Complete assignment of NMR data of 22 phenyl‐1H‐pyrazoles' derivatives

Complete assignment of ¹H and ¹³C NMR chemical shifts and J(¹H/¹H and ¹H/¹⁹F) coupling constants for 22 1‐phenyl‐1H‐pyrazoles' derivates were performed using the concerted application of ¹H 1D and ¹H, ¹³C 2D gs‐HSQC and gs‐HMBC experiments. All 1‐phenyl‐1H‐pyrazoles' derivatives were synthesized as described by Finar and co‐workers. The formylated 1‐phenyl‐1H‐pyrazoles' derivatives were performed under Duff's conditions. Copyright © 2011 John Wiley & Sons, Ltd.     

One‐step synthesis of 6‐acetamido‐3‐(N‐(2‐(dimethylamino) ethyl) sulfamoyl) naphthalene‐1‐yl 7‐acetamido‐4‐hydroxynaphthalene‐2‐sulfonate and its characterization with 1D and 2D NMR techniques

A one‐step method was reported for the synthesis of 6‐acetamido‐3‐(N‐(2‐(dimethylamino) ethyl) sulfamoyl) naphthalene‐1‐yl 7‐acetamido‐4‐hydroxynaphthalene‐2‐sulfonate by treating 7‐acetamido‐4‐hydroxy‐2‐naphthalenesulfonyl chloride with equal moles of N, N‐dimethylethylenediamine in acetonitrile in the presence of K₂CO₃. The chemical structure of the obtained compounds was characterized by MS, FTIR, ¹H NMR, ¹³C NMR, gCOSY, TOCSY, gHSQC, and gHMBC. The chemical shift differences of ¹H and ¹³C being δ 0.04 and 0.2, respectively, were unambiguously differentiated. Copyright © 2013 John Wiley & Sons, Ltd.     

NMR studies on 1,2‐dihydro‐2‐(4‐aminophenyl)‐4‐[4‐(4‐aminophenoxy)‐4‐phenyl]‐(2H)phthalazin‐1‐one

An unsymmetrical heterocyclic diamine, 1,2‐dihydro‐2‐(4‐aminophenyl)‐4‐[4‐(4‐aminophenoxy)‐4‐phenyl]‐(2H)phthalazin‐1‐one, was synthesized. Its ¹H and ¹³C NMR spectra were completely assigned by utilizing the two‐dimensional heteronuclear ¹³C–¹H multiple‐bond coherence (HMBC) spectroscopy, and heteronuclear ¹³C–¹H one‐bond correlation spectroscopy, homonuclear shift correlation spectroscopy (H,H‐COSY) and rotating frame Overhauser enhancement spectroscopy (ROESY). The structure of the compound was shown to be the phthalazinone rather than the phthalazine ether from cross peaks and chemical shifts of the protons. Copyright © 2002 John Wiley & Sons, Ltd.     

Synthesis and NMR characteristics of N‐acetyl‐4‐nitro,N‐acetyl‐5‐nitro,N‐acetyl‐6‐nitro and N‐acetyl‐7‐nitrotryptophan methyl esters

N‐acetyl‐4‐nitrotryptophan methyl ester (2), N‐acetyl‐5‐nitrotryptophan methyl ester (3), N‐acetyl‐6‐nitrotryptophan methyl ester (4) and N‐acetyl‐7‐nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF₃‐methanol. Assignments of the ¹H and ¹³C NMR chemical shifts were made using a combination of ¹H–¹H COSY, ¹H–¹³C HETCOR and ¹H–¹³C selective INEPT experiments. Copyright © 2008 Crown in the right of Canada. Published by John Wiley & Sons, Ltd     

Isolation and spectral study of 4‐methyl‐6,8‐dihydroxy‐7H‐benz[de]anthracen‐7‐one

4‐Methyl‐6,8‐dihydroxy‐7H‐benz[de]anthracen‐7‐one was isolated from the sap of Aloe by column chromatography. Its ¹H and ¹³C NMR spectra were completely assigned by utilizing two‐dimensional ¹H‐detected heteronuclear one‐bond (HMQC) and multiple‐bond (HMBC) chemical shift correlation experiments together with ¹H–¹H COSY and DEPT techniques. These techniques were also valuable in assigning the protons and carbons of those benzanthrone compounds which were previously incompletely reported because of the overlap of proton signals. The molecular structure was elucidated by 2D NMR analysis. The spectral properties (MS, IR and UV) are also presented. Copyright © 2003 John Wiley & Sons, Ltd.     

