ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and cyclization reactions with pyrazolopyrimidinyl keto esters part I. Reactivity of pyrazolopyrimidinyl β-keto ester and pyrazolopyrimidinyl α,β-unsaturated ketones

M. A. A. Awas

Department of Chemistry, Faculty of Education, Ain-Shams University, Roxy, 11711 Cairo, Egypt

E-mail: dr.mohamedawas1@hotmail.com

Received: 27 January 2006  Revised: 19 April 2006  Accepted: 25 April 2006

Abstract: 5-Acetyl-4,5-dihydro-1-phenylpyrazolo[3,4-d]pyrimidin-4-one was prepared and subjected to various chemical transformations to give novel 5-heterocyclic pyrazolopyrimidinone derivatives of expected important biological activity. Then, the latter compounds were used to obtain β-keto ester and α,β-unsaturated carbonylpyrazolopyrimidinones which were used as alternate precursors to produce new pyrazolopyrimidinones substituted with five-membered heterocycles such as pyrazole and isoxazole. The structure of these compounds was identified on the basis of their chemical behaviour as well as elemental and spectral analysis.

Keywords: pyrazolopyrimidinyl - keto esters - ketones - synthesis - cyclization - cellobiase activity

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-006-0062-4

Chemical Papers 60 (5) 338–347 (2006)