Synthesis of formyl derivatives of benzodiazacrown ethers and benzocryptands

Федорова, О. А.; Ведерников, А. И.; Baronova, I. E.; Eshcheulova, O. V.; Fedorchuk, E. A.; Gloe, Karsten; Gromov, S. P.

doi:10.1023/b:rucb.0000030817.96564.71

Cited by 6 publications

(3 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The main differ ence between this method and the method described earli er 31 is that the reaction is performed at room temperature (as opposed to the refluxing of the starting compounds in acetonitrile) and in a concentrated acetonitrile solution of the reactants (as opposed to the high dilution technique used in the method developed earlier 31 ). The formation of azamacrocyclic compounds can occur even in the absence of alkali carbonates, which has not been observed earlier in the syntheses of azacrown ethers.…”

mentioning

confidence: 98%

“…The physicochemical characteristics of form yl derivatives 3i-l have been described in our earlier study. 31 Compound 2a is diamine hydroiodide (see Fig. 1).…”

mentioning

confidence: 99%

“…Earlier, 31 we have developed a method for the synthe sis of formyl derivatives of benzodiazacrown ethers and benzocryptands based on the condensation of 3,4 bis(2 iodoethoxy)benzaldehyde with α,ω polyoxaalkanediamines and diazacrown ethers in the presence of alkali metal car bonates at high dilutions in different organic solvents and their mixtures with water. However, the reactions of un substituted terminal diamines with diazacrown ethers are accompanied by partial resinification of the starting reac tants and, consequently, the purification of the reaction products presents considerable difficulties.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of azacrown ethers and benzocryptands by macrocyclization of podands at high concentrations of reactants

et al. 2011

Self Cite

View full text Add to dashboard Cite

The reactions of 1,2 bis(2 Y ethoxy)benzenes, N,N bis(2 Y ethyl) N phenylamines, or 2,6 bis(Y methyl)pyridines (Y = I, Br, or OTs) with α,ω polyoxaalkanediamines or diazacrown ethers in the presence or absence of alkali carbonates in a concentrated acetonitrile solution of the reactants afforded the corresponding azacrown ethers or cryptands in high yields.The replacement of oxygen atoms in macroheterocy clic crown ether compounds by nitrogen atoms affords complexes capable of being coordinated to different types of metal cations (alkali, alkaline earth, heavy, and transi tion), 1-7 due to which this class of ligands has attracted interest. 8-12 Macrocyclic azapolyethers can be derivatized at the nitrogen atom, with the result that they can be used as intermediates in the synthesis of ion selective dyes, 13-17 biologically active compounds, 17-19 bicyclic analogs, and polymer bound reagents. 20,21There are various methods for the synthesis of azamac roheterocyclic compounds. 22-30 Nevertheless, the devel opment of new facile methods for the synthesis of ben zoazacrown compounds, particularly, of functionalized derivatives, is an important problem.Earlier, 31 we have developed a method for the synthe sis of formyl derivatives of benzodiazacrown ethers and benzocryptands based on the condensation of 3,4 bis(2 iodoethoxy)benzaldehyde with α,ω polyoxaalkanediamines and diazacrown ethers in the presence of alkali metal car bonates at high dilutions in different organic solvents and their mixtures with water. However, the reactions of un substituted terminal diamines with diazacrown ethers are accompanied by partial resinification of the starting reac tants and, consequently, the purification of the reaction products presents considerable difficulties.With the aim of preventing resinification and extend ing the range of the reactants, in the present study we developed a procedure for the synthesis of derivatives of benzoazacrown compounds by the condensation of acy clic precursors under mild conditions. The main differ ence between this method and the method described earli er 31 is that the reaction is performed at room temperature (as opposed to the refluxing of the starting compounds in acetonitrile) and in a concentrated acetonitrile solution of the reactants (as opposed to the high dilution technique used in the method developed earlier 31 ). The formation of azamacrocyclic compounds can occur even in the absence of alkali carbonates, which has not been observed earlier in the syntheses of azacrown ethers. The advantages of the new method are that the reaction products are formed in good or high yields and are characterized by higher purity.We studied the condensation of substituted 1,2 bis (2 iodoethoxy)benzenes 1a,b and related dielectrophiles de signed on diethylphenylamine 1c,d and 2,6 lutidine 1e,f with diamines 2a-f and diazacrown ethers 2g,h and 3d in the presence of alkali carbonates (Scheme 1).The condensation occurs with linear dielectrophiles 1a-f and dinucleophiles 2a-h or 3d in a concentrated acetonit...

show abstract

mentioning

confidence: 98%

“…The physicochemical characteristics of form yl derivatives 3i-l have been described in our earlier study. 31 Compound 2a is diamine hydroiodide (see Fig. 1).…”

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of azacrown ethers and benzocryptands by macrocyclization of podands at high concentrations of reactants

et al. 2011

Self Cite

View full text Add to dashboard Cite

show abstract

Synthesis of Formyl Derivatives of Benzodiazacrown Ethers and Benzocryptands.

et al. 2004

View full text Add to dashboard Cite

Synthesis of Formyl Derivatives of Benzodiazacrown Ethers and Benzocryptands. -Several benzodiazacrown ethers and benzocryptands, e.g. compound (III), are prepared by condensation of diiodide (I) with α,ω-oligooxaalkanediamines or diazacrown ethers under high-dilution conditions in the presence of alkali metal carbonates. The influence of the solvent and of alkali metal carbonates on the course of the reaction is investigated. -(FEDOROVA*, O. A.; VEDERNIKOV, A. I.; BARONOVA, I. E.; ESHCHEULOVA, O. V.; FEDORCHUK, E. A.; GLOE, K.; GROMOV, S. P.; Russ.

show abstract