Improved preparation of racemic 2-amino-3-(heteroaryl)propanoic acids and related compounds containing a furan or thiophene nucleus |
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Authors: | Kitagawa Tokujiro Khandmaa Dashrenchin Fukumoto Ayumi Asada Makoto |
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Affiliation: | Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Nishi-ku, Kobe 651-2180, Japan. kitagawa@pharm.kobegakuin.ac.jp |
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Abstract: | Racemic 2-amino-3-(heteroaryl)propanoic acids (1), mostly with a furan or thiophene nucleus as a heteroaryl group, were synthesized in 48-94% yield by the reduction of 3-(heteroaryl)-2-(hydroxyimino)propanoic acids (5) with zinc dust and formic acid in the presence of a catalytic amount of iron dust at 60 degrees C for 2 h. Under these conditions, unfavorable hydrogenolysis of bromine on the thiophene nucleus does not occur. Traditional N-formylation of the prepared 3-(heteroaryl)alanine (1) with a mixture of formic acid and acetic anhydride afforded 2-(formylamino)-3-(heteroaryl)propanoic acids (6) in 51-95% yield. |
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