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Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums. / Толоченко, Дмитрий Олегович; Цыбулин, Семен Валерьевич; Якубенко, Артем Алексеевич; Тупикина, Елена Юрьевна; Антонов, Александр Сергеевич.

In: Organic Letters, Vol. 25, No. 6, 17.02.2023, p. 977-981.

Research output: Contribution to journal › Article › peer-review

Harvard

Толоченко, ДО, Цыбулин, СВ, Якубенко, АА, Тупикина, ЕЮ & Антонов, АС 2023, 'Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums', Organic Letters, vol. 25, no. 6, pp. 977-981. https://doi.org/10.1021/acs.orglett.3c00035

APA

Толоченко, Д. О., Цыбулин, С. В., Якубенко, А. А., Тупикина, Е. Ю., & Антонов, А. С. (2023). Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums. Organic Letters, 25(6), 977-981. https://doi.org/10.1021/acs.orglett.3c00035

Vancouver

Толоченко ДО, Цыбулин СВ, Якубенко АА, Тупикина ЕЮ, Антонов АС. Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums. Organic Letters. 2023 Feb 17;25(6):977-981. https://doi.org/10.1021/acs.orglett.3c00035

Author

Толоченко, Дмитрий Олегович ; Цыбулин, Семен Валерьевич ; Якубенко, Артем Алексеевич ; Тупикина, Елена Юрьевна ; Антонов, Александр Сергеевич. / Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums. In: Organic Letters. 2023 ; Vol. 25, No. 6. pp. 977-981.

BibTeX

@article{21a3c22ebf4d40e8895f0694004978b9,
title = "Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums",
abstract = "The interaction of peri-dilithionaphthalenes with organic cyanides was studied. Instead of the expected peri-diimines, the reaction leads to the formation of three types of benzo[ de]isoquinolines. Treatment of unsubstituted 1,8-dilithionaphthalene with aromatic nitriles results in the formation of 1-amino-1,3-diaryl-1 H-benzo[ de]isoquinolines. In contrast, 4,5-dilithio-1,8-bis(dimethylamino)naphthalene gives an aromatic isoquinolonium cation via elimination of ammonia under the same condition. Upon treatment with tert-butylcyanide, both dilithionaphthalenes undergo a transformation to 1-amino-3,4-di- tert-butyl-4 H-benzo[ de]isoquinolines. The observed reactivity was supported by quantum chemical calculations. ",
author = "Толоченко, {Дмитрий Олегович} and Цыбулин, {Семен Валерьевич} and Якубенко, {Артем Алексеевич} and Тупикина, {Елена Юрьевна} and Антонов, {Александр Сергеевич}",
year = "2023",
month = feb,
day = "17",
doi = "10.1021/acs.orglett.3c00035",
language = "English",
volume = "25",
pages = "977--981",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "6",

}

RIS

TY - JOUR

T1 - Spontaneous Cyclization of peri-Diiminonaphthalenes Leading to the Formation of Benzo[de]isoquinolines and Stable Benzo[de]isoquinoliniums

AU - Толоченко, Дмитрий Олегович

AU - Цыбулин, Семен Валерьевич

AU - Якубенко, Артем Алексеевич

AU - Тупикина, Елена Юрьевна

AU - Антонов, Александр Сергеевич

PY - 2023/2/17

Y1 - 2023/2/17

N2 - The interaction of peri-dilithionaphthalenes with organic cyanides was studied. Instead of the expected peri-diimines, the reaction leads to the formation of three types of benzo[ de]isoquinolines. Treatment of unsubstituted 1,8-dilithionaphthalene with aromatic nitriles results in the formation of 1-amino-1,3-diaryl-1 H-benzo[ de]isoquinolines. In contrast, 4,5-dilithio-1,8-bis(dimethylamino)naphthalene gives an aromatic isoquinolonium cation via elimination of ammonia under the same condition. Upon treatment with tert-butylcyanide, both dilithionaphthalenes undergo a transformation to 1-amino-3,4-di- tert-butyl-4 H-benzo[ de]isoquinolines. The observed reactivity was supported by quantum chemical calculations.

AB - The interaction of peri-dilithionaphthalenes with organic cyanides was studied. Instead of the expected peri-diimines, the reaction leads to the formation of three types of benzo[ de]isoquinolines. Treatment of unsubstituted 1,8-dilithionaphthalene with aromatic nitriles results in the formation of 1-amino-1,3-diaryl-1 H-benzo[ de]isoquinolines. In contrast, 4,5-dilithio-1,8-bis(dimethylamino)naphthalene gives an aromatic isoquinolonium cation via elimination of ammonia under the same condition. Upon treatment with tert-butylcyanide, both dilithionaphthalenes undergo a transformation to 1-amino-3,4-di- tert-butyl-4 H-benzo[ de]isoquinolines. The observed reactivity was supported by quantum chemical calculations.

UR - https://www.mendeley.com/catalogue/3b76d535-e05c-3517-a371-614a15500ace/

U2 - 10.1021/acs.orglett.3c00035

DO - 10.1021/acs.orglett.3c00035

M3 - Article

C2 - 36748976

VL - 25

SP - 977

EP - 981

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 6

ER -

ID: 105207153