The water-base cleavage reaction of 2,2-dialkyl-4-hydroxymethylbenz[f]isoindolinium bromides and chlorides (2b-g) and (4a-g) was investigated. It was established that the above-mentioned salts in water-base cleavage reaction undergo intramolecular recyclization. As a result 1,3-dihydro-4-dialkylaminomethylnaphto[1,2-c]furans (5a-g) are obtained in 62-72% yields. The same products in 65-70% yields may be obtained by step cyclization cleavage reaction of dialkyl-4-hydroxybutyn-2-yl-(3-phenylpropargyl) ammonium salts (1b-g) and (3a-g), as well. The structure of the resulting amines 5a-g are determined and approved by X-ray diffraction, nmr and ir spectroscopic methods.

A New Intramolecular Recyclization in Water-Base Cleavage Reaction of 2,2-Dialkyl-4-hydroxymethylbenz[f]isoindolinium Bromides and Chlorides. -(CHUKHAJIAN, E. O.; GEVORKYAN, H. R.; CHUKHAJIAN, E. O.; SHAHKHATUNI, K. G.; PANOSYAN, H. A.; TAMAZYAN, R. A.; J. Heterocycl.

It was found that dialkyl(4-hydroxybut-2-ynyl)methallyl-and dialkylcrotyl(4-hydroxybut-2-ynyl)-ammonium halides undergo a Stevens rearrangement under the influence of aqueous alkali with transfer of the reaction center in the receiving group and inversion of the migrating group followed by cyclization to amino derivatives of furan. bromides, intramolecular cyclization, aqueous-alkali cleavage, Stevens rearrangement.During the action of twice the molar amount of sodium hydroxide with heat in aqueous solution, dialkylallyl(4-hydroxybut-2-ynyl)ammonium bromides undergo a Stevens rearrangement with transfer of the reaction center and form amino alcohols containing an allene group, the intramolecular cyclization of which leads to N,N-dialkyl-4-allyl-2,5-dihydrofuran-2-ylamines [1].In order to investigate the universality of the rearrangement-cyclization reaction and the production of new amines with a pharmacophoric hydrogenated furan ring in the present work we studied the behavior of dialkyl(4-hydroxybut-2-ynyl)methallylammonium chlorides 1a-f and dibutylcrotyl(4-hydroxybut-2-ynyl)-ammonium (2a) and N-crotyl-N-(4-hydroxybut-2-ynyl)mopholinium (2b) bromides toward aqueous alkali (Table 1).It was established that the salts 1a-f and 2a,b also undergo rearrangement-cyclization when heated for 2 h at 90-92°C with twice the molar amount of sodium hydroxide and form the corresponding 2-diethylamino-

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