H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives.
Publication type: Journal Article
Publication date: 2011-08-11
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
21834514
Organic Chemistry
Abstract
It has been shown that azomethines, hydrazones, and oximes derived from 2(7)-carbonyl derivatives of 1,8-bis(dimethylamino)naphthalene can undergo acid-catalyzed heterocyclization leading to a nucleophilic displacement of the 1-NMe(2) group. The process is believed to be directly connected with the proton sponge nature of the substrates, in which 1-NMe(2), being a poor leaving group, is preliminary activated via the formation of a chelated protonated form. A number of difficult to access derivatives of benzo[g]indazole, benzo[g]quinazoline, naphtho[2,1-d]isoxazole, and 8-dimethylamino-1-naphthol have been prepared in moderate to high yields.
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GOST
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Povalyakhina M. A. et al. H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives. // Journal of Organic Chemistry. 2011. Vol. 76. No. 17. pp. 7157-7166.
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Povalyakhina M. A., Antonov A. S., Dyablo O. V., Ozeryanskii V. A., Pozharskii A. F. H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives. // Journal of Organic Chemistry. 2011. Vol. 76. No. 17. pp. 7157-7166.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo201171z
UR - https://doi.org/10.1021/jo201171z
TI - H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives.
T2 - Journal of Organic Chemistry
AU - Povalyakhina, Maria A
AU - Antonov, Alexander S.
AU - Dyablo, Olga V.
AU - Ozeryanskii, Valery A.
AU - Pozharskii, Alexander F.
PY - 2011
DA - 2011/08/11
PB - American Chemical Society (ACS)
SP - 7157-7166
IS - 17
VL - 76
PMID - 21834514
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2011_Povalyakhina,
author = {Maria A Povalyakhina and Alexander S. Antonov and Olga V. Dyablo and Valery A. Ozeryanskii and Alexander F. Pozharskii},
title = {H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives.},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/jo201171z},
number = {17},
pages = {7157--7166},
doi = {10.1021/jo201171z}
}
Cite this
MLA
Copy
Povalyakhina, Maria A., et al. “H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives..” Journal of Organic Chemistry, vol. 76, no. 17, Aug. 2011, pp. 7157-7166. https://doi.org/10.1021/jo201171z.
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