Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones

Fisyuk, A. S.; Poendaev, Nikolai V.

doi:10.3390/70200119

Cited by 10 publications

(4 citation statements)

References 8 publications

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“…Fisyuk, A. S., and Poendaev, N. V. [53] established that intramolecular Darzens reaction of N-(3-oxoalkyl)chloroacetamides, which could make possible the preparation of cis-3,4-epoxypyridin-2-ones, has not been investigated. Thus, they have found that treatment of compounds 81a-e with potassium t-butoxide in a t-butanol and benzene mixture at 0°C afforded the corresponding cis-3,4-epoxypiperidin-2-ones 82a-e in 10-71% yield as a result of an intramolecular Darzens reaction (Scheme 22).…”

Section: Pyrrole Derivativesmentioning

confidence: 99%

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Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Madkour¹,

Elgazwy

2007

COC

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New developments in the utilities of some carbon nucleophiles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of carbon nucleophiles of active methylene are discussed. The major methods and modifications are analyzed. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into a structure, probably the use of a carbon nucleophile analogues are the most direct one. The present review deals with the generation and synthetic of carbon nucleophile, which uses as scaffold for the heterocyclic synthesis, and can be considered as an update review. Therefore the only references published upon the second quarter of 2003 are included, and the same restrictions to the literature coverage apply.

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Section: Pyrrole Derivativesmentioning

confidence: 99%

“…The interaction of compounds 315a-g with PPh 3 under heating in ethanolic or dioxane [53] solutions proceeds with low yields and in some cases is accompanied by the formation of side products. For [189] succeeded in finding of reaction conditions which afforded phosphonium salts 316a-g in 80-90% yields, as shown in Scheme 99.…”

Section: Pyridine Derivativesmentioning

confidence: 99%

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Madkour¹,

Elgazwy

2007

COC

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“…A few years ago we developed the synthesis of 5,6-dihydro-2(1H)-pyridinones and -thiones 6 by intramolecular cyclization of N- (3-oxoalkyl)amides andthioamides 2 [23][24][25][26][27][28][29][30] (Scheme 1). However, only a few examples of cyclization of N-(3-oxoalkenyl)amides 3 to the 2(1H)-pyridinones 7 are known.…”

Section: N-(3-oxoalkyl)amides 2 and N-(3-oxoalkenyl)amides 3 Are Analmentioning

confidence: 99%

Intramolecular cyclization of N-(3-oxoalkenyl)phenylacetamides: synthesis of 3-phenyl-2(1H)-pyridones

Goncharov¹,

Garkushenko²,

Savelieva³

et al. 2015

Arkivoc

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3-Phenyl-2(1Н)-pyridinones were obtained by base-catalyzed intramolecular aldol-type cyclization of N-(3-oxoalkenyl)phenylacetamides. The effect of substituents in the starting compounds and the experimental conditions on the reaction course were established. It was shown that the transformations of N-(3-oxoalkenyl)amides in basic medium depend on structural and electronic factors as well as the reaction conditions.

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“…In order to increase the acidity, various acceptors including a pyridine ring [3, 4], triphenylphosphonium group [5, 6], halogen atom [7], and a tosyl [8] or aryl [9] substituent were introduced to the -carbamoyl position. It is possible to introduce a divalent sulfur atom in order to stabilize the carbanion and so increase the acidity at the -carbamoyl position.…”

mentioning

confidence: 99%

Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*

Fisyuk

Bogza

Poendaev

et al. 2010

Chem Heterocycl Comp

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oxoalkenyl)amides which contain a divalent sulfur atom in an -position to a carbamoyl group and bound to the heterocycle.We have previously reported that N-(3-oxoalkenyl)-and N-(3-oxoalkyl)amides containing a mobile hydrogen atom in an -position to the carbamoyl group can undergo an aldol type intramolecular ring closure to give pyridin-2(1H)-ones [1] or their hydrogenated derivatives [2]. In order to increase the acidity, various acceptors including a pyridine ring [3, 4], triphenylphosphonium group [5, 6], halogen atom [7], and a tosyl [8] or aryl [9] substituent were introduced to the -carbamoyl position. It is possible to introduce a divalent sulfur atom in order to stabilize the carbanion and so increase the acidity at the -carbamoyl position. In our case, this can be achieved by the nucleophilic substitution of the halogen in N-(3-oxoalkenyl)-and N-(3-oxoalkyl)-chloroacetamides by a thio group. At the same time the use of thiophenol and thiols in the synthesis is not without the drawback of an unpleasant odor. The introduction of a divalent sulfur atom in the molecule is possible by the S-alkylation of cyclic thioamides, thiocarbamates, or thiourea. The compounds are generally crystalline and do not have an objectionable odor. We have previously reported such a possible route [10].With the aim of studying the cyclization of N-(3-oxoalkenyl)-and N-(3-oxoalkyl)amides containing a divalent sulfur atom in an -carbamoyl position we have prepared the compounds 4a, 5a-e by treating the chloroacetamides 1, 2 (synthesized by known methods [1,9]) with the thio derivatives 3a-e. The reactions were carried out in DMF at room temperature in the presence of potassium carbonate and potassium iodide. The completion of the reaction was monitored by TLC. The yields of compounds 4a and 5a-e were 54-88% (Table 1).It was found that cyclization of compounds 5a,d occurs even at room temperature over 2-3 h with the action of sodium ethylate in ethanol to give the 5,6-dihydropyridin-2(1H)-ones 7a,d in 80-90% yield. Cyclization of compounds 5b,c,e occurs more slowly and it is necessary to carry out the reaction with heating.

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Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones

Cited by 10 publications

References 8 publications

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Intramolecular cyclization of N-(3-oxoalkenyl)phenylacetamides: synthesis of 3-phenyl-2(1H)-pyridones

Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*

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