Sulfanyl 5H-dihydro-pyrrole derivatives via 1,3-dipolar cycloaddition, their further chemical manipulation and antioxidant activity

Abstract

Sulfanyl 5H-dihydropyrroles were synthesized through diastereoselective 1,3-dipolar cycloaddition of sulfanyl-substituted azomethine ylides from glycine esters to N-phenylmaleimide under thermal or Ag-catalyzed conditions. Further manipulation with DDQ afforded novel polysubstituted pyrroles which were more potent antioxidants and lipoxygenase inhibitors than their 5H-dihydro analogues.

An efficient and facile access to highly functionalized pyrrole derivatives

“…For the operational simplicity and continuity of this one-pot condensation–cycloaddition–aromatization reaction, CH 2 Cl 2 was firstly selected as solvent instead of the generally used toluene [10,25–26] for this oxidation step. Unfortunately, the desired pyrrole product 12a was obtained only in 41% yield with DDQ (4 equiv) as oxidant at room temperature for 48 h (Table 3, entry 1).…”

“…As our aim was to construct a small library of polysubstituted pyrroles for antibacterial screening, it prompted us to develop a concise and efficient synthesis of pyrrolo[3,4- c ]pyrrole-1,3-diones [8–10] via 1,3-dipolar cycloaddition without any chiral catalysts/ligands and a facile access to highly substituted pyrroles with amide groups or ester groups. Herein, we propose a straightforward and one-pot synthesis of pyrrolo[3,4- c ]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N -alkyl maleimide, followed by a facile oxidation using DDQ as oxidant.…”

Biological activity of two new pyrrole derivatives against stored-product species: influence of temperature and relative humidity

“…Two pyrrole derivatives, developed by the late Prof Dr Y. Elemes and his group (Oikonomou et al , 2015), the ethyl 3-(benzylthio)-4,6-dioxo-5-phenyl-2,4,5,6-tetrahydropyrrolo[3,4- c ]pyrrole-carboxylate (3i) and the isopropyl 3-(benzylthio)-4,6-dioxo-5-phenyl-2,4,5,6-tetrahydropyrrolo[3,4- c ]pyrrole-carboxylate (3k), were used for experimentation (fig. 1).…”

“…The codes 3i and 3k correspond to the ones given for the certain derivatives by Oikonomou et al . (2015).

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“…In this regard, members of the pyrrole group are likely to have some interesting properties that merit additional investigation as insecticides at the post-harvest stages of agricultural commodities. Recently, it was found that some new sulfanyl 5 H -dihydro-pyrrole derivatives have some certain biological activities by exhibiting strong antioxidant activity (i.e., inhibition of lipid peroxidation and soybean lipoxygenase) (Georgiou et al ., 2012; Oikonomou et al ., 2015). However, there are no published data regarding the efficacy of these compounds as insecticides so far.…”