New synthetic applications of vinyliminophosphoranes based on the reactivity of the vinyl side chain

Molina, Pedro; Aller, E.; López-Lázaro, Antonia; Alajarı́n, Mateo; Lorenzo, A.

doi:10.1016/s0040-4039(00)73107-8

Cited by 22 publications

(12 citation statements)

References 21 publications

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“…Recently, iminophosphoranes have received increased attention as useful building blocks for the synthesis of nitrogencontaining heterocycles (Molina et al, 1994). The title compound, (I), is an intermediate in the preparation of imidazolinone, which exhibits various biological properties, for example, fungicidal and herbicidal activities (Yang et al, 2004).…”

Section: Commentmentioning

confidence: 99%

(Z)-Ethyl 3-phenyl-2-[(triphenylphosphoranylidene)amino]prop-2-enoate

Huang

Liu

et al. 2005

Acta Cryst E

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Section: Commentmentioning

confidence: 99%

(Z)-Ethyl 3-phenyl-2-[(triphenylphosphoranylidene)amino]prop-2-enoate

Huang

Liu

et al. 2005

Acta Cryst E

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“…Rev., 2011, 40, 2797-2847 2835 has been used as an electrophile. 209,227,245,246 Synthetic utility of iminophosphoranes 385 is hardly investigated. 2 0 -Hydroxya-phosphiminochalcones 344a show an anomalous conjugate addition reaction and yield a five-ring system 387 instead of the expected Michael product (Scheme 78).…”

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confidence: 99%

“…Their treatment with alkyl or aryl iso(thio)cyanates led to benzdiazepinones 390 and benzazepinones 391, respectively, depending on the structure of the R group (Scheme 78). 246 In a short note L'Abbe´and Mathys reported the 1,3-dipolar cycloaddition of diphenylnitrile imine to the double bond of a-azido-a,b-unsaturated ketones 370 leading to the pyrazoles 392 by a hydrazoic acid elimination. 247 The intermediate 393 could also be isolated in one case (Scheme 79).…”

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confidence: 99%

Syntheses and transformations of α-azido ketones and related derivatives

2011

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Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

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“…When different phosphazene groups are in the same molecule, an initial aza-Wittig reaction between the more reactive N-aromatic phosphazene group of bisphosphazene 161 with one equiv of aromatic isocyanate took place, and led to the formation of benzoazepinone compound 164 [62] (Scheme 54). Formation of these compounds can be explained by formation of carbodiimide 162, which undergoes cyclization by nucleophilic attack of the C atom of the N-vinylic phosphazene portion on the central carbon atom of the carbodiimide 162 to give 163 followed by hydrolytic cleavage of phosphazene moiety in 163 affording 1benzodiazepin-5-ones 164.…”

Section: Aza-wittig Reaction With Isocyanates and Isothiocyanatesmentioning

confidence: 99%

N-Vinylic Phosphazenes. A Useful Tool for the Synthesis of Acyclic and Heterocyclic Compounds

Palacios¹,

Aparicio²,

Rubiales³

et al. 2006

COC

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The synthesis and reactivity of the N-vinylic phosphazene derivatives is the subject of this review. The first part gives a survey of different methodologies for the preparation of N-vinylic phosphazenes. These N-vinylic phosphazenes can be prepared either, by Staudinger reaction of N-vinylic azides with phosphines, or by reaction of phosphorus ylides and nitriles. The second part covers the high synthetic potential of these N-vinylic phosphazenes as valuable building blocks in preparative organic synthesis. N-Vinylic phosphazenes can be used as starting materials for the preparation of enamines by hydrolysis under basic or acidic conditions, and can be transformed into aminophosphonium salts by treatment with hydrogen halides or acyl halides. However, the most important synthetic application of N-vinylic phosphazenes is their use for the construction of carbon-nitrogen double bonds by means of aza-Wittig reaction with carbonyl compounds. This aza-Wittig reaction of N-vinylic phosphazenes has been widely applied for the preparation of simple and functionalized 2-aza-1,3-butadienes. These 2-azadienes are excellent starting materials for the construction of acyclic and heterocyclic compounds, and more elaborated polycyclic derivatives. Also the reactivity of N-vinylic phosphazenes with cumulene double bonds as carbon dioxide, carbon disulfide, isocyanates, isothiocyanates, ketenes and triple bonds, and the use of this process for the synthesis of acyclic and cyclic derivatives has been reviewed.

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New synthetic applications of vinyliminophosphoranes based on the reactivity of the vinyl side chain

Cited by 22 publications

References 21 publications

(Z)-Ethyl 3-phenyl-2-[(triphenylphosphoranylidene)amino]prop-2-enoate

(Z)-Ethyl 3-phenyl-2-[(triphenylphosphoranylidene)amino]prop-2-enoate

Syntheses and transformations of α-azido ketones and related derivatives

N-Vinylic Phosphazenes. A Useful Tool for the Synthesis of Acyclic and Heterocyclic Compounds

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