Cyclocondensation of lower aliphatic aldehydes with arylamines and cyclopentadiene

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

doi:10.1007/s11172-013-0344-2

Cited by 4 publications

(4 citation statements)

References 13 publications

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“…In the case of formaldehyde 712, fused julolidine derivatives 713, arising from a double Povarov reaction, were obtained as the major product in excellent yield (Scheme 180). 318 However, ortho-substituted anilines gave only the intermediate tricyclic product arising from the first cycloaddition.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Progress in the Chemistry of Tetrahydroquinolines

2019

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Section: Chemical Reviewsmentioning

confidence: 99%

Progress in the Chemistry of Tetrahydroquinolines

2019

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“…In 1988, Grieco and Bahsas,196 in an attempt to synthesize azanorbornenes through the three-component Povarov reaction between anilines 2, formaldehyde (87) and cyclopentadiene (86) in the presence of TFA, obtained julolidines 88 as the products in yields of 84-98% (Scheme 21, A). Similarly, in 2013, Tolstikov et al 197 obtained julolidines 88 in yields of 85-92% (Scheme 21, B).…”

Section: Julolidinesmentioning

confidence: 82%

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

et al. 2022

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Multicomponent Povarov reaction is a powerful approach for the construction of N-heterocyclic containing substances. By using Povarov reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines in a single step, it is possible to form, respectively, two new Csp3-Csp3 and one Csp3-Nsp3 bonds, two new Csp2-Csp2 and one Csp2-Nsp2 bonds and four Csp3-Csp3 and two Csp3-Nsp1 bonds. This review article reports the main features of the Povarov reaction such as its mechanism, the scope of such reaction concerning to different catalysts and substrates used on it as well as the stereoselective versions of Povarov reaction

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“…5a,7 The threecomponent reaction of formaldehyde, cyclopenta-1,3-diene, and aniline or its para-substituted derivatives gave high yields of the corresponding benzodicyclopentaquinolizines with an antiplanar arrangement of the cyclopentene rings. 8 We found that the reaction of benzene-1,4-diamine (1) with formaldehyde and cyclopenta-1,3-diene in aceto-nitrile gave the nonacyclic compound 5 containing four mutually antiplanar cyclopentene moieties (Scheme 3).…”

Section: Syn Thesismentioning

confidence: 99%

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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Cyclocondensation of lower aliphatic aldehydes with arylamines and cyclopentadiene

Cited by 4 publications

References 13 publications

Progress in the Chemistry of Tetrahydroquinolines

Progress in the Chemistry of Tetrahydroquinolines

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

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

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