Racemic synthesis of 2′-substituted nicotine analogs

✍ Scribed by Anne Rouchaud; William R. Kem

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2011
• Tongue: English
• Weight: 126 KB
• Volume: 49
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.841

✦ Synopsis

Abstract

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).