An important way of forming the indole cycle is the Nenitsescu reaction. Convenient precursors for this reaction are readily available β-ketoesters or 1,3-diketones, which after conversion to enamines react with 1,4-quinones to form polysubstituted indoles. The regio- and chemoselectivity of the interaction depends on the conduction conditions, the structure of the quinone and enamine component, and the electronic effects of the substituents. Studies have shown that the condensation of quinones with enamines can take place in at least a few main directions. The most common are 5- or 6-hydroxyindoles, 5-hydroxybenzofurans and 5-hydroxyindazoles. However, the synthetic potential of the reaction is not limited to this, because it also allows to obtain other, more diverse structures that are difficult to access in other ways – benzocarbazoles, pyrido- [2,3- b ]indoles, furo[3,2- h ]indoles, furo[2,3- g ]indoles, imidazo[4,5- g ]indoles, dihydro-benzo[ g ]indoles, pyrrolo[2,3- h ]quinolines. However, interest in this reaction has not diminished to this day, as it is a convenient method of forming a base fragment for many biologically active substances. In this paper, we describe the results of studies obtained during the study of the reactivity of monoarylquinones to enamines derived from cyclic ketones and secondary amines. With the use of such enamines, it is impossible to obtain indoles by the Nenitsescu reaction, so the formation of benzofuran derivatives was expected, but the question of regioselectivity of the process remained open. It was found that the interaction of 1-morpholino-1-cyclohexene 6 with 2-aryl-1,4-benzoquinones 1 – 5 at room temperature in a dry benzene forms 4-aryl-5a-morpholin-4-yl-5a,6,7,8,9,9a-hexahydrodibenzo[ b , d ]furan-2-oles 7 – 11 . The reaction was found to be regioselective – of the three possible regioisomers, only 4-aryl-substituted dibenzofurans were formed, and no indole cyclization products were detected. The structures of the synthesized compounds were confirmed by the 1 H-, 13 C NMR spectroscopy and element analysis data. Keywords: 2-aryl-1,4-benzoquinones, 1-morpholino-1-cyclohexen, enamines, Nenitzescu reaction, dibenzo[ b , d ]furan-2-ones, heterocycles.