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Selenium‐sulfur analogs. 4. Synthesis and characterization of (±)‐β‐(2‐amino‐1,3‐selenazol‐4‐yl)alanine
Author(s) -
Hanson Robert N.,
Davis Michael A.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180141
Subject(s) - chemistry , protonation , alanine , thiazole , amino acid , sulfur , stereochemistry , selenium , proton nmr , organic chemistry , biochemistry , ion
The novel amino acid (±)‐β‐(2‐amino‐1,3‐selenazol‐4‐yl)alanine 4a was prepared from selenourea and 1,3‐dichloropropan‐2‐one via a four‐step synthetic sequence. Nuclear magnetic resonance analysis indicated a downfield chemical shift of δ 0.29 to 0.30 and δ 0.57 for the C 5 ‐proton of the protonated 2‐amino‐and 2‐acetamido‐1,3‐selenazoles respectively compared with the analogous thiazoles. The infrared spectra of the selenazole and corresponding thiazole compounds were virtually identical.