N,O-heterocyclics. 13. Isoxazolidinium salts as synthons to N,N, O-trisubstituted hydroxylamines

Substituted isoxazolidinium salts react with lithium aluminium hydride to yield open-ring products which have hydroxylamine structures. The bimolecular reaction-mechanism has been investigated by substituent effect and the structure of the products ascertained by spectroscopic methods with the aid of the MIKE technique. The overall process of the ring-opening substitution is controlled by the polarisation of the C? N bond with steric and conformational factors acting mainly at the C-5 position of the nucleus. The mechanism of isoxazolidinium ion reaction defines the use of these synthons towards the synthesis of N,N,O-trisubstituted hydroxylamines and substituted 1,3-amino-alcohols.     

N,N,N'-不同基团三取代乙二胺衍生物的简便合成

以2-取代咪唑啉为起始原料,经过磺酰化反应,得到磺酰基咪唑啉2a-2e,然后进行甲基化反应得到1,2,3-三取代咪唑啉碘盐3a-3e。化合物3在室温下经过水解反应或还原反应,可得到两类不同基团N,N,N'-三取代乙二胺衍生物4或5。该反应具有条件温和、副产物少、产物得率高和后处理简单等优点,提供了一种有效的三步合成不同基团N,N,N'-三取代乙二胺衍生物的新方法。所合成产物通过NMR、IR和元素分析方法进行了结构确证。     

peri-Naphthylenediamines. 37. Synthesis of N,N"-diisopropyl-N,N"-dimethyl-1,8-diaminonaphthalene

Alkylation of N,N"-dimethyl-1,8-diaminonaphthalene with 2-iodopropane in a KOH—DMSO system afforded a new proton sponge, viz., N,N"-diisopropyl-N,N"-dimethyl-1,8-diaminonaphthalene; the rotation barrier of the Prⁱ groups about the N—C bond is 68.4±0.4 kJ mol^–1 (DMSO).     

Review: Gaile,A.A., Proskuryakov,V.A., Semenov,L.V., Pul'tsin,N.M., Parizheva,N.V., Zakharov,A.P., Apter,Yu.M., and Solodova,N.I., Predel'nye koeffitsienty aktivnosti uglevodorodov: Spravochnik (Limiting Activity Coefficients of Hydrocarbons in Specific Solvents: A Handbook), Gaile,A.A., Ed.

Russian Journal of Applied Chemistry -     

Birthday of A.N. Smagunova

Chronicle

Birthday of A.N. Smagunova     

A Facile Synthesis of 1,4-Diketones from Organolithium Reagents and N,N,N′,N′-Tetramethylsuccinamide

The reaction of organolithium reagents (alkyl, aryl, heteroaryl) with N,N,N′,N′-tetramethylsuccinamide at 0 °C gives good yields of the corresponding 1,4-diketones.     

A new method of synthesis of N,N-dibenzyl-DL-phenylalanine and N,N-dibenzyl-DL-alanine

Russian Chemical Bulletin -     

N,N′-Bis(2-hydroxybenzyl)ethylenediamine-N,N′-dipropionic acid. A new chelating ligand for iron(III)

A new potentially chelating ligandN,N′-bis(2-hydroxybenzyl)ethylenediamine-N,N′-dipropionic acid, (HBEP) has been prepared in high yield and its ionization constants have been determined by potentiometric and spectrophotometric methods. The stability constant for the Fe^III-HBEP chelate has been determined spectrophotometrically, and the ligational behaviour of HBEP with iron(III) compared with that of its homologue, HBED (N,N′-bis(2-hydroxybenzyl)ethylenediamine-N,N′-diacetic acid). IPCL Communication No. 169.