Imidazopteridines. I. Synthesis of Imidazo[1,2-c]pteridine and Its Alkyl Derivatives

Autor:	Sadao Matsuura, Keiko Shibata, Takashi Sugimoto
Rok vydání:	1977
Předmět:	chemistry.chemical_classification Pyrazine Chemistry Stereochemistry General Chemistry Triethyl orthoformate Turn (biochemistry) Hydrolysis chemistry.chemical_compound Yield (chemistry) medicine Chloroacetaldehyde Alkyl Pteridine medicine.drug
Zdroj:	Bulletin of the Chemical Society of Japan. 50:2744-2747
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.50.2744
Popis:	The synthesis of imidazo[1,2-c]pteridine and its alkyl derivatives is described. The reaction of 4-aminopteridine with chloroacetaldehyde gave the ring-opened 2-formamido-3-(2-imidazolyl)pyrazine and the isomeric 2-amino-3-(1-formyl-2-imidazolyl)pyrazine but no imidazopteridine. 4-Amino-2-methylpteridine and chloroacetaldehyde similarly gave 2-acetamino-3-(2-imidazolyl)pyrazine in high yield. Hydrolysis of these compounds gave 2-amino-3-(2-imidazolyl)pyrazine, which was used as the key intermediate for the synthesis of the title compounds. Thus it reacted with triethyl orthoformate and homologues to give respectively the parent imidazo-[1,2-c]pteridine and its 6-methyl and 6-ethyl homologues. Their 2,3-dimethyl derivatives were prepared likewise from 2-amino-3-(2-imidazolyl)-5,6-dimethylpyrazine, which in turn was prepared from 4-amino-6,7-dimethyl- or 4-amino-2,6,7-trimethylpteridine.
Databáze:	OpenAIRE
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