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Synthesis of 6‐substituted benzo[ a ]pyrene‐α‐ 14 C derivatives
Author(s) -
Hicks James L.,
Heys J. Richard
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580181009
Subject(s) - chemistry , pyrene , hydroxymethyl , aldehyde , benzo(a)pyrene , carboxylic acid , methylation , organic chemistry , medicinal chemistry , biochemistry , catalysis , dna
6‐Lithiobenzo[ a ]pyrene was carbonated to produce benzo[ a ]pyrene‐6‐carboxylic‐ 14 C acid, which was in turn used in the preparation of several derivatives. Methylation to the ester was followed by LiAlH 4 reduction to 6‐hydroxymethyl‐ 14 C‐benzo[ a ]pyrene. An efficient oxidation using DDQ produced the corresponding aldehyde. Direct reduction of the ester using LiAlH 4 and AlCl 3 produced 6‐methyl‐ 14 C‐benzo[ a ]‐pyrene.