Synthesis of some n-substituted derivatives of 1-(1h-pyrrole-1 -ylmethyl)- 10-oxa-4-azatricyclo [5.2.1.0(2,6)]dec-8-ene-3,5-dione with an expected anxiolytic activity.

gepirone, ipsapirone, tandospirone and others) are 1arylpiperazine derivatives with a high affinity to the 5HT1A receptor (1-3). Therefore, they are widely used in the treatment of psychotic and neurotic disorders. This paper is a continuation of our research in the field of 4aryl/heteroaryl piperazinylalkyl derivatives (4, 5) of 1(1H-pyrrole-1-ylmethyl)-10-oxa-azatricyclo[5.2.1.0] dec-8-ene-3,5-dione. Here we describe the synthesis of a series of isoindole-modified analogs related to tandospirone (Figure 1). Our starting material was isoindole I (Scheme 1), obtained in the Diels-Alder reaction of 1-(2furylmethyl)-1H-pyrrole with maleimide. By alkylation of the imide I with 1,4-dibromobutane, respectively, N4-bromobutyl substituted derivative II was obtained. Next, compound II was condensed with appropriate amines to give derivatives III ñ X. The structures of compounds I-X have been established on the basis of H NMR spectra and elemental analysis.