Cycloadditionen von 6H‐1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 13[1]. Diels‐Alder‐Reaktionen mit 6H‐1,3,4‐Oxadiazin‐6‐onen als Dienophil

Feineis, E.; Schwarz, Harmut; Hegmann, Joachim; Christl, Manfred; Peters, E.‐M.; Peters, Karl

doi:10.1002/cber.19931260734

Cited by 7 publications

References 12 publications

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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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Diels‐Alder Reactions of Imino Dienophiles

et al. 2005

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ChemInform Abstract: Cycloadditions of 6H‐1,3,4‐Oxadiazin‐6‐ones (4,5‐Diaza‐α‐pyrones) . Part 13. Diels‐Alder Reactions with 6H‐1,3,4‐Oxadiazin‐6‐ones as Dienophile.

et al. 1994

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other 6-membered heterocycles other 6-membered heterocycles (with 3 or more heteroatoms) R 0670 -178Cycloadditions of 6H-1,3,4-Oxadiazin-6-ones (4,5-Diaza-α-pyrones) . Part 13. Diels-Alder Reactions with 6H-1,3,4-Oxadiazin-6-ones as Dienophile. -The title compounds (I) and (IV) react as dienophiles with the dienes ( II) and (V) to afford the products (III) and (VI), respectively. An unexpected tricyclic compound (VIII) is obtained with the oxadiazinone (VII). X-Ray structure analyses establish the identity of (VIb) and ( VIII). -(FEINEIS, E.; SCHWARZ, H.; HEGMANN, J.; CHRISTL, M.; PETERS, E.-M.; PETERS, K.; VON SCHNERING, H. G.; Chem.

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Cycloadditionen von 6H‐1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 15.Reaktionen von 6H‐1,3,4‐Oxadiazin‐6‐onen mit Norbornadien. Ein neuer Weg zu 3,6‐disubstituierten α‐Pyronen

Christl¹,

Bodenschatz²,

Feineis³

et al. 1996

Liebigs Ann./Recl.

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Cycloadditionen von 6H-1,3,4-0xadiazin-6-onen (4,5-Diaza-a-pyronen), 1 5L01 Reaktionen von 6H-1,3,4-0xadiazin-6-onen mit Norbornadien. Ein neuer Weg zu 3,6-disubstituierten a-Pyronen* Upon reaction with norbornadiene, ten disubstituted 1,3,4-strates in the absence of boron trifluoride-ether, was aloxadiazin-6-ones l were converted into 3,6-disubstituted a-lowed to react with the Lewis acid. Without use of an acid, pyrones 6. For this purpose, solutions of the substrates were only 6f could be obtained free from further compounds, treated with boron trifluoride-ether or trifluoroacetic acid. whereas in the other cases enol lactones and 1 : 2 products of The smooth formation of 6 was also observed when a y-0x0 the types 8 and 7 were formed additionally. Oxadiazinone ketene, initially generated by heating a solution of the sub-1 j gave enol lactone 10 in the noncatalysed reaction.

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Cycloadditionen von 6H‐1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 13^[1]. Diels‐Alder‐Reaktionen mit 6H‐1,3,4‐Oxadiazin‐6‐onen als Dienophil

Abstract: Cycloadditionen von 6H-1,3,4-0xadiazin-6-onen (4,5-Diaza-a-pyronen), 1 3 ['I

Cited by 7 publications

References 12 publications

Diels‐Alder Reactions of Imino Dienophiles

Diels‐Alder Reactions of Imino Dienophiles

ChemInform Abstract: Cycloadditions of 6H‐1,3,4‐Oxadiazin‐6‐ones (4,5‐Diaza‐α‐pyrones) . Part 13. Diels‐Alder Reactions with 6H‐1,3,4‐Oxadiazin‐6‐ones as Dienophile.

Cycloadditionen von 6H‐1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 15.Reaktionen von 6H‐1,3,4‐Oxadiazin‐6‐onen mit Norbornadien. Ein neuer Weg zu 3,6‐disubstituierten α‐Pyronen

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