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

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-NMe2 group. The process is believed to be directly connected with the pr...

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Published in:Journal of organic chemistry 2011-09, Vol.76 (17), p.7157-7166
Main Authors: Povalyakhina, Maria A, Antonov, Alexander S, Dyablo, Olga V, Ozeryanskii, Valery A, Pozharskii, Alexander F
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container_issue 17
container_start_page 7157
container_title Journal of organic chemistry
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creator Povalyakhina, Maria A
Antonov, Alexander S
Dyablo, Olga V
Ozeryanskii, Valery A
Pozharskii, Alexander F
description 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-NMe2 group. The process is believed to be directly connected with the proton sponge nature of the substrates, in which 1-NMe2, 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.
doi_str_mv 10.1021/jo201171z
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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
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