Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Note | Regular issue | Vol 81, No. 2, 2010, pp.413-420
Published online, 1st December, 2009
DOI: 10.3987/COM-09-11859
S-Methylation of N-Containing Heterocyclic Thiols with Conjugated Acids of Methoxy Groups

Masao Shimizu,* Teruaki Shimazaki, Yoshihiro Kon, and Takeo Konakahara

*Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 Tsukuba, Japan

Abstract

2-Mercaptopyridine-3-carboxylic acid reacts with methanol under acidic conditions to afford the corresponding S-methylated methyl ester, methyl 2-methylthiopyridine-2-carboxylate. Such S-methylation occurred for various N-containing heterocyclic thiols with acidic methanol. The reaction proceeded by the attack of mercapto groups on the conjugated acid of methanol. Therefore, the sulfur atom of pyridine-2-thiol was also methylated with acidic methyl ethers or methyl esters.