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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 2, Number 4
April 20, 1981 

Synthesis of Nucleophilic Adducts of Thiols (Ⅰ). Addition of Cysteine to β-Nitrostyrene Derivatives
Tae-Rin Kim, Sung-Young Choi
The addition reactions of cysteine without blocking amino and carboxyl groups to substituted and unsubstituted β-nitro-styrene derivatives were investigated. β-Nitrostyrene(1a), p-methyl-β-nitrostyrene(1b), 3,4,5-trimethoxy-β -nitrostyrene(1c), ω-3,4-methylenedioxy-β -nitrostyrene(1d), o-, m- and p-chloro-β -nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-β-nitrostyrene (1h, 1i, 1j) easily undergo addition reactions with cysteine to form S-(2-nitro-1-phenylethyl)-L-cysteine(3a), S-[2-nitro-1-(p-methyl)phenylethyl]-L-cysteine(3b) , S-[2-nitro-1-(3',4',5'-trimethoxy)phenylethyl]-L-c ysteine(3c), S-[2-nitro-1-(ω -3',4'-methylenedioxy)phenylethyl]-L-cysteine(3d), S-[2-nitro-1-(o-chloro)phenylethyl]-L-cysteine(3e) , S-[2-nitro-1-(m-chloro)-phenylethyl]-L-cysteine(3f ), S-[2-nitro-1-(p-chloro)phenylethyl]-L-cysteine(3g) , S-[2-nitro-1-(o-methoxy)phenylethyl]-L-cysteine(3 h), S-[2-nitro-1-(m-methoxy)phenylethyl]-L-cysteine(3 i) and S-[2-nitro-1-(p-methoxy)phenylethyl]-L-cysteine(3j ), respectively. The structure of adducts were confirmed by means of UV-spectrum, IR-spectrum, molecular weight measurement and elemental analysis. The various factors effecting the yield of cysteine adducts to β-nitrostyrene derivatives were also studied.
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