Issue 25, 2012
From the journal:

Organic & Biomolecular Chemistry

Imidazo[1,5-a]pyridine-1-ylalkylalcohols: synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures†

Toshiaki Murai,*a   Eri Nagaya,a   Fumitoshi Shibaharaa  and  Toshifumi Maruyamaa  

* Corresponding authors

a Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
E-mail: mtoshi@gifu-u.ac.jp
Web: http://www1.gifu-u.ac.jp/~murai_ap/murai_lab/Welcome.html
Tel: +(81)58-293-2614

Abstract

Iodine-mediated cyclization of N-thioacyl 1,2-aminoalcohols derived from aromatic aldehydes and ketones mainly produced bis(1-imidazo[1,5-a]pyridyl)arylmethanes, whereas the reaction of N-thioacyl 1,2-aminoalcohols derived from aliphatic aldehydes and N-thioacyl 1,2-aminoalcohols protected with a silyl group with iodine gave imidazo[1,5-a]pyridine-1-ylalkylalcohols as a major product.

Graphical abstract: Imidazo[1,5-a]pyridine-1-ylalkylalcohols: synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures

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Article information

DOI
https://doi.org/10.1039/C2OB25438G
Article type
Paper
Submitted
29 Feb 2012
Accepted
19 Apr 2012
First published
21 May 2012

Org. Biomol. Chem., 2012,10, 4943-4953

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Imidazo[1,5-a]pyridine-1-ylalkylalcohols: synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures

T. Murai, E. Nagaya, F. Shibahara and T. Maruyama, Org. Biomol. Chem., 2012, 10, 4943 DOI: 10.1039/C2OB25438G

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