Aroylations at the Methyl Group of Benzoylacetone and Related β-Diketones with Esters to Form 1,3,5-Triketones by Sodium Hydride. Other Terminal Condensations<sup>1</sup>

Miles, Marion L.; Harris, Thomas M.; Hauser, Charles R.

doi:10.1021/jo01015a013

Cited by 81 publications

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“…The acylation of the dianion of P-diketones has been the subject of several investigations in the past decade or so (1)(2)(3)(4)(5)(6)(7)(8)(9). This has been the most extensively investigated reaction of carbonyl multiple carbanions but it has also proved to be the most challenging and difficult to achieve in good yield.…”

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confidence: 99%

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The Acylation of β-Keto Ester Dianions

Huckin¹,

Weiler²

1974

Can. J. Chem.

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A method for the successful acylation of the dianion of simple β-keto esters to yield β,δ-diketo esters has been developed. The dianion of methyl acetoacetate also reacts with the monoanion of methyl acetoacetate to give a triketo ester which cyclizes to methyl orsellinate. These dianions also add to nitriles to give 5-amino-3-keto-4-pentenoates which may in some cases cyclize to 4-hydroxypyridones.

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“…The yield of aroylation product (6, R"= Aryl) can be very good using sodium hydride as the base in reaction 1 (5). However, this method is apparently limited to aroylations only.…”

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The Acylation of β-Keto Ester Dianions

Huckin¹,

Weiler²

1974

Can. J. Chem.

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“…Several possible mechanisms for the related aroylations of P-diketones have previously been considered (4), and analogous mechanisms might also be possible for the present aroylations of imides and P-keto amides.…”

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confidence: 84%

C-Aroylations of imides and N-aroylations of β-keto amides with aromatic esters by means of sodium hydride to form β-keto imides

Wolfe¹,

Trimitsis²,

Hauser³

1968

Can. J. Chem.

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Aroylations a t the methyl groups of N-acetylbenzamide and p-benzoylaminoacetophenone, and at a inethylene position of succinimide with appropriate aromatic esters were effected by means of sodium hydride in refluxing monoglyme. Benzoylation at the amide group of a-benzoylacetamide and salicylamide were accomplished similarly. The yields of 13-keto imides from these C-and N-aroylations by sodium hydride, with which intermediate dianions were evidently not formed, were generally much better than those obtained through dianions produced by means of an alkali amide in liquid ammonia. The synthetic utility of the sodium hydridemethod is discussed.

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“…In continuation of our investigations we have synthesized pyrone sulfonium ylides, arene carbaldehydes 4a, b and corresponding trans-epoxides.Arylpyrones 1a and 1b were prepared according to the literature in two steps [22]. Bromination of pyrones 1(a-c) with N-bromosuccinimide (NBS) produced the corresponding bromopyrones 2(a-c) in 55-70% yields respectively [23].…”

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Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides

Shahrisa

Saraei

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Hexaminium salts of 4-pyrones 3a, b were synthesized by treatment of 2-(4-bromomethylphenyl)-6-methyl-4H-pyran-4-one 2a and 2-(4-bromomethylphenyl)-6-phenyl-4H-pyran-4-one 2b with hexamethylenetetramine in chloroform in 71 and 84% yields respectively. Hydrolysis of 3a and 3b in EtOH:H 2 O produced the corresponding aldehydes 4a and 4b in 43 and 58% yields respectively. The reaction of bromopyrones 2b and 2c with dimethylsulfide in MeOH: CH 2 Cl 2 afforded the corresponding sulfonium salts 5b and 5c in 66 and 65% yields respectively. Treatment of 5b and 5c with arene carbaldehydes such as (Ar ¼ p-ClC 6 H 4 , o-ClC 6 H 4 , p-NO 2 C 6 H 4 , o-NO 2 C 6 H 4 , p-FC 6 H 4 , 2-naphthyl, p-MeOC 6 H 4, C 6 H 5 CH¼ ¼CH, p-MeC 6 H 4 , C 6 H 5 and 4-(4-oxo-6-phenyl-4H-pyran-2-yl)-benzaldehyde 4b) in the presence of sodium hydroxide in CH 3 CN:H 2 O afforded eleven trans-epoxides in 61-93% yields.

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Aroylations at the Methyl Group of Benzoylacetone and Related β-Diketones with Esters to Form 1,3,5-Triketones by Sodium Hydride. Other Terminal Condensations¹

Cited by 81 publications

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The Acylation of β-Keto Ester Dianions

The Acylation of β-Keto Ester Dianions

C-Aroylations of imides and N-aroylations of β-keto amides with aromatic esters by means of sodium hydride to form β-keto imides

Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides

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Aroylations at the Methyl Group of Benzoylacetone and Related β-Diketones with Esters to Form 1,3,5-Triketones by Sodium Hydride. Other Terminal Condensations1

Cited by 81 publications

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The Acylation of β-Keto Ester Dianions

The Acylation of β-Keto Ester Dianions

C-Aroylations of imides and N-aroylations of β-keto amides with aromatic esters by means of sodium hydride to form β-keto imides

Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides

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Aroylations at the Methyl Group of Benzoylacetone and Related β-Diketones with Esters to Form 1,3,5-Triketones by Sodium Hydride. Other Terminal Condensations¹