Synthesis of Oudenone and Its Related Compounds

Tsujikawa, Teruaki; Nakagawa, Tasushi; Tsukamura, Kazuo; Masuda, Kazuaki

doi:10.3987/r-1977-03-0261

Cited by 10 publications

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“…We required the title compound, (I), a simple example of this type of enaminone, as a precursor in our ongoing programme aimed at the total synthesis of indolizidine alkaloids (Michael et al, 1999). The compound has previously been prepared by condensing pyrrolidin-2-onederived lactim ethers, thioethers or amide acetals with ethyl acetoacetate (Tsujikawa et al, 1977;Singh et al, 1984;Brunerie et al, 1986).…”

Section: Commentmentioning

confidence: 99%

Ethyl (2E)-3-oxo-2-(pyrrolidin-2-ylidene)butanoate

2007

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Section: Commentmentioning

confidence: 99%

Ethyl (2E)-3-oxo-2-(pyrrolidin-2-ylidene)butanoate

2007

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“…This reaction, however, in contrast to the above mentioned example, takes place exclusively at the carbonyl groups. (8) Meinwald, J.; Mioduski, J. Tetrahedron Lett. 1974, 15, 4137.…”

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Syntheses with cyclobutadienes. 8. Cycloaddition of o-benzoquinone to a kinetically stabilized cyclobutadiene

Juergen¹,

Maas²,

Regitz³

1985

J. Org. Chem.

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Twofold Extrusion Reactions

Guziec

2012

Organic Reactions

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Twofold extrusion reactions are chemical transformations in which two small inorganic molecules or atoms connecting carbon or nitrogen atoms are lost, generating the corresponding carbon‐carbon or carbon‐nitrogen double bonds. These reactions are particularly useful for the preparation of sterically hindered alkenes and imines. The inorganic species liberated in twofold extrusion reactions can be molecular nitrogen, sulfur, selenium, tellurium, sulfur dioxide, sulfur monoxide, carbon dioxide or carbon monoxide. The most common precursors for twofold extrusion reactions are 1,3,4‐thiadiazolines, which thermally extrude molecular nitrogen affording thiiranes. These thiiranes can be readily desulfurized to afford the corresponding alkenes using tertiary phosphines. The corresponding 1,3,4‐selenadiazolines thermally extrude both molecular nitrogen and atomic selenium directly affording alkenes. Alkenes can also be prepared by formal extrusions of molecular nitrogen plus sulfur dioxide or sulfur monoxide. Extremely sterically hindered imines can be prepared by extrusions of molecular nitrogen and sulfur or selenium from in situ generated heterocyclic precursors. Other less common twofold extrusion reactions are also reported. The detailed preparations of the required precursors for the twofold extrusion reactions as well as the mechanisms of these extrusion processes are discussed in this chapter. The utility of twofold extrusion reactions in the preparations of ‘molecular rotors’ and other extremely sterically hindered alkenes is presented. The steric limitations of the twofold extrusion reactions are discussed along with comparisons of these reactions with other alkene‐ and imine‐forming synthetic methods. The Tabular Survey covers material through the end of 2009.

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Synthesis of Oudenone and Its Related Compounds

Cited by 10 publications

References 0 publications

Ethyl (2E)-3-oxo-2-(pyrrolidin-2-ylidene)butanoate

Ethyl (2E)-3-oxo-2-(pyrrolidin-2-ylidene)butanoate

Syntheses with cyclobutadienes. 8. Cycloaddition of o-benzoquinone to a kinetically stabilized cyclobutadiene

Twofold Extrusion Reactions

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