Quinoline derivatives R 0410Product Structure in the Reaction of Dimethyl Acetylenedicarboxylate with 2-Furyl-1,2,3,4-tetrahydroquinolines. -(ZUBKOV, F. I.; ZAITSEV, V. P.; ORLOVA, A. A.; PEREGUDOV, A. S.; MIKHAILOVA, N. M.; VARLAMOV, A. V.; Russ.
Intramolecular cycloaddition of alkenes to nitrons is an efficient method of constructing hinged bridge systems [1][2][3][4]. Due to the high regio-and stereospecificity of formation of adducts and ease of transformation of their isoxazolidine fragment, this reaction was used in synthesis of complex structures, for example, the alkaloid luciduline [5], prostaglandins [6], secoishvaranol-12 sesquiterpene [3], and ambrosin [7].Synthesis of 2-phenyi-1-aza-7-oxabicyclo[2.2.1 ]heptane by thermal cyclization of N-benzylidene-3-butenamine N-oxide was described for the first time in [1]. Bicycloheptane was transformed into c/s-l-methyl-2-phenylpiperidin-4-ol by successive hydrogenolysis and N-methylation. It was later found [2] that thermal cyclization of N-benzylidene(undecylidene)(3-trimethylsilyl-4-pepten-2-yl)amines results in the formation of a mixture of isomeric (with respect to the position of the substituents) 1-aza-7-oxabicyclo[2.2.1]heptanes, whose hydrogenolysis yielded a mixture of isomeric (with respect to the position of the substituents) piperidin-4-ols.We used the strategy of the researchers in [1] to construct 2e-phenyl-4e-hydroxy-l-aTaspiro[5.5]undecane --the spiro(piperidine-2-cyclohexane) system on which the alkaloids histrionicotoxin and perhydrohistrionicotoxin are based [8, 9].
3,9 ]undec-3-ene-6,1'-cyclohexane]. -(NIKITINA, E. V.; SAFRONOVA, A. A.; VARLAMOV, A. V.; ZUBKOV, F. I.; ALEKSANDROV, G. G.; TURCHIN, K. F.; Chem. Heterocycl. Compd. (N. Y.) 39 (2003) 1, 130-131; Russ. Peoples' Friendship Univ., Moscow 117198, Russia; Eng.) -Staver 37-135
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