Synthesis of macroheterocycles ? Analogs of dibenzo-crown compounds. 18-Membered dioxadiaza-crown compounds

Formanovskii, A. A.; Михура, И. В.; Sokolovskii, S. A.; Murakhovskaya, A. S.; Терентьев, П. Б.; Sharbatyan, P. A.

doi:10.1007/bf00479353

Cited by 4 publications

(5 citation statements)

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“…11,12,14 The chemical shifts and peak assignments given in Table 5 agree most closely with those in d 6 -DMSO reported by Markovich et al 14 and in CDCl 3 by Formanovskii et al 11 However, H3-H5 were not assigned by the latter authors, and the chemical shift for the amide proton (8.08 ppm) they reported 11 differs significantly from that reported here (8.73 ppm) and by others (8.75-9.00 ppm). 10,13,14 The value for H2 given in Table 5 (8.22 ppm) falls in the range (7.9-8.30 ppm) reported by other groups.…”

Section: Resultsmentioning

confidence: 97%

“…There is little variation of the 1 H and 13 C chemical shifts for comparable nuclei among the three compounds, and the 13 C chemical shifts for various nuclei occur in the expected regions. 11,19 For compound 2, an earlier report proposed that proton signals observed at 8.5 ppm and 9.2 ppm could be attributed to contributions from the lactim (O-H) and lactam (N-H) tautomers, respectively. 9 However, the present study shows that the signals in this region can be assigned to the ortho aromatic proton (H2) and the amide proton.…”

Section: Resultsmentioning

confidence: 97%

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¹H and ¹³C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

Smith

Alguindigue

Khan

et al. 2006

Magnetic Reson in Chemistry

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Three monocyclic polyether dilactams, 17,18-dihydro-5H, 9H-dibenzo[e,n]1,4,10,7,13trioxadiazacyclopentadecine-6,10(7H,11H)-dione (1); 9,10,20,21-tetrahydro-5H, 12H-dibenzo[e,q]1,4,10,13,7,16tetraoxadiazacyclooctadecine-6, 13(7H,14H)-dione (2); and 6,7,9,10-tetrahydro-16H, 20H-dibenzo[h,q]1,4,7,13, 10,16tetraoxadiazacyclooctadecine-17, 21(18H,22H)-dione (3) were isolated during the synthesis of several benzoannelated cryptands. The complete assignments of the 1H and 13C NMR spectra of 1, 2 and 3 in CDCl3 were made using gCOSY, gHMBC, gHMQC, HMQC, HSQC, and NOESY 1D techniques. The ortho (H2) benzene protons show significant downfield shifts (1.16-1.43 ppm) that are consistent with an exodentate orientation for the amide carbonyl groups. The X-ray crystal structures of 1, 2 and 3 show that the carbonyl groups adopt an exodentate conformation in the solid state.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 97%

¹H and ¹³C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

Smith

Alguindigue

Khan

et al. 2006

Magnetic Reson in Chemistry

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“…12 1,2 Bis[2 (3 pyridylmethylideneamino)phenylthio]ethane (1). 3 Pyridinecarboxaldehyde (0.45 mL, 0.40 g, 3.60 mmol) was added to a solution of 1,2 bis(2 aminophenylthio)ethane (0.50 g, 1.80 mmol) in EtOH (50 mL).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and electrochemical characterization of complexes of 1,2-bis[2-(pyridylmethylideneamino)phenylthio]ethanes with transition metals (CoII, NiII, CuII)

