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Synthesis of indole-containing analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines |
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| Authors: | V. A. Glushkov V. I. Karmanov Yu. V. Shklyaev |
| Affiliation: | (1) Siberian Branch of the Russian Academy of Sciences, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 prosp. Akad. Lavrent"eva, 630090 Novosibirsk, Russian Federation;(2) Department of Natural Sciences, Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation |
| Abstract: | The indolic analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines were obtained by Fischer indole synthesis using the acetonylcyclopropanes derived from (+)-car-3-ene. The cyano- and N-cyanamido groups in the starting carbonyl compounds did not hinder indolization. The reduction of the nitrile group bound to the asymmetrical atom of the cyclopropane ring by LiAlH4 in ether can be accompanied by epimerization or racemization. |
| Keywords: | (+)-car-3-ene cyclopropane methyl ketones Fischer indole synthesis N-cyanamides decyanation nitriles hydrolysis reduction amides indolic analogs of chrysanthemylamine epimerization racemization |
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