Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles

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Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles. / Капланский, Марк Валерьевич ; Антонов, Александр Сергеевич ; Цыбулин, Семен Валерьевич.

в: Chemistry - A European Journal, Том 30, № 10, e202303768, 23.01.2024.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{c623e26c40e04a2491e0d26737f6259d,

title = "Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles",

abstract = "A simple and effective organolithium approach to the synthesis of 2-substituted benzo[cd]indoles from peri-dihalonaphthalenes and nitriles has been developed. The reaction proceeds via a surprisingly easy intramolecular aromatic nucleophilic substitution facilitated by the “clothespin effect”. The discovered transformation provides good isolated yields, allows usage of an extensive range of nitriles, and demonstrates a good substituents tolerance. UV-absorption and NMR spectra of the obtained benzo[cd]indoles and their protonated forms demonstrated exclusive protonation to the indole nitrogen atom even in the presence of two NMe2 groups in positions 5 and 6 (i. e. “proton sponge” moiety).",

keywords = "heterocycles, indoles, naphthalene, nucleophilic substitution, organolithiums",

author = "Капланский, {Марк Валерьевич} and Антонов, {Александр Сергеевич} and Цыбулин, {Семен Валерьевич}",

year = "2024",

month = jan,

day = "23",

doi = "10.1002/chem.202303768",

language = "English",

volume = "30",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-Blackwell",

number = "10",

}

RIS

TY - JOUR

T1 - Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles

AU - Капланский, Марк Валерьевич

AU - Антонов, Александр Сергеевич

AU - Цыбулин, Семен Валерьевич

PY - 2024/1/23

Y1 - 2024/1/23

N2 - A simple and effective organolithium approach to the synthesis of 2-substituted benzo[cd]indoles from peri-dihalonaphthalenes and nitriles has been developed. The reaction proceeds via a surprisingly easy intramolecular aromatic nucleophilic substitution facilitated by the “clothespin effect”. The discovered transformation provides good isolated yields, allows usage of an extensive range of nitriles, and demonstrates a good substituents tolerance. UV-absorption and NMR spectra of the obtained benzo[cd]indoles and their protonated forms demonstrated exclusive protonation to the indole nitrogen atom even in the presence of two NMe2 groups in positions 5 and 6 (i. e. “proton sponge” moiety).

AB - A simple and effective organolithium approach to the synthesis of 2-substituted benzo[cd]indoles from peri-dihalonaphthalenes and nitriles has been developed. The reaction proceeds via a surprisingly easy intramolecular aromatic nucleophilic substitution facilitated by the “clothespin effect”. The discovered transformation provides good isolated yields, allows usage of an extensive range of nitriles, and demonstrates a good substituents tolerance. UV-absorption and NMR spectra of the obtained benzo[cd]indoles and their protonated forms demonstrated exclusive protonation to the indole nitrogen atom even in the presence of two NMe2 groups in positions 5 and 6 (i. e. “proton sponge” moiety).

KW - heterocycles

KW - indoles

KW - naphthalene

KW - nucleophilic substitution

KW - organolithiums

UR - https://www.mendeley.com/catalogue/0b1249a4-0fc2-3dce-b62e-31842764ca69/

U2 - 10.1002/chem.202303768

DO - 10.1002/chem.202303768

M3 - Article

VL - 30

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 10

M1 - e202303768

ER -

ID: 115680061