A Diels–Alder/Ene Cascade Leading to 5‐(Pyrrolidin‐3‐yl)thieno[3,2‐<i>e</i>]isoindoles from Ketone‐derived 2‐Vinylthiophenes and <i>N</i>‐Phenylmaleimide

Noland, Wayl­and E.; Huisenga, Matthew P.; Herzig, Ryan J.; Rosenow, John; Kim, Hoyeon; Kroll, Neil J.; Nesmelov, A. L.; Johnson, Benjamin T.; Duncan, Nathan S.; Ratanayanon, Jidapa; Yue, Ruixian A.; Xiong, Kenny; Ong, Bee K.; Vo, Diane; Klein, Nathan; Lang, Simon B.; Riley, Jacob K.; Daniels, Steven P.; Tritch, Kenneth J.

doi:10.1002/jhet.3327

Cited by 2 publications

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“…Interestingly, a few reports were found on the Diels–Alder reaction of 2-(1′-cycloalkenyl)thiophenes or 2-(1′-cycloalkenyl)benzo[ b ]thiophenes ( 10 , Figure ). The resulting Diels–Alder adducts can also undergo Michael-addition or ene-reaction with an additional molecule of dienophile. ,, In an extension of our prior works with 3-vinylindoles, 2- and 3-vinylpyrroles, and 5-(pyrrolidin-3-yl)thieno[3,2- e ]isoindoles ( 8 and 9 ; Figure ), we became interested in the Diels–Alder reaction of 2-(1′-cycloalkenyl)thiophenes and 2-(1′-cycloalkenyl)benzo[ b ]thiophenes with N -phenylmaleimide as the dienophile in the current study. In this article, we focused on understanding the reactivity of 2-(1′-cycloalkenyl)thiophenes and 2-(1′-cycloalkenyl)benzo[ b ]thiophenes dienes in the Diels–Alder/ene reactions and also detailed characterization of the stereochemistry of the products.…”

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confidence: 99%

Diels–Alder/Ene Reactivities of 2-(1′-Cycloalkenyl)thiophenes and 2-(1′-Cycloalkenyl)benzo[b]thiophenes with N-Phenylmaleimides: Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene Product Distributions

et al. 2020

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Scaffolds of thiophene and benzothiophene are the important class of bioactive compounds found abundant in nature. The Diels–Alder reactions of 2-(1′-cycloalkenyl)thiophenes and 2-(1′-cycloalkenyl)benzo[b]thiophenes having the alkene groups present in five-, six-, seven-, eight-, and twelve-membered rings with substituted N-phenylmaleimides are characterized. The size of the cycloalkene rings plays a critical role in dictating the product distributions of expected and isomerized Diels–Alder adducts. 2D NMR studies indicate that the isolated isomers for 2-(1′-cycloalkenyl)thiophenes having five-, six-, and seven-membered rings are aromatized benzothiophene products, whereas eight- and twelve-membered rings are un-rearranged adducts. In addition, the product of subsequent ene-reaction with the N-phenylmaleimide is isolated for the five- and six-membered ring cases. Interestingly, in the 2-(1′-cycloalkenyl)benzo[b]thiophene having five-, six-, seven-, eight-, and twelve-membered rings, the un-rearranged dibenzothiophene Diels–Alder adduct is isolated in every instance. Molecular mechanics and density functional theory (M06-2X and PBE0-D3) calculations are performed to understand the differential reactivity of the various dienes for both the initial Diels–Alder reaction and a possible, subsequent ene reaction.

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Section: Introductionmentioning

confidence: 99%

Diels–Alder/Ene Reactivities of 2-(1′-Cycloalkenyl)thiophenes and 2-(1′-Cycloalkenyl)benzo[b]thiophenes with N-Phenylmaleimides: Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene Product Distributions

et al. 2020

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A Highly Selective Synthesis of (E)‐11‐Arylidenebenzo [4′,5′] thieno [2′,3′ : 4,5] Pyrimido [2,1‐a] Isoindol‐13(1H)‐ones via Copper‐Catalyzed Sonogashira Coupling and Hydroamination

He,

Wang,

Zhang

et al. 2024

Asian J Org Chem

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An efficient and highly selective reaction of 2‐(2‐bromophenyl)‐5,6,7,8‐tetrahydrobenzo[4,5]thieno[2,3‐d]pyrimidin‐4(3H)‐one and terminal alkyne has been developed under palladium‐free conditions by CuI‐catalyzed sequential Sonogashira coupling reaction and 5‐exo‐dig hydroamination reaction. A series of 11‐arylidene‐2,3,4,11‐tetrahydrobenzo[4',5']thieno[2',3':4,5]pyrimido[2,1‐a]isoindol‐13(1H)‐one derivatives with only the (E)‐configuration were obtained and stabilized by intramolecular C‐H…O hydrogen bonding for stabilization.

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A Diels–Alder/Ene Cascade Leading to 5‐(Pyrrolidin‐3‐yl)thieno[3,2‐e]isoindoles from Ketone‐derived 2‐Vinylthiophenes and N‐Phenylmaleimide

Cited by 2 publications

References 45 publications

Diels–Alder/Ene Reactivities of 2-(1′-Cycloalkenyl)thiophenes and 2-(1′-Cycloalkenyl)benzo[b]thiophenes with N-Phenylmaleimides: Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene Product Distributions

Diels–Alder/Ene Reactivities of 2-(1′-Cycloalkenyl)thiophenes and 2-(1′-Cycloalkenyl)benzo[b]thiophenes with N-Phenylmaleimides: Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene Product Distributions

A Highly Selective Synthesis of (E)‐11‐Arylidenebenzo [4′,5′] thieno [2′,3′ : 4,5] Pyrimido [2,1‐a] Isoindol‐13(1H)‐ones via Copper‐Catalyzed Sonogashira Coupling and Hydroamination

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