Reactions of 4-oxobutanoic acids as well as their cyclic analogues 3H-furan-2-ones with 1,3-binucleophilic reagent (2-aminophenyl) methanol lead to the formation of 1-R-5H-benzo[d]pyrrolo[2,1-b][1,3]oxazines and 3a-R-2,3,3a-trihydro-5H-benzo[d]pyrrolo[2,1-b][1,3]oxazin1-ones, respectively. Quantum-chemical calculations of the Fukui reactivity indices and local hardness have substantiated the mechanisms of the reactions carried out.