Some reactions of 1,2‐dihydropyridines with cyanogen azide. Synthesis of üiazabieyclo[4.1.0]hept‐4‐enes

Ondrus, T. A.; Knaus, Edward E.; Ciam, C. S.

doi:10.1002/jhet.5570160246

Cited by 13 publications

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“…Polysubstituted 1,2-dihydropyridines have been found to undergo [4+2] cycloaddition as reactive dienes with maleic anhydride, dimethyl fumarate and methyl acrylate, leading to the formation of 2-azabicyclo[2.2.2]oct-7-enes [ 34 ]. The regiospecific 1,3-dipolar cycloaddition reaction of 1,2-dihydropyridines with cyanogen azide and per(poly)fluoroalkanesulfonyl azides has afforded corresponding 2,7-diazabicyclo[4.1.0]hept-4-enes and N -(1,2,3,6-tetrahydropyridylidene)fluoroalkanesulfonylamides [ 35 , 36 ]. The alkylation and acylation reactions of 2-alkyl(phenyl)-1-lithio-1,2-dihydropyridines has also been investigated [ 37 , 38 , 39 , 40 ].…”

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confidence: 99%

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

et al. 2020

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New fluorinated 3,6-dihydropyridines were obtained by the electrophilic fluorination of 1,2-dihydropyridines with Selectfluor®. These 3-fluoro-3,6-dihydropyridines were easily converted to corresponding pyridines by the elimination of hydrogen fluoride under mild conditions. A new approach to the synthesis of methyl 2-(fluoromethyl)-5-nitro-6-arylnicotinates by the fluorination of 3-fluoro-2-methyl-5-nitro-3,6-dihydropyridines or 1,2-dihydropyridines with Selectfluor® has been developed.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

et al. 2020

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Cyanogen Azide

Goldsmith¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Small and Medium Rings, 79¹⁾ 4‐Azatetracyclo[3.3.0.0^2,8.0^3,6]octanes: New Hetereocycles by Addition of Sulfonyl Azides to 7‐Substituted Norbornadienes – Experimental Verification of σ Interactions in the Norbornane Skeleton

et al. 1991

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The reaction of six ?-substituted norbornadienes with seven sulfonyl azides has been investigated. The products consist of either the novel azatetracyclic system 1 or the stereoisomeric bicycles 2 or of a mixture of them. The chemical behaviour of 1 has been studied. Mechanistically the results may be rationalized within the frame of the Mazzocchi-Houk model. The theoretical predictions of this model, concerning the K* and cr* energies, were confirmed experimentally by using electron-transmission spectroscopy.1,3-Dipolar cycloadditions to 7-substituted norbornadienes do not exclusively follow Alder's exo rule2), but show a complex stereochemical behaviour with regard to their exo/endo and synlanti stereosclectivity. Thus, for the addition of phenyl azide to 7-tertbutoxynorbornadiene Klumpp et al. 3, found 55% syn-endo, 30% anti-exo, and even 15% of the sterically demanding syn-exo adduct.Contrary to this, Fran~k-Neumann~), Wilt 'I, and co-workers reported on a stereoselcctive endo-anti cycloaddition of diazoalkanes to 7-chloronorbornadiene. However, such a stereoselectivity was not found for 7-oxygenated norbornadienes.Kinetic studies on cycloadditions of hexachlorocyclopentadiene6.'' showed that the reactivity decreases with increasing electronegativity of the substituent in the 7-position and that the exoanti attack is strongly inhibited. These findings were confirmed by recent investigations performed by De Micheli, Gandolfi, and Houk concerning the addition of mesitylenecarbonitrile oxide to 7-substituted norbornadienes.The addition of sulfonyl azides to norbornadienes is particularly intercsting since the resulting unstable triazolines undergo remarkable rearrangement reactions. Thus, Franz and Osuch') found that the addition of phenylsulfonyl azide to 7-substituted norbornadienes afforded the azabicycles 2 in 68% yield besides an isomeric sideproduct which displayed only signals of aliphatic hydrogen atoms in its 'H-NMR spectrum and for which one of the two tetracyclic structures 1 or 3 was assumed, Scheme 1

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Some reactions of 1,2‐dihydropyridines with cyanogen azide. Synthesis of üiazabieyclo[4.1.0]hept‐4‐enes

Cited by 13 publications

References 5 publications

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

Cyanogen Azide

Small and Medium Rings, 79¹⁾ 4‐Azatetracyclo[3.3.0.0^2,8.0^3,6]octanes: New Hetereocycles by Addition of Sulfonyl Azides to 7‐Substituted Norbornadienes – Experimental Verification of σ Interactions in the Norbornane Skeleton

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Some reactions of 1,2‐dihydropyridines with cyanogen azide. Synthesis of üiazabieyclo[4.1.0]hept‐4‐enes

Cited by 13 publications

References 5 publications

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

Cyanogen Azide

Small and Medium Rings, 791) 4‐Azatetracyclo[3.3.0.02,8.03,6]octanes: New Hetereocycles by Addition of Sulfonyl Azides to 7‐Substituted Norbornadienes – Experimental Verification of σ Interactions in the Norbornane Skeleton

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Small and Medium Rings, 79¹⁾ 4‐Azatetracyclo[3.3.0.0^2,8.0^3,6]octanes: New Hetereocycles by Addition of Sulfonyl Azides to 7‐Substituted Norbornadienes – Experimental Verification of σ Interactions in the Norbornane Skeleton