Annelation of drotaverine by p-quinones to form hydroxyindolo- and hydroxybenzindoloisoquinoline derivatives |
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Authors: | L. Yu. Ukhin T. N. Gribanova L. G. Kuz’mina |
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Affiliation: | (1) Institute of Physical and Organic Chemistry, Rostov State University, 194/2 prosp. Stachki, 344090 Rostov on Don, Russian Federation;(2) N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | 1-(3, 4-Diethoxybenzyl)-6, 7-diethoxy-3, 4-dihydroisoquinoline (drotaverine, 1a) reacts with p-benzoquinone (2) and p-naphthoquinone (3) in nitromethane or during fusion to give 5-(3, 4-diethoxyphenyl)-7, 8-diethoxy-3-hydroxy-5a, 10, 11, 12-tetrahydroindolo[2, 1-a]isoquinoline (4) and 7-(3, 4-diethoxyphenyl)-9, 10-diethoxy-5-hydroxy-7a, 12, 13, 14-tetrahydrobenz[g]indolo[2, 1-a]isoquinoline (5), respectively. Compounds 4 and 5 are smoothly alkylated at the oxygen atom in the presence of bases. The structure of one alkylation product, viz., 3-allyloxy-5-(3, 4-diethoxyphenyl)-7, 8-diethoxy-5a, 10, 11, 12-tetrahydroindolo[2, 1-a]isoquinoline, was established by X-ray diffraction analysis.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 761–769, March, 2005. |
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Keywords: | drotaverine p-quinones Nenitzescu reaction indolotetrahydroisoquinoline derivatives alkylation X-ray diffraction analysis |
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