Transformation of Some Aryl, Benzyl Ketones to 2-Aryl-1,3-Dichloroindenes by Vilsmeier Reagent

Elliott, I. W.; Evans, S. L.; Kennedy, Lorna; Parrish, A. E.

doi:10.1080/00304948909356401

Cited by 9 publications

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“…compound 10 by treatment with TSH Ĳp-toluenesulphonyl hydrazide). Then, tosylhydrazone 10 reacted with the appropriate benzaldehydes to generate the deoxybenzoins 12a-e. 16 A Vilsmeier reaction of the deoxybenzoins 12a-e generates mixtures of the (E)-and ĲZ)-3-chloro-2,3-diarylacrylaldehydes 13a-e. 17 Subsequently, 13a-e reacted with ethyl thioglycolate and then underwent cyclisation under basic conditions to produce the esters 3a-e. 18 After hydrolysis, the acids 4a-e were obtained and were then decarboxylated to generate compounds 5a-e. 19 Compounds 3e, 4e, and 5e were debenzylated using TiCl 4 to produce compounds 3f, 4f, and 5f, respectively. 20 The target compounds 6a-d, 7a-d, and 8a-d were synthesised according to Scheme 2.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4

et al. 2015

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Dimethylchloromethyleneammonium Chloride

Giles¹,

Marson²

2001

Encyclopedia of Reagents for Organic Synthesis

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The Vilsmeier Reaction of Non‐Aromatic Compounds

Jones

Stanforth

2000

Organic Reactions

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This chapter extends the discussion to reactions between the Vilsmeier‐Haack reagent (subsequently referred to as the Vilsmeier reagent for brevity) and any other compounds in which a carbon‐carbon bond is formed. The discussion thus excludes reactions in which the Vilsmeier reagent acts as a chlorinating agent (for example in the preparation of acid chlorides), or in which it forms carbon‐oxygen or carbon‐nitrogen bonds, unless these are accompanied by formation of a carbon‐carbon bond. For a discussion of the nature of the reagent and of the mechanism of the reaction, the earlier chapter in vol. 49 should be consulted. There are also a number of reviews that deal at length with mechanisms of reactions involving the Vilsmeier reagent, notably those by Jutz and Marson, and hence this chapter will concentrate on applications, with brief mention of mechanisms when necessary. Wizinger has pointed out that alkenes could react with the Vilsmeier reagent, but his only examples were styrenes where the intermediate carbocation has considerable stability. Hydrolysis gives the cinnamaldehyde. In principle, any alkene which is not too sterically hindered can undergo this reaction, but the Vilsmeier reagent has low reactivity as an electrophile, and in practice activation is often necessary. The addition depends on the HOMO of the alkene, and anything increasing the HOMO energy will aid reaction, as for example further conjugation (dienes, trienes, etc.) or the presence of an electron‐donating substituent. Hence aldehydes and ketones are active in their enol forms, and enol ethers and enamines are good substrates. Indeed, all additions covered by this chapter can be regarded as alkene additions, even those on active methyl groups attached to electron‐deficient rings. As with any reaction involving carbocation intermediates, rearrangements are possible; the initial products are sometimes enamines, and this can give rise to polysubstitution. The substrates are grouped into eleven major subsections; references to reviews of particular relevance will be found in the appropriate subsection.

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Transformation of Some Aryl, Benzyl Ketones to 2-Aryl-1,3-Dichloroindenes by Vilsmeier Reagent

Cited by 9 publications

References 3 publications

Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4

Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4

Dimethylchloromethyleneammonium Chloride

The Vilsmeier Reaction of Non‐Aromatic Compounds

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