Solid-phase synthesis of pyrazolopyridines from polymer-bound alkyne and azomethine imines

Kirsi Harju; Irene Kylänlahti; Timo Paananen; Mika Polamo; John Nielsen; Jari Yli-Kauhaluoma

doi:10.1021/cc050138j

Solid-phase synthesis of pyrazolopyridines from polymer-bound alkyne and azomethine imines

J Comb Chem. 2006 May-Jun;8(3):344-9. doi: 10.1021/cc050138j.

Authors

Kirsi Harju¹, Irene Kylänlahti, Timo Paananen, Mika Polamo, John Nielsen, Jari Yli-Kauhaluoma

Affiliation

¹ Division of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Helsinki, Finland.

PMID: 16677003
DOI: 10.1021/cc050138j

Abstract

Study was made of the 1,3-dipolar cycloaddition of polymer-bound alkynes to azomethine imines generated in situ from N-aminopyridine iodides. Aromatization of the cycloadducts gives polymer-bound pyrazolopyridines that can be released from the resin as carboxylic acids with trifluoroacetic acid or as methyl esters with sodium methoxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Azo Compounds / chemistry*
Imines / chemistry*
Methanol / chemistry
Models, Chemical
Polymers / chemistry
Pyrazoles / chemical synthesis*
Pyrazoles / pharmacology
Pyridines / chemical synthesis*
Pyridines / pharmacology
Technology, Pharmaceutical

Substances

Alkynes
Azo Compounds
Imines
Polymers
Pyrazoles
Pyridines
azomethane
Methanol