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Synthesis of dehydroabietane-derived sulfonamides with fragments of L-amino acid esters and hydrazides
- Authors: Izmest'ev E.S1, Petukhov D.V2, Pestova S.V1, Rubtsova S.A1
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Affiliations:
- Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences
- Vyatka State University
- Issue: Vol 59, No 1 (2023)
- Pages: 106-118
- Section: Articles
- URL: https://journal-vniispk.ru/0514-7492/article/view/144713
- DOI: https://doi.org/10.31857/S0514749223010093
- EDN: https://elibrary.ru/PGADBV
- ID: 144713
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Abstract
Ethyl ester of 12-chlorosulfodehydroabietic acid, when reacted with the methyl esters of glycine, methionine, leucine, glutamic acid, tyrosine, proline, histidine, for the first time yielded the corresponding sulfonamides, the ester group (-COOMe) of which was selectively transferred to the hydrazide (-COONHNH2) without affecting the ethyl group bounded with the dehydroabietic acid fragment. In the case of glutamic acid, the corresponding dihydrazides were obtained. The reaction of 12-chlorosulfodehydroabietic acid ethyl ester with cystine dimethyl ester led to the selective formation of bis-sulfonamide, while carrying out the same reaction in an acetone-contained solution was accompanied by the cleavage of the disulfide bond of the cystine fragment to give thioketal. The obtained bis-sulfonamide and thioketal were oxidized with chlorine dioxide to afford in both cases sulfochloride.
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About the authors
E. S Izmest'ev
Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences
Email: evgeniyizmestev@rambler.ru
D. V Petukhov
Vyatka State University
Email: evgeniyizmestev@rambler.ru
S. V Pestova
Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences
Email: evgeniyizmestev@rambler.ru
S. A Rubtsova
Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences
Email: evgeniyizmestev@rambler.ru
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