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Total synthesis of 13 C 2 , 15 N‐imidacloprid with three stable isotopes in the pyridine ring
Author(s) -
Belov Vladimir,
Käfferlein Heiko U.
Publication year - 2019
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.3703
Subject(s) - chemistry , pyridine , imidacloprid , yield (engineering) , ring (chemistry) , isotope , residue (chemistry) , radiochemistry , stable isotope ratio , medicinal chemistry , nuclear chemistry , stereochemistry , organic chemistry , pesticide , agronomy , materials science , physics , metallurgy , biology , quantum mechanics
Imidacloprid (IC) is an important crop‐protecting insecticide worldwide and commonly used for seed treatment. However, only few data are available on human toxicity of IC. Having in view the metabolic studies at low doses in humans and residue analysis of IC in food and consumer products, we elaborated the synthesis and prepared 13 C 2 , 15 N‐IC with three stable isotopes of the “heavy” atoms in positions 1, 2, and 3 of the pyridine ring. By using readily available and affordable starting materials, 15 NH 4 Cl and 13 C 4 ‐acetic anhydride, the target compound has been prepared in eight steps with an overall yield of 13%.