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Reactivity of heminale azine – 5',6',7',8'-tetrahydro-1′Н-spiro[cyclohexane-1,2'-quinazoline]-4'(3'Н)-one and its derivatives
Authors: V.I. Markov, O.K. Farat, S.A. Varenichenko, E.V. Zaliznya, Yu.P. Stroev
Number of views: 402
This review contains data on the reactivity of heminal azine − 5',6',7',8'-tetrahydro-1'H spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one and the chemical properties of his rearrangements products. The main results of the investigations are presented which have been performed at the TOSPhP department of Ukrainian State University of Chemical Technology during last five years. We have studied in detail the Mannich aminoalkylation of this compound with primary amines which leads to the formation of a heterocyclic system containing an annelated azabicyclic fragments. The hydrolysis of the indicated spirans gives 3-azabicyclo[3.3.1]nonanes. These compounds show a variety of biological activity (for instance, analgetic and antimicrobial one). Hence, the development of new methods for preparing novel polycyclic 3-azabicyclo[3.3.1]nonanes is an actual goal. We investigated the formylation of 5',6',7',8'-tetrahydro-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one and discovered a new multistage domino reaction which enables to obtain tricyclic acridine systems due to the deep rearrangement of the carbon skeleton. In the present work we showed that the rearrangement of 5',6',7',8'-tetrahydro-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one and its analogues under Vilsmeier-Haack conditions is of a general nature. The reaction is sensitive to increased temperatures and in the case of some derivatives it is nonselective and gives a hardly separable mixture of resinous products. It is proposed to consider the rearrangements of azine, which are based on pyrimidine-to-pyridine transformation induced electrophile attack, as an AERORC-process.