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Synthese von 3-(2-Carboxy-4-Pyridyl)- und 3-(6-Carboxy-3-pyridyl)-DL-alanin

✍ Scribed by Hans Hilpert


Publisher
John Wiley and Sons
Year
1987
Tongue
German
Weight
328 KB
Volume
70
Category
Article
ISSN
0018-019X

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✦ Synopsis


Synthesis of 3-(2-Carboxy-4-pyridyl)and 3-(6-Carboxy-3-pyridyl)-DL-alanine As starting materials for potential photochemical approaches to betalaines C (R = COOH) and to muscaflavine F (R = COOH), b-(2-carboxy-4-pyridyI)and I(-(6-carboxy-3-pyridyI)-~~-alanine (A and D with R = COOH or 4 and ll), respectively, were prepared (Scheme 1 ) . The synthesis of 4 ( = A, R = COOH) started with the 2-[(4-pyridy~)methyl]md~onate 1 and proceeded via the N-oxide 2, cyanation and hydrolysis (Scheme 2). Amino acid 11 was obtained from (3-pyridy1)methyl-bromide (6) via the malonate 7 by an analogous sequence of reactions (Scheme 3 ) .


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