An Efficient Approach to the Synthesis of Alkyl 7-Hydroxy-1-oxo-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylates via a One-Pot, Three-Component Reaction

Alizadeh, Abdolali; Abadi, Marziyeh Hossein; Ghanbaripour, Rashid

doi:10.1055/s-0034-1378275

Cited by 9 publications

(4 citation statements)

References 6 publications

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“…Alizadeh and co-workers have developed an efficient method for the synthesis of alkyl 7-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2- a ]pyrazine-8-carboxylate derivatives via the three-component reactions of diamines, dialkyl acetylenedicarboxylates, and alkyl or aryl glyoxals in the presence of p -toluenesulfonic acid (10 mol%) under reflux conditions (Scheme 96 ). 102…”

Section: Synthesis Of Polycyclic Compoundsmentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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Activated acetylenic substrates such as acetylenic esters and alkyl propiolates are very important in organic synthesis. Due to their electron deficiency, these compounds are widely used in combinatorial and multicomponent reactions, enabling the synthesis of a large variety of novel compounds. In addition, these substrates are powerful Michael acceptors and convenient dienophiles and dipolarophiles in Diels–Alder and 1,3-dipolar cycloaddition reactions. The addition of different nucleophiles, primarily phosphorus, nitrogen or sulfur, to the triple bonds of these substrates produces key intermediates, such as Tebby and Huisgen zwitterions, which can lead to designing pathways toward the generation of spirocyclic and polycyclic compounds. This account highlights recent studies on the chemistry of acetylenic esters and their applications in organic synthesis.1 Introduction2 Synthesis of Acyclic and Monocyclic Compounds3 Synthesis of Spirocyclic Compounds4 Synthesis of Polycyclic Compounds5 Conclusion

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Section: Synthesis Of Polycyclic Compoundsmentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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“…Thus, reaction with bromopyruvate in acetonitrile or water at reflux resulted in diester 118 [117,118]. On the other hand, reactions with nitrostyrene, catalyzed by sulfamic acid (SA) in acetonitrile [119] or Fe 3 O 4 @SiO 2 -OSO 3 H magnetic nanoparticles in water [40] afforded aryl derivatives 119, and condensation with methyl-or arylglyoxal in ethanol at reflux with p-toluenesulfonic acid (TsOH) catalysis gave hydroxyl derivatives 120 [120] (Scheme 32).…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones

et al. 2021

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Dihydropyrrolo[1,2-a]pyrazinone rings are a class of heterocycles present in a wide range of bioactive natural products and analogues thereof. As a direct result of their bioactivity, the synthesis of this privileged class of compounds has been extensively studied. This review provides an overview of these synthetic pathways. The literature is covered up until 2020 and is organized according to the specific strategies used to construct the scaffold: fusing a pyrazinone to an existing pyrrole, employing a pyrazinone-first strategy, an array of multicomponent reactions and some miscellaneous reactions.

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“…所合成的 12 个哌嗪酮取代醌类衍生物 3a～ 3l 的具体结构及产率见表 2. [20] 互变形成中间体 6, 化合物 6 经过酮-烯醇互变形成化合物 7, 化合物 7 被原料 2c 氧化生成目标烯胺酯取代的醌类化合物 3i, 而原料 2c 被还原为萘酚 8, 萘酚 8 长时间在空气中被氧气氧化成原料 2c, 从而完成整个循环过程(Scheme 2). 10, 160.86, 151.66, 148.23, 138.27, 137.28, 130.93, 90.40, 51.96, 40.21, 39.59;IR (KBr) ν: 3305, 3257, 2953, 2867, 1643, 1594, 1485, 1460, 1440, 1283 187.41, 169.24, 160.99, 151.29, 146.94, 145.77, 134.32, 131.64, 91.45, 60.40, 40.32, 40.19, 16.00, 14.69;IR (KBr) ν: 3350, 3197, 3087, 2911, 2871, 1688, 1620, 1602, 1585, 1482 187.…”

Section: 目标产物及收率unclassified

Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives

Yang¹,

Zhao²,

Meiyu³

et al. 2016

Chin. J. Org. Chem.

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In this article, a one-pot protocol was established for the synthesis of ketopiperazine-substituted quinone derivatives. This method based on the building blocks of piperazine ketone enamine ester 1, which reacted with quinones 2 through α-C selective alkylation of the enamine ester and via dehydrogenation oxidation reaction in acetonitrile at room temperature and acetic acid as catalyst. As a result, a series of novel ketopiperzine-substituted quinone derivatives 3a～3l have been synthesized efficiently with 70%～88% yield. This method possesses some advantages such as simple synthetic route, readily available starting materials, high yields and simple work-up procedures.

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An Efficient Approach to the Synthesis of Alkyl 7-Hydroxy-1-oxo-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylates via a One-Pot, Three-Component Reaction

Cited by 9 publications

References 6 publications

Acetylenic Esters in Organic Synthesis

Acetylenic Esters in Organic Synthesis

A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones

Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives

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