A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters

Yavari, Issa; Baoosi, Leila; Halvagar, Mohammad Reza

doi:10.1055/s-0036-1591855

Cited by 10 publications

(9 citation statements)

References 6 publications

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“…After work up, instead of formation of the desired seven-membered spirooxindole, the chain product 2-(oxoindolin-3-ylidene)propylidene)pyrrolidin-1-yl)acrylate ( 1a ) was obtained in 78% yield. The formation of chain product 1a showed that two molecules of methyl propiolate took part in the reaction and that methyl propiolate played a different role in the reaction than dimethyl acetylenedicarboxylate. − A literature survey indicated that 2-(oxoindolin-3-ylidene)propylidene)pyrrolidin-1-yl)acrylate was prepared from various reactions of methyl propiolate for the first time. Thus, the scope of this reaction was examined by using various N -alkylisatins.…”

Section: Resultsmentioning

confidence: 99%

Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin

et al. 2018

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The multicomponent reaction of L-proline, isatins, and excess of methyl propiolates in methanol unexpectedly afforded 2-(oxoindolin-3-ylidene)propylidene)pyrrolidin-1-yl)acrylates in good yields, and the products subsequently converted to unique nine-membered pyrrolo[1′,2′:1,9]azonino [6,5,4-cd]indoles in the presence of p-TsOH. Furthermore, the multicomponent reaction of L-proline, N-benzylisatins, and excess alkyl propiolates in refluxing chloroform unprecedentedly resulted in eight-membered azocino[1,2-a]benzo[c][1,5]diazocines as the main product. The molecular structures of the polyheterocyclic compounds were confirmed by determination of 19 single crystal structures. The reaction mechanism was believed to contain the sequential 1,3-dipolar cycloaddition, addition of cyclic tertiary amine to excess of propiolate, and fascinating ring opening as well as rearrangement process. The N-substituent on isatins played a critical role in the different reaction patterns.

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Section: Resultsmentioning

confidence: 99%

Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin

et al. 2018

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“…Next, the 1,3-dipolar cycloaddition was carried out between the azomethine ylide and the dialkyl acetylenedicarboxylate to produce dialkyl (12E,14E)-7-oxo-10,11-dihydro-7H,9H-azocino[2,1a]benzo[de]isoquinoline-13,14-dicarboxylates in yields of 67-83%. 95 In 2018, Yavari and co-workers described a simple route for the synthesis of new perinaphthenones from the reactions of acetylenic esters and acenaphthoquinone-malononitrile adducts by employing a catalytic amount of PPh 3 in CH 2 Cl 2 at 0-25 °C (Scheme 90). Initially, PPh 3 adds to the acetylenic ester to give a Tebby zwitterion.…”

Section: Scheme 88 Synthesis Of New Derivatives Of Phenanthridinesmentioning

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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“…Yavari et al. described a multicomponent method to synthesize eight‐membered azaheterocycles, namely dialkyl(12 E ,14 E )‐7‐oxo‐10,11‐dihydro‐7 H ,9 H‐ azocino[2,1‐ a ]benzo[ de ]isoquinoline‐13,14‐dicarboxylates 390 through a 1,3‐dipolar cycloaddition reaction of dialkyl acetylenedicarboxylates 330 with in situ generated azomethine ylides from the reaction of prolines ( 205 and 218 ) and acenaphthylene‐1,2‐dione 389 (Scheme ) …”

Section: Decarboxylative Reactions Via Azomethine Ylides Pathwaymentioning

confidence: 99%

Recent Advances on Diverse Decarboxylative Reactions of Amino Acids

et al. 2019

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This review aims to report recent advances on decarboxylative reactions of amino acids catalyzed by transitionm etals or non-metals and the growing opportunities they present in the construction of complexc hemical scaffolds for applications encompassing natural product synthesis, synthetic methodology development, and functional materials. Different decarboxylative reactions have been highlighted such as radical, photoredox and metal and metal-free coupling reactions.e tc. Ther eview is divided into two main sections:o ne deals with reactions via radical pathways andt he other via azomethine ylide pathways.T he reactions have been discussed in more detail with particular emphasis on their useful applications andm echanistic illustrations.

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A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters

Cited by 10 publications

References 6 publications

Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin

Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin

Acetylenic Esters in Organic Synthesis

Recent Advances on Diverse Decarboxylative Reactions of Amino Acids

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