensed pteridines with 6+5 and 6+6 BG cores, [45] imidazo-quinazolinediones with 6+5 BGs, [46] 5+6 pyrimidopyrimidinones [47] and other polycyclic 6+5 fusedring systems. [48]…”

Section: Carboxylic Acid Group Derivatives As Functional Group Xmentioning

confidence: 99%

“…The preparation of polyheterocyclic 6+6 BGs through reaction with substituted anthranilic acids under microwave irradiation conditions was reported by Domon et al in 2001. [44] Related synthetic routes were also used for the preparation of heterocondensed pteridines with 6+5 and 6+6 BG cores, [45] imidazo-quinazolinediones with 6+5 BGs, [46] 5+6 pyrimidopyrimidinones [47] and other polycyclic 6+5 fusedring systems. A year later, the same research group used this method for the synthesis of various polycondensed BG compounds based on the 6+6 BG motif.…”

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confidence: 99%

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Synthetic Strategies for Preparing Bicyclic Guanidines

Lemrová

Soural

2015

Eur J Org Chem

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Different synthetic approaches leading to compounds containing bicyclic guanidine scaffolds are summarised. Because of the diversity within this group of target molecules and the wide range of individually reported synthetic routes, this review is divided into three subsections according to the key intermediate used to obtain the bicyclic structure. The first section is dedicated to strategies in which monocyclic guanidine derivatives are used as the key intermediates. The second section presents direct syntheses of bicyclic guanidines from acyclic or non‐guanidine starting materials. The last part of the text addresses the synthesis of target compounds through the use of polymer‐supported chemistry. The applicability of each synthetic approach for the preparation of target molecules with certain x+y combinations of individual cycles is specified.

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Section: Carboxylic Acid Group Derivatives As Functional Group Xmentioning

confidence: 99%

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confidence: 99%

Synthetic Strategies for Preparing Bicyclic Guanidines

Lemrová

Soural

2015

Eur J Org Chem

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“…Alternative methods for the synthesis of functionalized thiohydantoins are based on alkylation of the sulfur atom in C5-substituted thiohydantoins with 1,3dioxolan-methylsulfate derivatives, or various chloro-and bromo-containing alkylating reagents, including phenacyl bromide. [23][24][25][26] The catalytic chemoselective S-alkylation of 5substituted thiohydantoins with trimethyl or triethyl orthoformates was shown to be accompanied by N-acetylation. [24] N3-Substituted thiohydantoins react with alkyl halides or phenacyl bromide in aqueous solution of sodium hydroxide and ethanol affording the target products in good yield.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, the reactions of N3‐substituted thiohydantoins with ethyl chloroacetate [7] or ethyl chloropropionate [22] in the presence of K 2 CO 3 afford N,N′‐disubstituted thiohydantoins. Alternative methods for the synthesis of functionalized thiohydantoins are based on alkylation of the sulfur atom in C5‐substituted thiohydantoins with 1,3‐dioxolan‐methylsulfate derivatives, or various chloro‐ and bromo‐containing alkylating reagents, including phenacyl bromide [23–26] . The catalytic chemoselective S‐alkylation of 5‐substituted thiohydantoins with trimethyl or triethyl orthoformates was shown to be accompanied by N‐acetylation [24] .…”

Section: Introductionmentioning

confidence: 99%

Regio‐ and Chemoselectivity of Tandem N‐Ketoalkylation/Cyclization of 2‐Thioxoimidazoline‐4‐One

Dorofeev,

Zhilitskaya,

Yarosh

et al. 2024

ChemistrySelect

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The reaction of 2‐thioxoimidazolidin‐4‐one (thiohydantoin) with aliphatic, aromatic and heteroaromatic α‐iodomethylketones has been investigated in the absence of bases or catalysts. The reaction proceeds as N‐alkylation with subsequent intramolecular dehydrative cyclization. A series of new mono‐ and fused bicyclic iodide and triiodide salts was obtained based on the 5‐oxo‐2‐thioxoimidazolidin‐1‐ium and imidazo[2,1‐b]thiazolium cations. The observed regioselectivity has been rationalized and the mechanism was proposed.

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Reactions of 5‐Arylidene‐2‐thiohydantoins with Halogenated Compounds and Anthranilic Acid.

2006

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Ring closure reactions O 0130Reactions of 5-Arylidene-2-thiohydantoins with Halogenated Compounds and Anthranilic Acid. -With the aim to developing new simple procedures for the synthesis of fused azoles, the reactions of arylidenethiohydantoins (I) with mono-and dihalogenated compounds are investigated. Cyclization of their reaction products is achieved by polyphosphoric acid. In addition, the behavior of ylidenemethylmercapto hydantoins (XII) and (XIV) towards the action of anthranilic acid (XI) for the synthesis of new imidazo[2,1-b]quinazolines containing 2-furyl and 2-thianyl moieties is examined. -(EL-DIN*, A. A. M.; ELSHARABASY, S. A.; HASSAN, A. Y.; Phosphorus, Sulfur Silicon Relat.

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Reactions of 5-Arylidene-2-thiohydantoins with Halogenated Compounds and Anthranilic Acid

Cited by 9 publications

References 8 publications

Synthetic Strategies for Preparing Bicyclic Guanidines

Synthetic Strategies for Preparing Bicyclic Guanidines

Regio‐ and Chemoselectivity of Tandem N‐Ketoalkylation/Cyclization of 2‐Thioxoimidazoline‐4‐One

Reactions of 5‐Arylidene‐2‐thiohydantoins with Halogenated Compounds and Anthranilic Acid.

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