Aim and Objective: A new approach to synthesis of isoindoles condensed with other heterocycles and revelation of their spatial structure for biochemistry purposes was the main objective of this research.

Material and Method: Starting materials for the proposed method, 1-furyl substituted pyrrolo[1,2-a] pyrazines, pyrrolo[1,2-a][1,4] diazepines and their benzoannulated analogues - 4-furyl substituted pyrrolo[1,2-a] quinoxalines and pyrrolo[1,2-a][1,4] benzodiazepines, were synthesized by known procedures. These compounds, all containing a furfurylamine moiety, were introduced into the tandem acylation/intramolecular furan Diels-Alder (IMDAF) reaction with alpha,beta-unsaturated acid anhydrides (maleic and citraconic anhydrides). In most cases, the key step - the IMDAF reaction -proceeds diastereospecifically with simultaneous formation of five new stereogenic centers and affording the title compounds in mild conditions with satisfactory overall yields.

Results: Consequently a broad series of 10,12a-epoxypyrrolo[2', 1': 3,4] pyrazino[2,1-a] isoindoles, 11,13a-epoxy-pyrrolo[ 2', 1': 3,4][1,4] diazepino[2,1-a] isoindoles, tetrahydro-14bH-12,14a-epoxyisoindolo[2,1-a] pyrrolo[2,1-c] qui-noxalines, and tetrahydro-9H, 15bH-13,15a-epoxyisoindolo[1,2-c] pyrrolo[1,2-a][1,4] benzodiazepines was synthesized and their space structure was elucidated by X-ray analysis.

Conclusion: New effective method for synthesis of isoindoles condensed with various heterocycles was proposed. The method is based on the IMDAF reaction and provided a broad diversity of target molecules with controlled stereochemistry.