Synthesis and conformational analysis of N-aryl-N-(6-azulenyl)acetamides

Ito, Ai; Ishii, Ayako; Amaki, Takamasa; Fukuda, Kazuo; Yamasaki, Ryu; Okamoto, Iwao

doi:10.1016/j.tetlet.2019.06.029

Cited by 4 publications

(3 citation statements)

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“…We previously reported the synthesis of N -arylacetamide derivatives by means of the coupling reaction of aryl halide and acetamides in the presence of CuI as a catalyst. , On the basis of our previous report, N -(2-thienyl)acetamides 2a – 2f and N -(3-thienyl)acetamides 3a – 3f were synthesized by Cu-catalyzed coupling reaction of 2- or 3-bromothiophene and corresponding acetamide derivatives 1a – 1f at 110 °C. Compounds 1a – 1f were either commercially available or prepared from amine derivatives using acetic anhydride. , The results are summarized in Scheme .…”

Section: Results and Discussionmentioning

confidence: 99%

“…17,18 We also found that the conformational preferences of N,Ndiaryl amides were dependent on the size of the aromatic ring on the amide nitrogen. 19,20 That is, the three-dimensional relationships around the aryl groups can influence the conformational preferences of the amides, especially when the aromatic ring is small. Recently, we reported a conformational analysis of N-aryl-N- (3-thienyl)acetamides.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Conformational Analysis of N-Aromatic Acetamides Bearing Thiophene: Effect of Intramolecular Chalcogen–Chalcogen Interaction on Amide Conformational Stability

et al. 2023

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The conformations of aromatic amides bearing an N-(2-thienyl) or N-(3-thienyl) group were investigated in solution and in the crystal state. NMR spectral data indicate that the conformational preferences of these amides in solution are dependent not only on the relative π-electron densities of the N-aromatic moieties, but also on the three-dimensional relationship between carbonyl oxygen and the N-aromatic moieties. A comparison of the conformational preferences of N-(2-thienyl)amides and N-(3-thienyl)amides revealed that the Z-conformers of N-(2-thienyl)acetamides are stabilized by 1,5-type intramolecular S···OC interactions between amide carbonyl and thiophene sulfur. The crystal structures of these compounds were similar to the solution structures. The stabilization energy due to 1,5-type intramolecular S···OC interaction in N-aryl-N-(2-thienyl)acetamides and N-methyl-N-(2-thienyl)acetamide was estimated to be ca. 0.74 and 0.93 kcal/mol, respectively.

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Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Conformational Analysis of N-Aromatic Acetamides Bearing Thiophene: Effect of Intramolecular Chalcogen–Chalcogen Interaction on Amide Conformational Stability

et al. 2023

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“…Typically, diethyl 2-amino-6-bromoaza-1,3-dicarboxylate (4) and 2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) azulene-1,3-dicarboxylate (5) were synthesized according to the literature with minor modification. 15 Then, 5 reacted with 5,10,15,20-tetra (4 0 -bromophenyl) porphyrin (denoted as BrTPP, synthesized according to the reported literture 16 ) to produce TAPP. To study the chemical state of Fe in FeTAPP, Fe X-ray absorption spectroscopy was tested.…”

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confidence: 99%