Synthesis of Heterocyclic Compounds by Cycloaddition Reactions. IV Azomethines as Dienophiles

Kasper, Franz; Dathe, S.

doi:10.1002/prac.19853270628

Cited by 9 publications

(2 citation statements)

References 7 publications

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“…Diels-Alder reactions of cyciopentadiene (CPD) with imines bearing electron-withdrawing substituents are well known and represent a straight forward route to azanorbornenes (4-aza-[2.2.1]bicyclohept-2-enes) (22)(23)(24)(25)(26)(27)(28)(29). Usually a 4]"Is + 2fls reaction occurs, in which CPD represents the diene-component and the imine reacts as a dienophile.…”

Section: Resultsmentioning

confidence: 99%

Chiral Chelating Systems: Unusual Formation and X-Ray-Structure of Rac-3a(r),4(s),5,9b(s)-Tetrahydro-4-(Pyrid-2-Yl)-3h-Cyclopenta[c]quinoline

Wurst¹,

Buchmeiser²

1999

Heterocyclic Communications

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N-Phenyl-2-(pyrid-2-yl)imine reacts with zinc iodide to give the corresponding diiodo zinc imine complex 1. I reacts with cyclopentadiene (CPD) at 0°C under ultrasound-assisted conditions to yield rac3a(R),4(S),5,9b(S)-tetrahydro-4-(pyrid-2-yl)-3//-cyclopenta[c]quino-line 2 instead of N-phenyl-5-aza-6-pyrid-2-ylnorborn-2-ene. The starting imine reacts with CPD in the same way yet more smoothly using BF, Et,0. With both Lewis-acids, the reaction proceeds regio-and distereoselectively. 1 crystallizes in the centrosymmetric space group Pi, a = 8.127 (1), b = 9.133(1), c = 10.467(1) A,"a = 104.36(1)°, β = 100.35(1)°, γ= 95.93(1)°V = 731.4(1) Ä\ Ζ = 2. 2 crystallizes in the centrosymmetric space group P2,/c. a = 10.559(3)), b = 15.061(2), c = 8.252(1) Α, β = 95.90(2)°, V = 13054(4) A 3 , Ζ = 4.

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Section: Resultsmentioning

confidence: 99%

Chiral Chelating Systems: Unusual Formation and X-Ray-Structure of Rac-3a(r),4(s),5,9b(s)-Tetrahydro-4-(Pyrid-2-Yl)-3h-Cyclopenta[c]quinoline

Wurst¹,

Buchmeiser²

1999

Heterocyclic Communications

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“…56 N-(Trichloroethylidene)benzenesulfonamide 2b (yield 40%) and other chloral N-arylsulfonylimines (e.g., 2c,d) were prepared in a similar way. 57 However, an attempt to prepare (N-2,2-dichloroethylidene)arenesulfonamides from N-sulfinyl-4-toluenesulfonamide and dichloroacetaldehyde 32 resulted in the isolation of 1,1-bis-(4-tolylsulfonylamino)-2,2-dichloroethane.…”

Section: B Dehydrochlorination Of Chloro(bromo)polyhaloalkylamidesmentioning

confidence: 99%

N-Functionally substituted imines of polychlorinated (brominated) aldehydes and ketones

Levkovskaya¹,

Drozdova²,

Розенцвейг³

et al. 1999

Russ. Chem. Rev.

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Diels‐Alder Reactions of Imino Dienophiles

et al. 2005

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In comparison to all carbon [4 + 2] cycloadditions, Diesl‐Alder reactions are still in their infancy. The last four decades, however, have seen intensive research in this area. The results if that synthetic organic chemists now have a powerful tool at their disposal for rapid construction of highly functionalized six‐membered nitrogen heterocycles, often in a regio‐, diastereo‐, and enantioselective manner. This chapter encompasses the topic of imine[4 + 2] cycloaddition reactions, of which there are a number of variants. This chapter is limited exclusively to imine and iminium ion dienophiles that undergo inter‐ and intramolecular Diels‐Alder reactions with acylic and cyclic all‐carbon 1,3‐dienes affording 1,2,5,6‐tetrahydropyridines as the initial cycloadducts. In situations where there is a mechanistic ambiguity, such as reactions that proceed via Mannich reactions, these mechanisms are included since it is difficult to know where to draw the line on coverage. A comprehensive discussion of each structural type of imino dienophiles covers the literature up to the middle of 2004. A general overview of mechanistic, regiochemical, and sterochemical considerations is also presented. Specific relevant exo/endo issues, remote diasteroselectivity and the use of chiral auxiliaries are discussed under each separate imine type. Separate sections have also been included that describe intramolecular reactions, as well as more recent advances in enantioselective cycloadditions involving chiral catalysts.

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Synthesis of Heterocyclic Compounds by Cycloaddition Reactions. IV Azomethines as Dienophiles

Cited by 9 publications

References 7 publications

Chiral Chelating Systems: Unusual Formation and X-Ray-Structure of Rac-3a(r),4(s),5,9b(s)-Tetrahydro-4-(Pyrid-2-Yl)-3h-Cyclopenta[c]quinoline

Chiral Chelating Systems: Unusual Formation and X-Ray-Structure of Rac-3a(r),4(s),5,9b(s)-Tetrahydro-4-(Pyrid-2-Yl)-3h-Cyclopenta[c]quinoline

N-Functionally substituted imines of polychlorinated (brominated) aldehydes and ketones

Diels‐Alder Reactions of Imino Dienophiles

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