Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1246, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2021.131155
Keywords
Gossypol; Tosylation; Tautomerism; HPLC; FT-IR; UV-Vis
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The sulfonylation of gossypol was conducted with stepwise increase of tosyl chloride content in the presence of 4-methoxypyridine N-oxide and triethylamine. It was found that 4-methoxypyridine N-oxide is a more effective catalyst compared to triethylamine, allowing selective tosylation of gossypol to 7,7'-ditosyloxygossypol. The study also investigated the structure and tautomeric equilibria of the obtained product in dichloromethane, showing that a dilactol tautomeric form is more preferable for 7,7'-ditosyloxygossypol.
Sulfonylation of gossypol with stepwise increase of tosyl chloride content in the presence of 4-methoxypyridine N-oxide and triethylamine was carried out. The sequence of gossypol's hydroxyl groups tosylation was studied using HPLC, FT-IR and UV-Vis spectroscopy. It was shown that 4-methoxypyridine N-oxide is a much more effective catalyst compared to triethylamine, and its use allows to selectively tosylate gossypol to 7,7'-ditosyloxygossypol. The structure and tautomeric equilibria of obtained 7,7'- ditosyloxygossypol in dichloromethane were studied using FT-IR, UV-Vis, H-1, C-13 and H-1-H-1 COSY NMR, Mass spectroscopy, and quantum chemistry methods. It was found that dilactol tautomeric form is more preferable for 7,7'-ditosyloxygossypol in dichloromethane, contrary to gossypol. It was proven that the combined use of triethylamine and 4-methoxypyridine N-oxide allows to tosylate different hydroxyl groups of gossypol. (C) 2021 Elsevier B.V. All rights reserved.
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