Department of Organic Chemistry, Southern Federal University, Zorge 7, 344090 Rostov-on-Don, Russian Federation.
J Org Chem. 2011 Sep 2;76(17):7157-66. doi: 10.1021/jo201171z. Epub 2011 Aug 11.
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.
已经证明，由 1,8-双（二甲基氨基）萘的 2(7)-羰基衍生物衍生的亚甲胺、腙和肟可以经历酸催化的杂环化反应，导致 1-NMe(2)基团的亲核取代。该过程被认为与底物的质子海绵性质直接相关，其中 1-NMe(2)作为一个较差的离去基团，通过形成螯合质子化形式初步被激活。已经以中等至高产率制备了许多难以获得的苯并[g]吲哚、苯并[g]喹唑啉、萘[2,1-d]异恶唑和 8-二甲基氨基-1-萘酚衍生物。
