Molecular Iodine-Mediated Cyclization of Tethered Heteroatom-Containing Alkenyl or Alkynyl Systems

Mphahlele, Malose J.

doi:10.3390/molecules14124814

Cited by 131 publications

(27 citation statements)

References 94 publications

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“…Prolonging the reaction time and increasing the iodine concentration did not improve appreciably the yields. Recently, Veisi [19] and Mphahlele [20] surveyed the applications of molecular iodine to the synthesis of a number of heterocyclic compounds that can be viewed as monomers for ROP.…”

Section: Monomers' Synthesismentioning

confidence: 99%

Molecular iodine in monomer and polymer designing

Moulay

2013

Designed Monomers and Polymers

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Not only does the molecular iodine play a leading role in organic synthesis but also in the polymer synthesis. Different kinds of polymerization initiated by molecular iodine are herein screened: cationic polymerization, radical polymerization, living/controlled radical polymerization (LCRP) such as reverse iodine transfer polymerization, polycondensation, and ring-opening polymerization (ROP). Also, the functionalization of polymers using molecular iodine, such as the acetylation of polysaccharides (cellulose, starch), and the use of iodine-polymer complex in organic synthesis are also discussed. Numerous natural and synthetic polymers are prone to make complexes with molecular iodine, and one feature of such complexes is their propensity as polymer-supported reagent and catalysts in many organic syntheses.

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Section: Monomers' Synthesismentioning

confidence: 99%

Molecular iodine in monomer and polymer designing

Moulay

2013

Designed Monomers and Polymers

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“…With those precedents in mind, herein we present the synthesis of a new series of non‐symmetric hydro‐xanthenodiones. The oxidative aromatization of the lateral rings of the heterocyclic core was also studied, being an efficient, user‐friendly procedure to generate structurally diverse compounds . Moreover, the collection of derivatives was extended preparing different amides, of high incidence in modern pharmaceuticals and biologically active compounds, by reaction of the xanthenic precursors with different amines.…”

Section: Introductionmentioning

confidence: 99%

A Synthetic Approach to PW2‐Like Compounds

et al. 2020

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The 9H-xanthene derivatives, like PW2, displayed a wide spectrum of bioactivities. Herein, we reported a rapid and simple synthetic route for compounds containing the xanthenic moiety in their structure and amides. The efficient preparation of novel 1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1-xanthen-9-ylacetic acid alkyl esters by multicomponent tandem Michaelcyclization reactions starting from cyclohexanediones and alkynes is described. Iodine and cerium (IV) ammonium nitrate were used for the oxidative aromatization step proving a series of 1,8-mono and dialkoxy-alkyl-xanthenyl-9-yl acetic acid esters in good yields. The proposed mechanism for the oxidative aromatization involves several organic transformations. The final step was the incorporation of an amide to mimic the PW2 structure that was prepared by hydrolysis of the esters, followed by the amide formation using N,N-dimethyl-1,3propandiamine, and benzylamine.

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“…The iodocyclization of carbon-carbon multiple bonds with an intramolecular nucleophilic center plays an important role in the stereoselective construction of cyclic compounds [31,32]. Synthesis of various heterocyclic compounds of biological importance by iodocyclization has been explored with a wide variety of nucleophiles, including N, O, S, Se, etc., and it has become a powerful tool for the construction of different heterocycles [33][34][35][36][37][38][39][40][41]. The cyclized products are ideal substrates for further functionalization as they contain an iodo group.…”

Section: Introductionmentioning

confidence: 99%