Synthesis of dehydroabietane-derived sulfonamides with fragments of L-amino acid esters and hydrazides

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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.

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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