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• W1997741543 abstract "Hydroxylamine-O-sulfonic acid (HOSA) was used as an efficient nucleophilic amination reagent for 2-chloropyrimidines, 2-chloroquinolines, and 1-chloroisoquinoline. The newly obtained heteroaromatic hydroxylamine-O-sulfonates subjected to the reaction with acyl isothiocyanates underwent tandem nucleophilic addition–electrophilic 5-endo-trig cyclization. The mechanism of the cyclization was investigated with use of the long-range corrected hybrid density functional ωB97X-D/6-31+G∗ and SM8 (DMF) solvation model. The structures of the heteroaromatic hydroxylamine-O-sulfonates and N-(5-methoxy-2H-[1,2,4]thiadiazolo[2,3-a]pyrimidin-2-ylidene)benzamide were confirmed by single crystal X-ray analysis. N-(2H-[1,2,4]thiadiazolo[3,2-a]isoquinolin-2-ylidene)benzamide exhibited a pronounced in vitro cytostatic activity against human tumor cell lines SISO, LCLC, A-427, DAN-G, and RT-4 (IC50 in the range 1.47–2.97 μM)." @default.
• W1997741543 created "2016-06-24" @default.
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• W1997741543 date "2011-05-01" @default.
• W1997741543 modified "2023-10-17" @default.
• W1997741543 title "Synthesis of aza-aromatic hydroxylamine-O-sulfonates and their application to tandem nucleophilic addition–electrophilic 5-endo-trig cyclization" @default.
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• W1997741543 doi "https://doi.org/10.1016/j.tet.2011.03.091" @default.
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