Cage-like amines in the synthesis and oxidation of camphor-10-sulfonic acid amides |
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Authors: | L I Kas’yan V A Pal’chikov A V Turov S A Prid’ma A V Tokar’ |
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Institution: | (1) Oles’ Gonchar Dnepropetrovsk National University, pr. Gagarina 72, Dnepropetrovsk, 49010, Ukraine;(2) Taras Shevchenko Kiev National University, Kiev, Ukraine |
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Abstract: | Reactions of bicyclo2.2.1]hept-5-en-exo- and -endo-2-ylmethanamines, exo-5,6-epoxybicyclo-2.2.1]hept-exo-2-ylmethanamine, 1-(bicyclo2.2.1]hept-2-yl)ethanamine, and 1-(1-adamantyl)ethanamine with camphor-10-sulfonyl chloride in chloroform in the presence of triethylamine gave the corresponding sulfonamides having two cage-like fragments. Stereoisomeric N-(bicyclo2.2.1]hept-5-en-2-ylmethyl)camphor-10-sulfonamides were oxidized with peroxyphthalic acid generated in situ from phthalic anhydride and 50% hydrogen peroxide. The exo stereoisomer was thus converted into the corresponding 5,6-epoxy derivative, while the endo isomer gave rise to 4-(7,7-dimethyl-2-oxobicyclo2.2.1]hept-1-ylmethyl)-4-azatricyclo4.2.1.03,7]-nonan-exo-2-ol (substituted azabrendane). The structure of the synthesized camphor-10-sulfonamides was confirmed by IR and 1H and 13C NMR spectra with the use of homo- (COSY) and heteronuclear 1H-13C correlation techniques (HMQC, HMBC). Heterocyclization of sulfonamides of the norbornene series was also simulated by quantum-chemical calculations at the PM3 and BHandHLYP/6-31G(d) levels of theory. |
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