N-Trifluoroacetyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline ozonides

Толстиков, А. Г.; Савченко, Р. Г.; Nedopekin, D. V.; Афонькина, С. Р.; Lukina, E. S.; Odinokov, V. N.

doi:10.1007/s11172-011-0024-z

Cited by 7 publications

(7 citation statements)

References 24 publications

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“…The coupling constant (9 Hz) of the vicinal protons at the stereogenic carbon centers confirms their cis-orientation. A single-crystal X-ray structure determination of 4a ( Figure 2) confirmed the NMR assignments and established that 4a has the structure (3aS*,4R*,6bS*,9aS*,10R*,12bS*)-4,10bis(2-fluorophenyl)-3,3a,4,5,6b,9,9a,10,11,12b-decahydro-cyclopenta[c]cyclopenta [4,5]pyrido [2,3-g]quinoline.…”

Section: Syn Thesismentioning

confidence: 59%

“…The octahydropyridoquinoline core is relatively flat, and the cyclopentene moieties are coplanar and syn-oriented relative to the molecular plane ( Figure 1). The symmetrically arranged stereogenic carbon atoms in positions 3a and 9a, 4 and 10, and 6b and 12b have the corresponding pairwise-identical S*, R*, and S* relative configurations, respectively, and the structure (3aS*,4R*,6bS*,9aS*,10R*,12bS*)-4,10-bis(2-fluorophenyl)-3,3а,4,5,6b,9,9a,10,11,12b-decahydrocyclopenta[c]cyclopenta [4,5]pyrido[2,3-g]quinoline can be assigned to compound 3a.…”

Section: Syn Thesismentioning

confidence: 99%

“…(3аR*,3dR*,6aS*,9aS*,12aR*,12dR*,15aS*,18aS*)-1,3a,3d,6, 6a,7,9,9a,10,12a,12d,15,15a,16,18,18a-hexadecahydrodicyclopenta[a,k]biscyclopenta [4,5]pyrido[1,2,3-de:3′,2′,1′-gh]-4,7-phenanthroline to compound 5.…”

Section: Paper Syn Thesismentioning

confidence: 99%

“…1b,3 By using this method, cyclopentene-fused tetrahydroquinolines have been synthesized from arylamines, aromatic aldehydes, and cyclopenta-1,3diene. 4 The involvement of aromatic diamines in a similar reaction provides a rapid route for the synthesis of diazaheterocycles fused to two cyclopentene moieties. Whereas the reaction of aromatic amines, aldehydes, and alkenes has been widely used, there are only a few reports on the use of isomeric benzenediamines in similar reactions.…”

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confidence: 99%

“…ORTEP drawings of (3aS*,4R*,6bS*,9aS*,10R*,12bS*)-4,10bis(2-fluorophenyl)-3,3a,4,5,6b,9,9a,10,11,12b-decahydrocyclopenta[c]cyclopenta[4,5]pyrido[2,3-g]quinoline 3a with a thermal ellipsoid plot (50% probability for nonhydrogen atoms)…”

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One-Pot Synthesis of Novel Cyclopentene-Fused Octahydropyridoquinolines and Octahydrophenanthrolines

et al. 2015

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New cyclopentene-fused octahydropyridoquinolines and octahydrophenanthrolines were prepared by a stereoselective three-component cyclocondensation of benzene-1,4-diamine, cyclopenta-1,3-diene, and an aromatic aldehyde. Single-crystal X-ray diffraction data provided evidence for the formation of cyclopentene-fused octahydropyridoquinolines and octahydrophenanthrolines with a syn-planar arrangement of the cyclopentene rings. The cyclocondensation of benzene-1,4-diamine, cyclopenta-1,3-diene, and formaldehyde gave new type of polycyclic compound containing four cyclopentene moieties oriented in a mutually antiplanar manner.The multicomponent coupling strategy is recognized as an effective and powerful approach that permits ready access to polycarbocycles and to polyheterocycles. 1 Among nitrogen heterocycles, quinolines and their derivatives are a class of organic compounds that are attracting interest from both synthetic and medicinal chemists. 2 A three-component modification of the Povarov reaction, which can also be classified as a formal [4+2] cycloaddition of an aromatic imine (Schiff base) with a nucleophilic olefin (the azaDiels-Alder reaction) is an important tool for the synthesis of quinoline derivatives. 1b,3 By using this method, cyclopentene-fused tetrahydroquinolines have been synthesized from arylamines, aromatic aldehydes, and cyclopenta-1,3-diene. 4 The involvement of aromatic diamines in a similar reaction provides a rapid route for the synthesis of diazaheterocycles fused to two cyclopentene moieties. Whereas the reaction of aromatic amines, aldehydes, and alkenes has been widely used, there are only a few reports on the use of isomeric benzenediamines in similar reactions. 5 We investigated the cyclocondensation of benzene-1,4-diamine with cyclopenta-1,3-diene and various aromatic aldehydes or formaldehyde, and we synthesized several novel octahydropyridoquinolines and octahydrophenanthrolines fused to cyclopentene moieties.Benzene-1,4-diamine (1) has two free ortho positions at each amine group, and a three-component condensation involving this substrate would be expected to give two regioisomeric bis adducts with distant and close cyclopentene moieties. The trifluoroacetic acid-catalyzed reaction of benzene-1,4-diamine 1, an aromatic aldehyde 2, and cyclopenta-1,3-diene in a 1:2:6 molar ratio in acetonitrile at room temperature for 20 minutes gave a 1:1 mixture of products 3 and 4, which were easily separated by column chromatography (Scheme 1).Note that a Povarov monoadduct (involving one of the two amine groups) was not formed, even when an equimolar amount of the aldehyde was used. It is likely that adduct formation at the second amine group occurs at a higher rate.The structures of newly prepared compounds 3a-d and 4a-d were established by using one-and two-dimensional 1 H and 13 C NMR spectroscopy, mass spectrometry, and IR spectroscopy and they were confirmed by single-crystal Xray diffraction studies on compounds 3a, 4a, and 4b.MALDI/TOF mass spectrometry showed that compound 3a [R f =...

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Section: Syn Thesismentioning

confidence: 59%

Section: Syn Thesismentioning

confidence: 99%

Section: Paper Syn Thesismentioning

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