Formylation and acetylation of 2-ethoxynaphthalene with 1,3,5-triazines in polyphosphoric acid

Heating of 2-ethoxynaphthalene with 1,3,5-triazine or 2,4,6-trimethyl-1,3,5-triazine in polyphosphoric acid leads to the corresponding products of mono- or diacylation: 2-ethoxy-naphthalene-1-carbaldehyde, 1-acetyl-2-ethoxynaphthalene, 2-ethoxynaphthalene-1,8-dicarb-aldehyde, and 1,8-diacetyl-2-ethoxynaphthalene in ∼60–80% yield. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 207–208, January, 2008.     

Synthesis of 1,3-diazapyrenes and 1,3,7-triazapyrenes by the reaction of 1,8-naphthalenediamine with triazine in the presence of carbonyl compounds or benzonitrile in polyphosphoric acid

A novel three-component synthesis has been developed for 1,3-diazapyrenes based on the reaction of 1,8-naphthalenediamine with triazine and carbonyl compounds in polyphosphoric acid (PPA). The use of benzonitrile in place of the carbonyl compounds in this reaction gives 6-phenyl-1,3,7-triazapyrenes. Dedicated to one of the best Russian chemists A. F. Pozharskii on his 70th jubilee. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1694–1698, November, 2008.     

反相高效液相色谱法测定染料中间体1,8-二氨基萘

1 ,8 二氨基萘 ( 1 ,8 ｄｉａｍｉｎｏｎａｐｈｔｈａｌｅｎｅ)是一种常用试剂 ,主要作为中间体[1 ] 而用于一些染料的有机合成中。由于 1 ,8 二氨基萘应用极为广泛而配成溶液稳定性较差[2 ] ,给测定其含量带来了一定的困难 ,因此本文就如何在允许的条件下精密测定其含量的方法用高效液相的方法进行了研究 ,提出了一种用ＨＰＬＣ法测定工业产品中 1 ,8 二氨基萘的方法。1　实验部分1 1　仪器与试剂ＬＣ 6Ａ高效液相色谱仪 (日本岛津公司 ) ;Ｃ Ｒ3Ａ数据处理系统 ;ＳＰＤ 6ＡＶ紫外可见分光光度检测器。 1 ,8 二氨基萘标准品和工业产品 (…     

Reaction of vinylpyridines and vinylquinolines with 1,3,5-triazine in polyphosphoric acid

Russian Journal of Organic Chemistry -     

Self-condensation reaction of aromatic tetraamines in polyphosphoric acid

Ladder and partial ladder polymers have been obtained by self-condensation reactions of 1,2,4,5-tetraaminobenzene, 3,3′,4,4′-tetraaminodiphenyl ether, 3,3′-diaminobenzidine and 3,3′,4,4′-tetraaminodiphenyl sulfone in polyphosphoric acid. The products thus obtained are highly colored compounds with good thermal stability. They seem to be made up of polyquinoxaline or dihydrophenazine or a mixture of these two recurring units. They are slightly soluble in methanesulfonic acid and concentrated sulfuric acid and have inherent viscosities in the 0.2 to 0.4 range.     

A tandem decarboxylation and inverse electron-demand Diels-Alder reaction of amino-thiophenecarboxylic acids with 1,3,5-triazines

The scope of 1,3,5-triazine inverse electron-demand Diels-Alder (IDA) reactions was expanded to include aminothiophenecarboxylic acids as latent dienophiles. A series of 2-amino-3-thiophenecarboxylic acids (1a-d) and a 3-amino-2-thiophenecarboxylic acid (5) were introduced as productive dienophiles in IDA reactions with various 1,3,5-triazines (2a-e). This method is useful for the one-step synthesis of both thieno[2,3-d]pyrimidines and thieno[3,2-d]pyrimidines, which should complement existing methods.     

NMR spectra of 1,3,5-triazines with fluorinated substituents

The NMR spectra of a series of 1,3,5-triazines (1) in which one or more of the substituent groups are fluorinated are described, and the results are discussed in terms of bonding and geometry of the molecules. Remote effects of unsymmetrical substitution are observed in the fluorine-19 and carbon-13 spectra, in some molecules indicating restricted rotation about the bond joining an amino group to a ring carbon.     

Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid

In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.     

Nickel(II) and cobalt(II) chelates with products of condensation of 1,8-diaminonaphthalene and salycylaldehyde

Six Ni(II) and Co(II) chelates were synthesized from different reagents (Ni(II), Co(II) chlorides and 1,8-diaminonaphthalene or the products of a single or double condensation of the latter with salicylaldehyde) and identified and characterized by elemental analysis, powder X-ray diffraction, thermogravimetry, and conductivity methods. The ligand coordination mode and the spatial structure of the complexes were established from the magnetochemistry and spectroscopy (IR, diffuse reflection) data. The dimeric structure of one of the complexes formed due to the chloride bridges was confirmed by EXAFS method.