et al. 2008

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Transition metal (Ni II , Co II , and Cu II ) complexes with 1,2 bis[2 (3 pyridylmethylidene amino)phenylthio]ethane (1) and 1,2 bis[2 (4 pyridylmethylideneamino)phenylthio]ethane (2) were synthesized for the first time by slow diffusion of solutions of compounds 1 or 2 in CH 2 Cl 2 into solutions of MХ 2 •nH 2 O (M = Ni, Co, or Cu; X = Cl or NO 3 ; n = 2 or 6) in ethanol. The reactions with Co II and Cu II chlorides afford complexes of composition M(L)Cl 2 (L = 1 or 2). The reactions of compound 1 with Ni II salts produce complexes with 1,2 bis(2 aminophenylthio)ethane. The molecular structure of dinitrato[1,2 bis(2 amino phenylthio)ethane]nickel(II) was confirmed by X ray diffraction. The ligands and the com plexes were investigated by cyclic voltammetry and rotating disk electrode voltammetry. The initial reduction of the complexes proceeds at the metal atom. The oxidation of the chlorine containing complexes proceeds at the coordinated chloride anion.Transition metal complexes, in particular, nickel(II), 1 cobalt(II), 2 and copper(II) 3 complexes, with organic S,N containing ligands have attracted attention as models of metalloenzymes and electroactive catalysts. Thio substi tuted imines are among promising organic ligands. Previ ously, 4 we have synthesized a series of acyclic and macro cyclic S,S alkylidenethiosalicylimines. Some of these compounds are electrochemically reversibly reduced and are potential catalysts for electrochemically induced alkylation reactions. It was found that complexes with acyclic tetradentate N 2 S 2 ligands containing two imine groups are most often able to undergo reversible reduc tion and, consequently, these complexes are most suitable for further investigation as such catalysts. In the present study, we investigated the complexation in the 1,2 bis[2 (pyridylmethylideneamino)phenylthio] ethane-MX 2 system (M = Ni, Co, or Cu; X = Cl or NO 3 ) and the electrochemical behavior of the resulting complexes. Results and DiscussionSynthesis of ligands and complexes. Ligands 1 and 2 were synthesized by the reaction of 1,2 bis(2 amino phenylthio)ethane with 3 or 4 pyridinecarboxaldehyde, respectively (Scheme 1). Scheme 1Py = 3 pyridyl (1), 4 pyridyl (2) Complexes with metal chlorides were synthesized by slow diffusion of compounds 1 or 2 dissolved in CH 2 Cl 2 into solutions of MCl 2 •nH 2 O (M = Ni, Co, or Cu) in ethanol or acetonitrile (Scheme 2). As a result, we ob tained (for ligand 2, in all cases; for ligand 1, in the reactions with Co II and Cu II salts) powdered complexes of composition M(L)Cl 2 (L = 1 or 2), as determined by elemental analysis.Imino sulfides 1 and 2 can act as tetradentate ligands coordinated to the metal ion through the N 2 S 2 system to

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“…The 18-membered benzoannelated monocyclic diamine was prepared according to reported methods (Lockhart & Thompson, 1977;Formanovskii et al, 1988). The tricyclic tetralactam precursor of (I) was obtained as the 2 + 2 cycloaddition product from the reaction of the monocyclic diamine (0.0105 M) in toluene-DMF (5:3) and 2,2 0oxydiacetyl chloride (0.0110 M) in toluene.…”

Section: Methodsmentioning

confidence: 99%

6,7,9,10,17,18,20,21,28,29,31,32,39,40,42,43-Hexadecahydro-16,44:22,38-di(ethanooxyethano)-5,8,11,19,27,30,33,41-octaoxa-16,22,38,44-tetraazatetrabenzo[h,q,z,i ₁]cyclohexatriacontine: a benzoannelated tricyclic cryptand

Smith¹,

Rocher²,

Powell³

et al. 2007

Acta Cryst E

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Synthesis of macroheterocycles ? Analogs of dibenzo-crown compounds. 18-Membered dioxadiaza-crown compounds

Cited by 4 publications

References 4 publications

¹H and ¹³C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

¹H and ¹³C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

Synthesis and electrochemical characterization of complexes of 1,2-bis[2-(pyridylmethylideneamino)phenylthio]ethanes with transition metals (CoII, NiII, CuII)

6,7,9,10,17,18,20,21,28,29,31,32,39,40,42,43-Hexadecahydro-16,44:22,38-di(ethanooxyethano)-5,8,11,19,27,30,33,41-octaoxa-16,22,38,44-tetraazatetrabenzo[h,q,z,i ₁]cyclohexatriacontine: a benzoannelated tricyclic cryptand

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Synthesis of macroheterocycles ? Analogs of dibenzo-crown compounds. 18-Membered dioxadiaza-crown compounds

Cited by 4 publications

References 4 publications

1H and 13C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

1H and 13C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

Synthesis and electrochemical characterization of complexes of 1,2-bis[2-(pyridylmethylideneamino)phenylthio]ethanes with transition metals (CoII, NiII, CuII)

6,7,9,10,17,18,20,21,28,29,31,32,39,40,42,43-Hexadecahydro-16,44:22,38-di(ethanooxyethano)-5,8,11,19,27,30,33,41-octaoxa-16,22,38,44-tetraazatetrabenzo[h,q,z,i 1]cyclohexatriacontine: a benzoannelated tricyclic cryptand

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¹H and ¹³C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

¹H and ¹³C NMR assignments and X‐ray structures for three monocyclic benzoannelated dilactam polyethers

6,7,9,10,17,18,20,21,28,29,31,32,39,40,42,43-Hexadecahydro-16,44:22,38-di(ethanooxyethano)-5,8,11,19,27,30,33,41-octaoxa-16,22,38,44-tetraazatetrabenzo[h,q,z,i ₁]cyclohexatriacontine: a benzoannelated tricyclic cryptand