SYNTHESIS AND STRUCTURE OF 2-METHYL-6-OXO-7,8-DIHYDROSPIRO(BENZO[<i>h</i>]TRIAZOLO[3,4-<i>b</i>]QUINAZOLINE-7,1'-CYCLOPENTANE)

Abstract

The reaction of 4-amino-3-ethoxycarbonyl-1,2-dihydrospiro(naphthalene-2,1'-cyclopentane) with benzoyl isothiocyanate led to the corresponding 4-(N'-benzoylthioureido) derivative, the cyclization of which gave 4-oxo-2-thioxo-1,2,3,4,5,6-hexahydrospiro(benzo[h]quinazoline-5,1'-cyclopentane). Condensation of the latter with hydrazine hydrate gave 2-hydrazino-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1'-cyclopentane), which formed 6-oxo-1H-7,8-dihydrospiro(benzo[h]triazolo[3,4-b]quinazoline-7,1'-cyclopentane) in reaction with orthoformic ester. Methylation of the product with methyl iodide led to its 2-methyl derivative.

Authors: A. I. Markosyan, R. A. Kuroyan, S. V. Dilanyan, M. S. Aleksanyan, A. A. Karapetyan, and Yu. T. Struchkov.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (5), pp 574-578

http://link.springer.com/article/10.1007/BF02290848