Nitration of Pyrrolo[2,1-a]isoquinolines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4649 - 4661

Опубликована: Март 22, 2023

We have successfully modified a series of pyrrolo[2,1-a]isoquinolines via direct nitration under mild reaction conditions. Easily accessible nitrates including CAN, Cu(NO3)2·H2O, and Fe(NO3)3·9H2O all can serve as effective nitrating reagents for functionalizing pyrrolo[2,1-a]isoquinolines. Various nitro-bearing been efficiently prepared in acceptable to good yields.

Язык: Английский

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Organocatalytic regio- and enantioselective C1-arylation of β,γ-alkynyl-α-imino esters with pyrrolo[2,1-a]isoquinolines

Chemical Communications, Год журнала: 2023, Номер 60(7), С. 831 - 834

Опубликована: Дек. 15, 2023

We herein report regio- and enantioselective arylation of β,γ-alkynyl-α-imino esters with pyrroloisoquinolines. Using chiral phosphoric acid catalysts, a wide range novel axially tetrasubstituted α-amino allenoates were accessed in good yields excellent enantioselectivities. Notably, this transformation occurred preferentially at the sterically more hindered C1-position The potential scalability late-stage functionalization demonstrated utility current protocol.

Язык: Английский

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Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 9816 - 9829

Опубликована: Июнь 25, 2024

Various substituted pyrrolo[1,2-

Язык: Английский

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Synthesis of Furan-Containing Pyrrolo[2,1-a]Isoquinoline Derivatives Based on Phosphoranylidenesucciminide

Chemistry of Natural Compounds, Год журнала: 2025, Номер unknown

Опубликована: Март 26, 2025

Язык: Английский

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Oxidative Iodination of Pyrrolo[2,1-a]isoquinolines with NaI/mCPBA

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 4, 2025

A mild late-stage modification of pyrrolo[2,1-a]isoquinoline derivatives has been achieved through oxidative iodination with NaI as the iodine source and mCPBA oxidant. series pyrrolo[2,1-a]isoquinolines iodinated readily at ambient temperature in moderate to excellent yield (40→99% yields). Other heteroarenes great importance such substituted pyrroles indoles could also be compatible this process. It was found that combination HI can alternatively employed for efficient efficiently.

Язык: Английский

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AcBr/DMSO Mediated Sulfenylation of Pyrrolo[2,1-a]isoquinolines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7347 - 7361

Опубликована: Май 11, 2023

We have developed a mild sulfenylation of pyrrolo[2,1-a]isoquinolines with acetyl bromide and dimethyl sulfoxide. A wide range functionalized could be prepared efficiently through the formation C-S bond thiophenols (27 examples, 36-94% yields). The current strategy can also utilized for functionalization pyrrolo[1,2-a]quinolines indole.

Язык: Английский

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POCl₃/Sulfoxide and AcCl/Sulfoxide Mediated Chlorination of Pyrrolo[2,1-a]isoquinolines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11935 - 11944

Опубликована: Авг. 7, 2023

We have developed an efficient chlorination of pyrrolo[2,1-a]isoquinoline derivatives using POCl3 as the chlorine source and tetramethylene sulfoxide a promoter. A series pyrrolo[2,1-a]isoquinolines, polysubstituted pyrroles, naphthols been readily chlorinated under mild reaction conditions (26 examples, up to >99% yield). AcCl can also act competently in this reaction.

Язык: Английский

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Visible-light-induced C(sp³)–H bromination of 4-methylthiophene derivatives with HBr/H₂O₂

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(20), С. 4145 - 4152

Опубликована: Янв. 1, 2024

A convenient method to synthesize ethyl 4-(bromomethyl)thiophene-3-carboxylate derivatives has been developed

Язык: Английский

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Iron-Catalyzed Synthesis of Peroxylpyrrolo[2,1-a]isoquinolines through Oxidative Dearomatization

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15326 - 15334

Опубликована: Окт. 25, 2023

A mild late-stage modification of pyrrolo[2,1-a]isoquinolines was established through iron-catalyzed oxidative dearomatization and peroxidation. Peroxylated pyrroloisoquinolines have been prepared readily with hydroperoxide in low to good yields (up 72%) at room temperature. Interestingly, the treatment fully aromatized pyrrolo[1,2-a]quinolines under current reaction system resulted formation ring-opening products.

Язык: Английский

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POCl₃/Sulfoxide-Promoted Synthesis of Indolizino[8,7-b]indoles

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16400 - 16409

Опубликована: Ноя. 20, 2023

A mild chlorocyclization of pyrrole-tethered indoles has been realized using POCl3 as the chlorine source and tetramethylene sulfoxide promoter. variety chlorinated indolizino[8,7-b]indole derivatives have constructed efficiently under this reaction system in moderate to good yields (19 examples, up 93% yield).

Язык: Английский

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