Organic Letters

, том 18 , издание 12 , страницы 2872-2875

Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe₂ Group

Тип публикации: Journal Article

Дата публикации: 2016-06-03

American Chemical Society (ACS)

Organic Letters

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CiteScore: 7.7

Impact factor: 4.7

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.6b01178

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PubMed ID: 27258556

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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It has been found that 2-bromo-1,8-bis(dimethylamino)naphthalene on sequential treatment with n-BuLi and 2 equiv of the same or different aryl(hetaryl) cyanide as a result of [2 + 2 + 2] nucleophilic cascade annulation produces 10-dimethylaminobenzo[h]quinazolines, as yet unknown NMe2/-N═ analogues of the proton sponge. It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe2 groups furnishing quinazolino[7,8-h]quinazoline derivatives is also possible. The process is remarkable by surprisingly mild nucleophilic displacement of an unactivated aromatic NMe2 group.

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Mikshiev V. Y., Antonov A. S., Pozharskii A. F. Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group // Organic Letters. 2016. Vol. 18. No. 12. pp. 2872-2875.

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TY - JOUR

DO - 10.1021/acs.orglett.6b01178

UR - https://doi.org/10.1021/acs.orglett.6b01178

TI - Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group

T2 - Organic Letters

AU - Mikshiev, Vladimir Y

AU - Antonov, Alexander S.

AU - Pozharskii, Alexander F.

PY - 2016

DA - 2016/06/03

PB - American Chemical Society (ACS)

SP - 2872-2875

IS - 12

VL - 18

PMID - 27258556

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2016_Mikshiev,

author = {Vladimir Y Mikshiev and Alexander S. Antonov and Alexander F. Pozharskii},

title = {Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group},

journal = {Organic Letters},

year = {2016},

volume = {18},

publisher = {American Chemical Society (ACS)},

month = {jun},

url = {https://doi.org/10.1021/acs.orglett.6b01178},

number = {12},

pages = {2872--2875},

doi = {10.1021/acs.orglett.6b01178}

}

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Mikshiev, Vladimir Y., et al. “Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group.” Organic Letters, vol. 18, no. 12, Jun. 2016, pp. 2872-2875. https://doi.org/10.1021/acs.orglett.6b01178.

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Organic Letters

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