The First Synthesis of N-Alkyl-N-Arylthiocarbamoylacetates and Acetic Acids

Spears, Glen W.; Tsuji, Kiyoshi; Tojo, Takashi; Nishimura, Hiroaki; Ogino, Takashi

doi:10.1080/00397910008087354

Cited by 9 publications

(3 citation statements)

References 7 publications

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“…3,5-Difluoro-N-methylbenzenamine (3e) 18 . Oil, 1 H NMR (500 MHz, CDCl 3 ) d 6.14-6.10 (m, 1H, ArH), 6.08-6.05 (m, 2H, ArH), 3.94 (br s, 1H, NH), 2.79 (s, 3H, CH 3 ); 13 N-Methyl-4-(trifluoromethoxy)benzenamine (3g) 20 . Oil, 1 H NMR (500 MHz, CDCl 3 ) d 7.03 (d, J = 8.3 Hz, 2H, ArH), 6.54 (d, J = 8.9 Hz, 2H, ArH), 3.76 (br s, 1H, NH), 2.81(s, 3H, CH 3 ); 13 Scheme 3 Reaction of N-methylamine 3a with 2.…”

Section: Experimental Section General Experimental Detailsmentioning

confidence: 99%

General and efficient method for direct N-monomethylation of aromatic primary amines with methanol

Xie

Shan

et al. 2012

RSC Adv.

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Section: Experimental Section General Experimental Detailsmentioning

confidence: 99%

General and efficient method for direct N-monomethylation of aromatic primary amines with methanol

Xie

Shan

et al. 2012

RSC Adv.

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“…Different possible routes are amidation cross-coupling reactions, [28][29][30][31][32] Beckmann rearrangement of ketoximes, [33][34][35][36] formation of azido intermediates convertible into amide derivatives, [37] or formation of isocyanate intermediates through Curtius rearrangement of acyl azides. Different possible routes are amidation cross-coupling reactions, [28][29][30][31][32] Beckmann rearrangement of ketoximes, [33][34][35][36] formation of azido intermediates convertible into amide derivatives, [37] or formation of isocyanate intermediates through Curtius rearrangement of acyl azides.…”

Section: Introductionmentioning

confidence: 99%

2,5‐Diamide‐Substituted Five‐Membered Heterocycles: Challenging Molecular Synthons

Fabbro¹,

Armani²,

Carloni³

et al. 2014

Eur J Org Chem

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We describe synthetic routes for preparing previously unknown 2,5‐diamide‐substituted five‐membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius‐like rearrangement reactions. Conformation analysis of the 2,5‐diamidothiophene derivatives identified a “closed” conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.

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“…The filtrate was evaporated in vacuo to give a crude product, which was purified by chromatography [silica gel, hexane → ethyl acetate/ hexane (1:3)] to give 2g (86 mg, 28%). mp 55.5−56.0 °C (lit., 51 49− 53 °C), colorless prisms. IR (KBr) (cm −1 ): 2922, 1674, 1508, 1396, 1315.…”

Section: N-methyl-n-(2-thienyl)acetamide (2g)mentioning

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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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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The First Synthesis of N-Alkyl-N-Arylthiocarbamoylacetates and Acetic Acids

Cited by 9 publications

References 7 publications

General and efficient method for direct N-monomethylation of aromatic primary amines with methanol

General and efficient method for direct N-monomethylation of aromatic primary amines with methanol

2,5‐Diamide‐Substituted Five‐Membered Heterocycles: Challenging Molecular Synthons

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

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