N,N,N′-trialkyl-1,8-diaminonaphthalenes:: convenient method of preparation from protonated proton sponges and the first X-ray information

被引：28

作者：

Ozeryanskii, VA

Pozharskii, AF

Koroleva, MG

Shevchuk, DA

Kazheva, ON

Chekhlov, AN

Shilov, GV

Dyachenko, OA

机构：

[1] Rostov State Univ, Dept Organ Chem, Rostov Na Donu 344090, Russia

[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Moscow Region, Russia

来源：

TETRAHEDRON | 2005年 / 61卷 / 17期

基金：

俄罗斯基础研究基金会;

关键词：

proton sponges; N,N,N '-trialkyl-1,8-diaminonaphthalenes; demethylation; dealkylation; realkylation; intramolecular hydrogen bond; nitronaphthalenes; molecular and crystal structures;

D O I：

10.1016/j.tet.2005.02.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple procedure for the synthesis of N,N,N'-trialkyl-1,8-diaminonaphthalenes is described. It consists in partial demethylation (dealkylation) of commercially available proton sponge [1,8-bis(dimethylamino)naphthalene] and some of its derivatives at heating with HBr-KI-DMF system. Limitation, scope and a possible mechanistic pathway for the reaction are discussed. For isomeric 8-dimethylamino-1-methylamino- and 1-dimethylamino-8-methylamino-4-nitronaphthalenes, X-ray measurements have been conducted. The first examples of complete realkylation reactions in the naphthalene proton sponges are reported. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4221 / 4232

页数：12

共 44 条

[21] peri-naphthylenediamines.: 28.: Nitration of 1,8-bis(dimethylamino)naphthalene and 5,6-bis(dimethylamino)acenaphthene in neutral and weakly acidic media.: The first case of isolation of o-nitro and o,o′-dinitro derivatives of "proton sponges" [J].