Imidazole aus Iminoestern, α‐substituierten Carbonylverbindungen und flüssigem Ammoniak. 5. Mitt. über Imidazolsynthesen mit flüssigem Ammoniak

Wegner, K.; Schunack, Walter

doi:10.1002/ardp.19743071215

Cited by 11 publications

(3 citation statements)

References 15 publications

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“…Several attempts were made for the synthesis of 2-amino-imidazole deri-vatives by reacting α-bromoketones with guani-dines [ 239 , 240 , 241 , 242 , 243 , 244 , 245 , 246 , 247 , 248 , 249 ]. Little and Webber [ 239 ] have observed a clean reaction when α-haloketones were stirred, at room temperature in anhydrous DMF, with excess of N -acetyl-guanidine ( 119 ) to yield the corresponding 4,5-disubstituted N -(1 H -imidazol-2-yl)acetamides 120 , which are then hydrolyzed into 121 .…”

Section: Reactions Of α-Haloketones With Oxygen Nitrogen and Sulfmentioning

confidence: 99%

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

2003

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Section: Reactions Of α-Haloketones With Oxygen Nitrogen and Sulfmentioning

confidence: 99%

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

2003

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“…229 °C, lit . 290–291 °C, lit. , 1 H NMR (400 MHz, CD 3 OD): δ 7.79 (d, J = 7.3 Hz, 2H), 7.40 (t, J = 7.6 Hz, 2H), 7.31 (t, J = 7.4 Hz, 1H), 2.63–2.60 (m, 4H), 1.88–1.85 (m, 4H). 13 C{1H} NMR (150 MHz, CD 3 OD): δ 145.9, 132.1, 131.8, 129.8, 129.2, 125.9, 24.4, 23.5.…”

Section: Methodsmentioning

confidence: 99%

Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration

et al. 2022

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The reactivity of readily available 4,5-fused-1-sulfonyl-1,2,3-triazoles was examined in the Rh(II)-catalyzed transannulation reaction with nitriles. We have come across the interesting observation that 1-sulfonyl cycloalkeno[d][1,2,3]triazoles that possess β-hydrogens resist intramolecular β-hydride migration and could serve as a new source of Rh-iminocarbenoids for intermolecular Rh(II)-catalyzed transannulation reactions. As a result, 1-sulfonyl cyclohexeno-, cyclohepteno-, dihydropyrano-, 5-phenyltetrahydrobenzo-, and 4,5-dihydronaphtho[d]imidazoles were synthesized from various nitriles in good yields. A one-pot methodology has also been executed for the synthesis of NH-imidazoles.

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“…of Five-Membered Rings with Two Heteroatoms1. Imidazoles and Their Fused DerivativesSeveral attempts were made for the synthesis of 2-aminoimidazole derivatives by reacting αbromoketones with guanidines[239][240][241][242][243][244][245][246][247][248][249]. Little and Webber[239] have observed a clean reaction when α-haloketones were stirred, at room temperature in anhydrous DMF, with excess of N-acetylguanidine (119) to yield the corresponding 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides 120, which are then hydrolyzed into 121.…”

mentioning

confidence: 99%