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

Preparation of 7-Methylenepyrrolo[1,2-c]pyrimidin-1(5H)-ones and their 1,3-Dipolar Cycloadditions towards Isoxazolinyl and Isoxazolidinyl Spironucleosides

R. Fischer, E. Hýrošová, Ľ. Fišera, C. Hametner, and M. K. Cyrański

Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-812 37 Bratislava

E-mail: lubor.fisera@stuba.sk

Received: 5 August 2004

Abstract: Novel 6,7-dihydro-5-hydroxy-3-methoxy-7-methylenepyrrolo[1,2- c ]pyrimidin-1(5 H )-oneswere prepared from orotic acid. Their 1,3-dipolar cycloadditions with mesitonitrile oxide and methoxycarbonyl nitrone proceed with complete regioselectivity, the approach of the dipole taking place predominantly from the less sterically hindered side of the dipolarophiles. The isoxazolidinyl spironucleoside, bearing a primary hydroxyl group on methyl in C-3 position of the isoxazolidinyl ring, was prepared in three steps from the major isoxazolidine.

Full paper in Portable Document Format: 594a275.pdf

Chemical Papers 59 (4) 275–288 (2005)