1H and 13C NMR spectral characterization of some antimalarial in vitro 2,4‐diamino‐10‐methylpyrimido[4,5‐b]‐5‐quinolone derivatives

We report the ¹H NMR and ¹³C NMR chemical shifts and J(H,H), J(H,F) and J(C,F) coupling constants of 13 2,4‐diamino‐10‐methylpyrimido[4,5‐b]‐5‐quinolone derivatives, some of them with moderate activity against Plasmodium falciparum in vitro. They were characterized and assigned on the basis of ¹H, ¹³C and ¹³C–¹H (short‐ and long‐range) correlated spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

NMR analysis of 6‐(2′,3′‐dihydro‐1′H‐inden‐1′‐yl)‐1H‐indene

¹H, ¹³C and two‐dimensional NMR analyses were applied to determine the NMR parameters of 6‐(2′,3′‐dihydro‐1′H‐inden‐1′‐yl)‐1H‐indene. The measurements were accomplished with 0.5 mg of the substance, this quantity being sufficient to determine the chemical shifts of all the H and C atoms, and also the appropriate coupling constants and to give the complete NMR resonance assignments of the molecule. The predicted patterns of the four different H atoms of the methylene groups of the indane structural element coincided completely with the complex patterns in the NMR spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

1H and 13C NMR spectral assignments of pyridinium salts linked to a N‐9 or N‐3 adenine moiety

¹H and ¹³ C NMR spectral data of 13 new compounds containing a 4‐(dimethylamino)‐ or 4‐(pyrrolidin‐1‐yl)pyridinium moiety linked to the N‐9 or N‐3 nitrogen atom of an adenine moiety were assigned. 1D and 2D NMR experiments (DEPT, HSQC and HMBC) allowed the unequivocal identification of N‐9 and N‐3 isomers. Copyright © 2012 John Wiley & Sons, Ltd.     

Conformational analysis. Part 40: a theoretical and NMR investigation of the conformations of cis‐ and trans‐cyclopentane‐1,3‐diol

The conformations of cis‐ ( 1 ) and trans‐cyclopentane‐1,3‐diol ( 2 ) have been studied by ab initio (Gaussian 98) and molecular mechanics (PCMODEL) calculations and by NMR spectroscopy. The calculations gave two low‐energy conformations for ( 1 ), 1A and 1B , both with axial hydroxyl groups. Two conformations with equatorial hydroxyl groups ( 1C and 1D ) were found but with much higher energy (ca 4.0 kcal mol^?1). Five low‐energy conformers were found for 2 . Four were envelope conformations and one a half‐chair. The complete analysis of the 400 MHz ¹H NMR spectra of 1 in a variety of solvents and 2 in chloroform was performed by extensive decoupling experiments, iterative computer analysis and spectral simulation. This gave all the H,H couplings in the molecule, including in 1 a long‐range ⁴J(H,H) coupling between H‐2cis and H‐4,5cis. The ³J(H,H) couplings were used to determine the conformer populations in these molecules. This was initially achieved using the Haasnoot, de Leeuw and Altona equation. to obtain the conformer couplings. It was found that this equation was not accurate for the C·CH₂·CH₂·C fragment in these molecules and the following equation was derived for this fragment from five‐ and six‐ membered cyclic compounds in fixed conformations: (1) The conformer populations were obtained by calculating the conformer couplings which were then compared with the observed couplings. Compound 1 in benzene solution is an approximately equal mixture of conformers 1A and 1B with small (<4%) amounts of 1C and 1D . In the polar solvents acetone and acetonitrile the populations of 1A and 1B are again equal, with 20% of 1C and <2% of 1D . In 2 the major conformers are 2B and 2D with small amounts of 2C , 2E and 2A . These novel findings are considered with previous data on cyclopentanol and cis‐ and trans‐cyclopentane‐1,2‐diol and it is shown that the axial hydroxyl substituent at the fold of the envelope appears to be a major factor in determining the conformational energies of these compounds. Copyright © 2003 John Wiley & Sons, Ltd.     

