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An overview of radio or stable isotope‐labeled cis ‐neonicotinoid analogs
Author(s) -
Li Chao,
Xu XiaoYong,
Liu XuanQi,
Fu QiuGuo,
Wang Wei,
Ye QingFu,
Li Zhong
Publication year - 2012
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.2949
Subject(s) - chemistry , yield (engineering) , neonicotinoid , nitromethane , pyridine , ethylenediamine , isotope , medicinal chemistry , stereochemistry , radiochemistry , organic chemistry , pesticide , materials science , physics , imidacloprid , quantum mechanics , agronomy , metallurgy , biology
To support the metabolism and toxicology study of cis ‐neonicotinoids, radio or stable isotope was introduced into different sites of the key intermediate 2‐chloro‐5‐((2‐(nitromethylene)imidazolidin‐1‐yl)methyl)pyridine (6‐Cl‐PMNI). [ 3 H 2 ]‐ and [ 14 C]‐label were successively prepared from initial materials NaB 3 H 4 and [ 14 C]‐nitromethane, respectively. Similarly, [D 2 ]‐6‐Cl‐PMNI was prepared from NaBD 4 in four steps, with 52.6% overall isotopic yield, and dual‐labeled [D 2 , 13 C]‐target was obtained from NaBD 4 and [ 13 C]‐nitromethane, affording overall isotopic yield of 42.5%. Moreover, [ 14 C 2 ] was introduced from [U‐ 14 C]‐ethylenediamine dihydrochloride in three steps, with a 58.3% overall chemical yield. Finally, typical labeled cis ‐neonicotinoids paichongding and cycloxaprid were prepared and characterized. The methods were proved to have good generality in the synthesis of other cis ‐neonicotinoids, and all results would be useful in metabolism studies of new cis ‐neonicotinoids. Copyright © 2012 John Wiley & Sons, Ltd.