Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group
Publication type: Journal Article
Publication date: 2016-06-03
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
27258556
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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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18
Total citations:
18
Citations from 2024:
1
(5%)
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GOST
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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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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.
Cite this
RIS
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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 -
Cite this
BibTex (up to 50 authors)
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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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MLA
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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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