Uber die Synthese von N&lt;SUP&gt;1&lt;/SUP&gt;-substituierten N&lt;SUP&gt;3&lt;/SUP&gt;-Acylguanidinen (Vorlaufige Mitt.). Benzoylverbindungen.

Ito, Genzo

doi:10.1248/cpb.9.245

Cited by 8 publications

(1 citation statement)

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“…Purification was done by flash chromatography on silica gel (cyclohexane/ethyl acetate 8/2 > 1/1) to give the product 5s (0.55 g, 2.03 mmol, 41%) as a white solid: R f (cyclohexane/ethyl acetate 1/1) = 0.18; mp 136.3–136.9 °C (lit. mp 136–137 °C); 1 H NMR (DMSO- d 6 , 500 MHz) δ (ppm) δ 3.76 (s, 3H), 6.90–7.01 (m, 2H), 7.35–7.44 (m, 4H), 7.44–7.49 (m, 1H), 8.05–8.12 (m, 2H), 9.29 (s, 2NH); 13 C{ 1 H} NMR (DMSO- d 6 , 125 MHz) δ (ppm) 176.0, 159.8, 156.2, 138.8, 130.8, 130.6, 128.6, 127.8, 124.5, 114.2, 55.3; IR (cm –1 ) 3465, 3070, 3000, 2970, 1738, 1639, 1596, 1558, 1512, 1442, 1354, 1298, 1250, 1205, 1181, 1106, 1087, 1028, 910, 862, 826, 815, 756, 716, 685; HRMS (ESI) calculated for C 15 H 16 N 3 O 2 [M + H] + : 270.1237, found 270.1234.…”

Section: Methodsmentioning

confidence: 99%

Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

2016

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Recently we introduced iron trichloride as an environmentally benign and cost-efficient reagent for the synthesis of N-benzoylguanidines. This highly attractive synthetic approach grants access to a broad spectrum of N-benzoylguanidines under mild conditions in short reaction times. In this work we present an extended scope of our methodology along with the results obtained from mechanistic studies via in situ IR spectroscopy in combination with LC (liquid chromatography)-MS analyses. On the basis of these new mechanistic insights we were able to optimize the synthetic protocol and to develop an alternative mechanistic proposal. In this context the symbiotic roles of iron trichloride and oxygen in the guanylation process are highlighted.

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Section: Methodsmentioning

confidence: 99%

Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

2016

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2‐Imidazolines. III (1). 1‐Aryl‐ and 1‐acyl‐2‐amino‐(ormethoxy)‐4,5‐diamino‐4,5‐dihydroimidazoles. Synthesis and properties

Citerio

Rivera

Saccarello

et al. 1980

Journal of Heterocyclic Chem

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Diimmonium salt (5) reacts with guanidines (6) and o‐methylisoureas (7) affording 2‐amino‐4,5‐dimorpholinoimidazolines (9). 1‐Aryl‐2‐amino‐4,5‐dimorpholinoimidazolines lose the amino functionality under mild acidic conditions with formation of 2‐amino‐5‐morpholinoimidazole derivatives (10) whereas 1‐acyl derivatives undergo under the same conditions a ring expansion process leading to pyrimidine derivatives (13).

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Synthesis and pharmacological properties of some acyl derivatives of benzylguanidine

et al. 1968

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Uber die Synthese von N<SUP>1</SUP>-substituierten N<SUP>3</SUP>-Acylguanidinen (Vorlaufige Mitt.). Benzoylverbindungen.

Cited by 8 publications

References 0 publications

Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

2‐Imidazolines. III (1). 1‐Aryl‐ and 1‐acyl‐2‐amino‐(ormethoxy)‐4,5‐diamino‐4,5‐dihydroimidazoles. Synthesis and properties

Synthesis and pharmacological properties of some acyl derivatives of benzylguanidine

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