2-Oxoindolin-3-ylidene derivatives as 2π components in 1,3-dipolar cycloadditions of azomethine ylides

Fejes, Imre; Nyerges, Miklós; Szöllősy, Áron; Bogáts, Gábor; Tőke, Lásʐló

doi:10.1016/s0040-4020(00)01085-1

Cited by 56 publications

(16 citation statements)

References 33 publications

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“…We also found that three-component reactions of N -benzylbenzimidazolium salts, isatins and malononitrile or ethyl cyanoacetate gave a series of the novel zwitterionic salts and the unexpected products with opening of the imidazole ring58. These results together with the previously reports596061626364 indicated that the 1,3-dipolar cycloaddition reactions of cyclic nitrogen N -ylides with 3-methyleneoxindoles have fruitful chemistry. Due to the spirooxindole existing in a large number of naturally occurring and medicinally relevant substances, the development of efficient method for constructing the spirooxindole motif is of great importance in synthetic organic and medicinal chemistry6566676869707172.…”

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confidence: 69%

Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile

Sun

Shen

Huang

et al. 2017

Sci Rep

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The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2′-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2″,3″:2′,3′]pyrrolo[3′,4′:4,5]pyrrolo[2,1-a]isoquinoline derivatives. However, the three-component reaction of N-cyanomethylisoquinolinium chloride, isatins and ethyl cyanoacetate mainly resulted in functionalized spiro[indoline-3,8′-pyrido[2′,3′:4,5]pyrrolo[2,1-a]isoquinolines].

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confidence: 69%

Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile

Sun

Shen

Huang

et al. 2017

Sci Rep

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“…Methods for the construction of the 3,3 -spirooxindole core The 1,3-dipolar cycloadditions of azomethine ylides to 2-oxoindolin-3-ylidene derivatives were investigated by a number of authors [57,58]. Methyl oxindolylidene acetate 67 can be used as a 2-π component in reactions with a wide range of different azomethine ylides generated in situ from sarcosine 63 and the corresponding carbonyl compounds (6-phenyl-4H -pyran-4-one-2-carbaldehyde 68, aldehydes 69-72 and isoquinolinium bromide 73) (Scheme 15).…”

Section: 3-dipolar Cycloaddition Reactions In the Synthesis Of Spirmentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

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“…This is particularly important for azomethine ylides and carbonyl ylides, which are prone to isomerisation. 65 When two chiral centres are formed during the cycloaddition, one arising from the dipole and one arising from the dipolarophile, diastereomeric products (cis-and trans-) may be produced via endo and exo transition states ( Figure 5). Secondary orbital interactions have been used to explain the stereoselectivity of a large number of 1,3-dipolar cycloadditions.…”

Section: Stereoselectivitymentioning

confidence: 99%

Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references)

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2-Oxoindolin-3-ylidene derivatives as 2π components in 1,3-dipolar cycloadditions of azomethine ylides

Cited by 56 publications

References 33 publications

Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile

Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile

Molecular diversity of spirooxindoles. Synthesis and biological activity

Asymmetric 1,3-dipolar cycloadditions of acrylamides

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