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H-Bond-Assisted Intramolecular Nucleophilic Displacement of the 1-NMe(2) Group in 1,8-Bis(dimethylamino)naphthalenes as a Route to Multinuclear Heterocyclic Compounds and Strained Naphthalene Derivatives

  作者 POVALYAKHINA MARIA A; ANTONOV ALEXANDER S; DYABLO OLGA V; OZERYANSKII VALERY A; POZHARSKII ALEXANDER F  
  选自 期刊  Journal of Organic Chemistry;  卷期  2011年76-17;  页码  7157-7166  
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[摘要]It has been shown that azomethines, hydrazones, and mimes 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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