Structural determination of aspericins A?C,new furan and pyran derivates from the marine‐derived fungus Rhizopus sp. 2‐PDA‐61, by 1D and 2D NMR spectroscopy

Three new furan and pyran derivatives named aspericins A? C (1–3), as well as a known asperic acid (4), have been isolated from the marine‐derived fungus Rhizopus sp. 2‐PDA‐61. The complete ¹H and ¹³C NMR assignments for the new compounds were carried out using ¹H, ¹³C, DEPT, COSY, HMQC, HMBC, and NOESY NMR experiments. Compounds 1–3 were evaluated for their cytotoxic activities on P388, A549, HL‐60, and BEL‐7420 cell lines by the MTT and SRB methods. Copyright © 2009 John Wiley & Sons, Ltd.     

NMR analysis of mono‐ and difructosyllactosucrose synthesized by 1F‐fructosyltransferase purified from roots of asparagus (Asparagus officinalis L.)

Two novel oligosaccharides, mono‐ and difructosyllactosucrose {[O‐β‐D ‐fructofuranosyl‐(2 → 1)]_n‐β‐D ‐fructofuranosyl‐O‐[β‐D ‐galactopyranosyl‐(1 → 4)]‐α‐D ‐glucopyranoside, n = 1 and 2} were synthesized using 1^F‐fructosyltransferase purified form roots of asparagus (Asparagus officinalis L.). Their ¹H and ¹³C NMR spectra were assigned using several NMR techniques. The spectral analysis was started from two anomeric methines of aldose units, galactose and glucose, since they showed separate characteristic signals in their ¹H and ¹³C NMR spectra. After assignments of all the ¹H and ¹³C signals of two units of aldose, they were discriminated as galactose and glucose using proton–proton coupling constants. The HMBC spectrum revealed the galactose residue attached to C‐4 of glucose, fructose residue attached to the C‐1 of glucose, and further fructosyl fructose linkage extended from the glucosyl fructose residues. Copyright © 2002 John Wiley & Sons, Ltd.     

Synthesis and 1H and 13C NMR structural analysis of cis‐ and trans‐2‐imino‐1,3‐ and ‐3,1‐perhydrobenzoxazines and their 3‐ and 1‐N‐methyl derivatives

cis‐ and trans‐2‐imino‐1,3‐ and ‐3,1‐perhydrobenzoxazines and the N‐methyl derivatives of the latter were synthesized from the corresponding cyclic 1,3‐amino alcohol with cyanogen bromide. The configurations of the studied compounds were confirmed by ¹H and ¹³C NMR spectra. All trans‐fused compounds exist in biased chair–chair conformations as expected, whereas the cis‐fused 1,3‐benzoxazines attain exclusively the O‐in conformations. The cis‐fused 3,1‐benzoxazines, especially the 1‐methyl‐substituted derivatives, tend to favor the N‐out form, obviously owing to the favorable axial orientation of this N‐methyl. Copyright © 2003 John Wiley & Sons, Ltd.     

1H and 13C NMR analysis of 2‐acetamido‐3‐mercapto‐3‐methyl‐N‐aryl‐butanamides and 2‐acetamido‐3‐methyl‐3‐nitrososulfanyl‐N‐aryl‐butanamide derivatives

The complete assignment of the ¹H and ¹³C NMR spectra of various 2‐acetamido‐3‐mercapto‐3‐methyl‐N‐aryl‐butanamides and 2‐acetamide‐3‐methyl‐3‐nitrososulfanyl‐N‐aryl‐butanamides with p‐methoxy, o‐chloro and m‐chloro substituents is reported. Copyright © 2013 John Wiley & Sons, Ltd.     

Complete NMR assignment of 3, 4‐seco‐lup‐20(29)‐en‐3‐oic acid from Decatropis bicolor

Complete ¹H and ¹³C NMR chemical shift assignments for 3,4‐seco‐lup‐20(29)‐en‐3‐oic acid ( 1 ) have been established by means of two‐dimensional COSY, HSQC, HMBC and NOESY spectroscopic experiments as well as by analysis of MS data. Compound 1 was isolated from Decatropis bicolor (Zucc.) Radlk. (Rutaceae) in addition to six coumarins and one alkaloid of known structure. Copyright © 2012 John Wiley & Sons, Ltd.     

