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The reaction of 2‐ethoxycarbonyl‐3‐isothiocyanatopyridine with α‐amino acids. The synthesis of 3‐substituted 2‐thiooxo‐2,3‐dihydropyrido[3,2‐ d ]pyrimidin‐4(3 H )‐ones
Author(s) -
Urleb UroŠ,
Stanovnik Branko,
Tišler Miha
Publication year - 1990
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.5570270257
Subject(s) - chemistry , racemization , pyrimidine , hydrazide , hydrazine (antidepressant) , ring (chemistry) , amino acid , alanine , medicinal chemistry , stereochemistry , organic chemistry , chromatography , biochemistry
2‐Ethoxycarbonyl‐3‐isothiocyanatopyridine ( 1 ) reacts with α‐amino acids 2–11 and β‐alanine ( 12 ) to give pyrido[3,2‐ d ]pyrimidine derivatives 13–23 with the nitrogen of the amino acid component being incorporated into the fused pyrimidine ring at position 3 . Methylation of 14 and 15 with DMFDMA produces S ‐methylated products 24 and 25 , while in the reaction of 14 with hydrazine the corresponding hydrazide 26 is formed. The reactions proceed under mild conditions, so that no racemization of chiral substituents was observed.