SYNTHESIS AND STRUCTURE OF O-ARYLSULFONYL- β-(MORPHOLIN-1-YL)PROPIOAMIDOXIMES

Abstract

Stable aromatic and heteroaromatic sulfonilamidoximes are known. But there are reports that under certain conditions this class of compounds is able to undergo rearrangements: Boulton-Katritsky under the influence of ethereal HCl to form chlorides of 2-amino-4,5-dihydrospyropyrazolylammoniums, Tiemann upon exposure to bases to form N-substituted cyanamides and ureas. Also, when UV radiation is applied to O-arylsulfonyl aromatic and heteroaromatic amidoximes, sulfonyl and imine radicals are formed. They can serve as new potential photo-splitters of amino acids. With double-stranded DNA splitting damage is difficult to repair. This can provoke self-programmed cell death and makes such an approach as effective tool for cancer treatment. Sulfonilamidoximes possess anti-oxidant and antiparasitic activity, anti-leishmanial, including. The reaction of β-(morpholin-1-yl) propiomidoximes with aromatic sulfochlorides (XC6H4SO2Cl, X = p-CH3O, p-CH3, H, p-Br, p-Cl, p-NO2) was carried out in chloroform at room temperature for 2–6 days in the presence of triethylamine. We synthesized previously unknown O-arylsulfonyl-β-(morpholin-1-yl)propioamidoximes. An evidence of their structure is fulfilled with the help of physicochemical and spectral data [IR and NMR spectroscopy (1H and 13C)]. The products are isolated with the yields: 37–53%.

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