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 α,β-unsaturated acid anhydrides (maleic and itraconic 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-epoxypyrrolo[
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