Abstract
3-(N-phenylcarboxamido)-coumarin 1 reacted with chlorosulfonic acid to give the corresponding sulfaniyl chloride 2 . However, isonicotinic acid anilide 14 , and nicotinic acid anilide 33 , reacted with chlorosulfonic acid in a 1:6 molar ratio, only for conversion into sulfanilyl chlorides 15 and 34 . Treatment with nucleophilic reagents afforded amino acid derivatives 3–6 , 16–20 , and 35–37 . Some of the corresponding methyl esters 7–9 , 21 , 24 , and 38–39 were prepared. Hydrazinolysis of some methyl esters yielded hydrazides 25–28 and 40–41 . Coupling reactions of some amino acid derivatives with amino acid methyl ester hydrochloride in THF-Et 3 N medium using the dicyclohexyl carbodiimide DCC furnished the desired dipeptide methyl esters 10–13 , 29–32 , and 42–43 . The spectral properties of the compounds are briefly discussed.
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