Addition, substitution and deoxygenation reactions of .alpha.-phenyl-.beta.-nitrostyrenes with the anions of thiols and diethyl phosphite: formation of indoles by reaction with ethyl phosphites

Russell, Glen A.; Yao, Ching Fa; Tashtoush, Hasan; Russell, J. E.; Dedolph, D. F.

doi:10.1021/jo00002a032

Cited by 40 publications

(9 citation statements)

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“…19 2-Nitroindoles have been synthesized directly through the thermolysis of b-substituted-o-azidostyrenes: 2-nitroindole itself was obtained in three steps from 2-nitrobenzaldehyde in 40% overall yield. 20,21 The ability to nitrate specifically at the 2-position is a new approach to 2-nitro-indoles that is extremely quick, clean and high yielding (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

The nitration of some 4,6-dimethoxyindoles

et al. 2004

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Section: Resultsmentioning

confidence: 99%

The nitration of some 4,6-dimethoxyindoles

et al. 2004

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“…The above-mentioned study was followed by other authors [9], who reported the addition reaction of triethylphosphite tonitrostyrene 12. As reported in Scheme 7, reaction of nitroalkene 12 with 3.2 equivalents of triethylphosphite leads to a mixture of diphosphonate 16, nitrile 17 and phosphorylated oximes 18 and 19 as traces.…”

Section: Nucleophilic Addition Of Phosphorus Reagents To Nitro Olefinsmentioning

confidence: 89%

β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

Santos¹,

Vicario²,

Alonso³

et al. 2011

COC

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The purpose of this review article is to illustrate synthetic aspects of functionalized phosphorus derivatives containing an oximo moiety at the beta-position. First section will be focused on the synthesis of phosphine oxides, phosphonates or phosphonium salts containing an oxime group. The synthesis of these derivatives comprises the carbon-phosphorus single bond construction by reaction of haloximes with phosphorus derivatives, nucleophilic addition of phosphorus reagents to carbonyl compounds, or nucleophilic addition of phosphorus reagents to nitro olefins. This section will also concentrate on the most practical routes for the synthesis of the target compounds, through carbon-nitrogen double bond formation, which are as follows: condensation processes of carbonyl compounds and hydroxylamine derivatives or addition of hydroxylamines to allenes or alkynes. The preparative use of beta-oximo phosphorus derivatives as synthetic intermediates will be discussed in a second section, comprising olefination reaction, oxidation of oximes to nitrile oxides by reaction at the C-N double bond of the oxime moiety, oxidation of these substrates to nitrosoalkenes, reduction to the corresponding hydroxylamines and some reactions at the hydroxyl group of the hydroxyimino moiety.

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“…Person of the Université de Rennes found 45 that exposure of a β-nitro styrene 94 (Scheme 36) to an isonitrile 95 led to the N -hydroxy indole 96 . Glen A. Russell of Iowa State University reported 46 a related reductive cyclization of a β-nitro styrene with triethyl phosphite.…”

Section: Typementioning

confidence: 99%