A number of pyrrolo[2',3':4,5]furo[3,2-c]pyridines (5a-5d) were prepared by the reaction of corresponding iminophosphoranes (4a, 4b), available from substituted vinylazides (1a, 1b) and triphenylphosphine, with phenyl or 3-chlorophenyl isocyanates. The appropriate vinylazides (1a, 1b) were used for the preparation of substituted furo[3,2-b:4,5-b]dipyrroles (2a, 2b). Compounds (3a, 3b) were prepared in phase transfer catalysis conditions