Solid-Phase Synthesis of 1,2,3,4-Tetrahydro-2-pyridones via Aza-Annulation of Enamines

Paulvannan, K.; Chen, Tao

doi:10.1021/jo000676c

Cited by 46 publications

(13 citation statements)

References 65 publications

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“…The title molecules have been prepared by numerous methods [21], e.g., oxidation of N -substituted pyridinium salts [22], by means of Knoevenagel-type reactions [23] such as the cross-condensation of cyanoacetoamide and β-dicarbonyl compounds with basic catalysts or by the reaction of 2-pyrones with amides. Despite the large number of known methods for their synthesis, the importance of this class of molecules means that new procedures must always be welcomed, in particular using suitable green techniques [24–26], in order to be less aggressive to the environment.…”

Section: Introductionmentioning

confidence: 99%

Infrared Assisted Production of 3,4-Dihydro-2(1H)-pyridones in Solvent-Free Conditions

Noguez¹,

Marcelino²,

Rodríguez

et al. 2011

IJMS

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A green approach for the synthesis of a set of ten 4-aryl substituted-5-alcoxy carbonyl-6-methyl-3,4-dihydro-2(1H)-pyridones using Meldrum’s acid has been devised, the absence of solvent and the activation with infrared irradiation in addition to a multicomponent protocol are the main reaction conditions. The transformations proceeded with moderated yields (50–75%) with a reasonable reaction rate (3 h). It is worth noting that two novel molecules of the new class of the bis-3,4-dihydropyridones were also obtained. In addition, a comparison without the use of infrared irradiation was performed.

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Section: Introductionmentioning

confidence: 99%

Infrared Assisted Production of 3,4-Dihydro-2(1H)-pyridones in Solvent-Free Conditions

Noguez¹,

Marcelino²,

Rodríguez

et al. 2011

IJMS

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“…Синтез δ-лактамів 1.3.1. Каталітичні електрофільні циклізації Найтиповішим представником δ-лактамних систем є піридин-2-они, а також їх ди-та тетрагі-дропохідні, структурні фрагменти яких входять до складу різноманітних алкалоїдів та біоактив-них молекул [14].…”

Section: синтез γ-лактонів та лактамівunclassified

Heterocyclization of amides of alkenylcarboxylic acids

Tsyzoryk¹,

Васькевич²,

Вовк³

2015

J. org. pharm. chem.

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(Ховейда, Граббса, Нолана), реакції мета-тезису, а також радикальних процесів у регіо-та стереоселективних циклізаціях амідів у м'яких умовах. Розглянуті синтетичні варіанти носять загальний характер і дозволяють поряд із процесами циклізації здійснювати спрямовану функціоналізацію O-, N-, S-вмісних малих та середніх гетероциклічних систем. HETEROCYCLIZATION OF AMIDES OF ALKENYLCARBOXYLIC ACIDS N.M.Tsyzoryk, A.I.Vaskevich, M.V.Vovk Key words: amides of alkenylcarboxylic acids; electrophilic intramolecular cyclization; lactones; lactams The latest published data on heterocyclization of amides of alkenylcarboxylic acids have been systematized. It has been proven that the electrophilic intramolecular cyclization reaction of functionally substituted olefins opened in the 70s of the last century is a convenient way of constructing different oxygen-, nitrogen-and sulfurcontaining heterocyclic compounds. It has been noted that anilides of unsaturated carboxylic acids as bifunctional nucleophilic systems containing alkenyl and aminocarbonyl functions are useful models to study the electrophilic cyclization reaction, which leads to formation of O-and N-containing heterocycles (lactones and lactams). The last of them belong to the important types of compounds used as key blocks in the synthesis of biologically active alkaloids and their analogues, pharmaceutical and agrochemical products. The effective approaches to the synthesis of new types of functionalized lactones and lactams have been developed; amides of 3-butenoic, 4-pentenoic and 5-hexenoic acids are often used as substrates for their design. Along with classical methods of synthesis of lactones and lactams the literary sources relating to the use of original catalytic electrophilic systems (Nolan, Grubbs, Hoveyda), the metathesis reaction and radical processes in regio-and stereoselective cyclization of amides under mild conditions have been analyzed and summarized in the article. The synthetic versions considered are general in nature and allow to perform the targeted functionalization of O-, N-, S-containing heterocyclic small and medium-sized systems along with the cyclization processes. ГЕТЕРОЦИКЛИЗАЦИИ АМИДОВ АЛКЕНИЛКАРБОНОВЫХ КИСЛОТ

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“…In addition, slight modification of the 4,6-diaryl-2-pyridone nucleus was reported to afford a series of 3-unsubstituted 2-pyridone derivatives [5,[9][10][11] (B) which provide new series of biologically active compounds. Substituted six-membered lactams, 2-pyridones, and their 3,4-dihydro derivatives have also attracted considerable attention from synthetic organic chemists since these scaffolds are found in a wide variety of naturally occurring alkaloids [12] and compounds with these structural motifs have been shown to exhibit significant pharmacological properties [13], for example dihydro-2-pyridones have been applied as scaffolds to the construction of constrained amino acid [14]. However, little attention has been paid to the synthesis of 3,4-dihydro-4,6-diaryl-2-pyridones which are unsubstituted on the 3-and 5-positions.…”

Section: Introductionmentioning

confidence: 99%

An efficient microwave‐assisted synthesis of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives

Zhu

Shi

et al. 2007

Journal of Heterocyclic Chem

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Small libraries of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives were synthesized from the condensation‐products of aldehydes with Meldrum's acid, aromatic ketones and ammonium acetate using acetic acid as energy transferring‐agent under microwave irradiation without catalyst. This method has the advantages of excellent yields (65‐90%), short reaction time (5‐10 min) and being environmentally friendly. It aimed to provide new series of potential biologically active compounds for biomedical screening.

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Solid-Phase Synthesis of 1,2,3,4-Tetrahydro-2-pyridones via Aza-Annulation of Enamines

Cited by 46 publications

References 65 publications

Infrared Assisted Production of 3,4-Dihydro-2(1H)-pyridones in Solvent-Free Conditions

Infrared Assisted Production of 3,4-Dihydro-2(1H)-pyridones in Solvent-Free Conditions

Heterocyclization of amides of alkenylcarboxylic acids

An efficient microwave‐assisted synthesis of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives

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