Reactions of Enamines. V. The Acylation of Enamino Ketones<sup>1</sup>

Alt, G. H.; Speziale, A. J.

doi:10.1021/jo01027a008

Cited by 24 publications

(10 citation statements)

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“…The 2-acetyl-5,5-dimethyI-3-N-pyrrolidylcyclohex-2-en-1-one (8) was prepared according to the method of Alt and Speziale (6). The preparation of 2-aminoacetyldimedone (10) was reported recently (7).…”

Section: Amino Deriuatiues Of 2-acetyfdimedonementioning

confidence: 99%

“…All the amino-chelocardin derivatives obtained according to the route described (3) show an additional absorption at approximately 307-312 nm in their uv spectra, indicating the formation of a vinylogous imide system (6). Their mass spectra show the presence of several fragments normally found in the mass spectrum of chelocardin; the most important and prominent ion can be assigned to structure B shown in Fig.…”

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confidence: 93%

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Chemistry of chelocardin. V. Condensation with amino reagents

Chu¹,

Huckin²,

Bernstein³

et al. 1981

Can. J. Chem.

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Section: Amino Deriuatiues Of 2-acetyfdimedonementioning

confidence: 99%

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confidence: 93%

Chemistry of chelocardin. V. Condensation with amino reagents

Chu¹,

Huckin²,

Bernstein³

et al. 1981

Can. J. Chem.

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“…On the other hand, high yields are usually observed in ordinary acylation reactions when triethylamine is used as a base to prevent salt formation. 7) The attempts to realize the trichloroacetylation of the same enamines by using triethylamine without using zinc gave monoacylation products as in the literature.…”

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confidence: 96%

“…Compound 3 has been directly synthesized by the reaction of morpholine in chloroform with hexachloroacetone, in the literature. 9) In case of cyclopentanone enamines under the same reaction conditions, both the 1-(4-morpholino)cyclopentene (1b) and 1-(1-pyrrolidinyl)cyclopentene (1d) were converted directly to the corresponding triketone, 2,6-di(trichloroacetyl)cyclopentanone (7), in 45 and 55% yields, respectively. The reaction of compound 1b also gave N-acetylated product, compound 3, in 35% yield.…”

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confidence: 99%

Trichloroacetylation of Some Cyclic Enamines.

Şenöz

Tunoglu

2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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The pyrrolidine and morpholine enamines of cyclic ketones such as cyclohexanone and cyclopentanone were successfully diacetylated at alpha- and alpha'-positions with trichloroacetyl chloride using zinc catalyst. Morpholine enamines of the cyclic ketones gave acetylated morpholine in good yields besides the corresponding diacetylated cyclic enamines. When the same reactions were performed by using triethylamine without using zinc, monoacetylation products of the same enamines were synthesized.

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“…The importance of nucleophilicity of the nitrogen to form enamines has been documented and it can be determined by stereoeletronic effects of amines. [41][42][43][44] As shown in Table 1, the reactions where more nucleophilic amines were used (i.e. benzylamine, cyclohexylamine, and hexylamine) gave the products in almost quantitative yields in a short period of time.…”

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confidence: 99%