1H and 13C NMR data of methyl tetra‐O‐benzoyl‐D‐pyranosides in acetone‐d6

Complete assignments of ¹H‐ and ¹³C‐NMR resonances of five methyl tetra‐O‐benzoyl‐D‐pyranosides based on ¹H, ¹³C, 2D DQF–COSY, HMQC, HMBC and HSQC–TOCSY experiments have been performed. Copyright © 2009 John Wiley & Sons, Ltd.     

Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (1H, 13C, 15N) data

Various [5,6]pyrano[2,3‐c]pyrazol‐4(1H)‐thiones were synthesized in high yields by treatment of the corresponding [5,6]pyrano[2,3‐c]pyrazol‐4(1H)‐ones with Lawesson's reagent. Detailed NMR spectroscopic studies were undertaken of the title compounds. Complete and unambiguous assignment of chemical shifts (¹H, ¹³C, ¹⁵N) and coupling constants (¹H,¹H; ¹³C,¹H) was achieved by the combined application of various one‐ and two‐dimensional (1D and 2D) NMR spectroscopic techniques. Unequivocal mapping of most ¹³C,¹H spin coupling constants is accomplished by 2D (δ, J) long‐range INEPT spectra with selective excitation. Copyright © 2010 John Wiley & Sons, Ltd.     

Complete assignment of 1H and 13C NMR spectra of α‐phenylsulfinyl‐N‐methoxy‐ N‐methylpropionamide and some p‐substituted derivatives

The complete assignment of the ¹H and ¹³C NMR spectra of the diastereomeric pairs of some α‐arylsulfinyl‐substituted N‐methoxy‐N‐methylpropionamides with the substituents methoxy, methyl, chloro, nitro is reported. Copyright © 2008 John Wiley & Sons, Ltd.     

Complete assignment of the 1H and 13C NMR spectra of four 2‐substituted 4a,8a‐cis‐endo‐5,8‐methano‐4a,5,8,8a‐tetrahydronaphthalene‐1,4‐diones

The complete assignment of the ¹H and ¹³C NMR spectra of the title enediones, bearing as substituents N‐aziridinyl (a novel compound), methoxy, chloro and methylsulfanyl, is reported. Copyright © 2002 John Wiley & Sons, Ltd.     

Assignment of 1H and 13C NMR data for diethyl 2‐ and 8‐quinolylmethylphosphonates and their palladium(II) dihalide complexes

¹H and ¹³C NMR spectral data for diethyl 2‐ and 8‐quinolylmethylphosphonates (L) and their palladium(II) dihalide complexes, trans‐[PdL₂X₂] (L = 2‐dqmp, 8‐dqmp; X = Cl, Br), are presented. The NMR analysis was performed on the basis of one‐ and two‐dimensional homo‐ and heteronuclear experiments including ¹H, ¹³C, APT, ¹H–¹H COSY, ¹H–¹³C COSY, HMQC and HMBC techniques. Copyright © 2003 John Wiley & Sons, Ltd.     

Structure elucidation of [1,3]oxazolo[4,5‐e][2,1]benzisoxazole and naphtho[1,2‐d][1,3]‐ and phenanthro[9,10‐d]oxazoles using gradient selected gHMBC,gHMQC and gHMQC‐TOCSY NMR techniques

Structure elucidation of compounds in the benzisoxazole series ( 1 – 6 ) and naphtho[1,2‐d][1,3]‐ ( 7 – 10 ) and phenanthro[9,10‐d][1,3]oxazole ( 11 – 14 ) series was accomplished using extensive 2D NMR spectroscopic studies including ¹H–¹H COSY, long‐ range ¹H–¹H COSY, ¹H–¹³C COSY, gHMQC, gHMBC and gHMQC‐TOCSY experiments. The distinction between oxazole and isoxazole rings was made on the basis of the magnitude of heteronuclear one‐bond ¹J_{C2, H2} (or ¹J_{C3, H3}) coupling constants. Complete analysis of the ¹H NMR spectra of 11 – 14 was achieved by iterative calculations. Gradient selected gHMQC‐TOCSY spectra of phenanthro[9,10‐d][1,3]oxazoles 11 – 14 were obtained at different mixing times (12, 24, 36, 48 and 80 ms) to identify the spin system where the protons of phenanthrene ring at H‐5, H‐6 and at H‐9 and H‐7 and H‐8 were highly overlapping. Copyright © 2003 John Wiley & Sons, Ltd.