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Racemic synthesis of 2′‐substituted nicotine analogs
Author(s) -
Rouchaud Anne,
Kem William R.
Publication year - 2012
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.841
Subject(s) - chemistry , alkylation , grignard reagent , reagent , nicotine , grignard reaction , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , neuroscience , biology
The chemical and pharmacological properties of 2′‐substituted nicotines are poorly understood relative to other substituted nicotines. We developed a practical synthesis of the key intermediate (±)‐2′‐cyanonicotine using the Polonovski reaction . Alkylation of (±)‐2′‐cyanonicotine with Grignard reagents led to several 2′‐alkylnicotines; (±)‐2′‐aminomethylnicotine, (±)‐2′‐hydroxymethylnicotine, and (±)‐2′‐carbamoylnicotine were also synthesized. J. Heterocyclic Chem., (2012).