1,3-Dihydroimidazol-2-one

4-imidazolin-2-one.svg 125px 2-Hydroxyimidazole 5918-93-4 correct CAS 105774 51022 20850 852-506-3 1S/C3H4N2O/c6-3-4-1-2-5-3/h1-2H,(H2,4,5,6) AICIYIDUYNFPRY-UHFFFAOYSA-N C20382 22208 C1=CNC(=O)N1 C658O375NL 3 4 2 1 PubChem 2-Hydroxyimidazole https://pubchem.ncbi.nlm.nih.gov/compound/22208 2026-05-02 pubchem.ncbi.nlm.nih.gov en 05 07 08 Danger 302 314 315 319 335 360D P203 P260 P264 P264+P265 P270 P271 P280 P301+P317 P301+P330+P331 P302+P352 P302+P361+P354 P304+P340 P305+P351+P338 P305+P354+P338 P316 P317 P318 P319 P321 P330 P332+P317 P337+P317 P362+P364 P363 P403+P233 P405 P501 1,3-Dihydroimidazol-2-one is a chemical compound belonging to the group of unsaturated compounds nitrogen heterocycles. It is classified as a lactam and is a derivative of imidazoline and urea. Representation 1,3-Dihydroimidazol-2-one (2) is obtained by reduction of hydantoin (1) with diisobutylaluminum hydride (DIBAH) in tetrahydrofuran.Ralph A. Whitney 1981 10.1016/S0040-4039(01)93277-0 22 2063–2066 Tetrahedron Letters Cycloaddition reactions of 1,3-diacetylimidazolin-2-one 22 frameless|upright=1.2|Reduction of hydantoin to 1,3-dihydroimidazol-2-one The Schwartz reagent can be used as an alternative reducing agent.Srinivasa Reddy Dandepally, Radouane Elgoummadi, Alfred L. Williams 2013 10.1016/j.tetlet.2012.12.015 8 925–928 Tetrahedron Letters Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones and imidazolidine-2,4-diones 54 Another synthetic route is based on 2,2-diethoxyethylamine (1). Reaction with potassium cyanate yields 2,2-diethoxyethylurea (2), which undergoes cyclization under acidic conditions with sulfuric acid to form 1,3-dihydroimidazol-2-one (3).John W. Fischer, Richard A. Hollins, Charlotte K. Lowe-Ma, Robin A. Nissan, Robert D. Chapman 1996 10.1021/jo9613040 26 9340–9343 Journal of Organic Chemistry Synthesis and Characterization of 1,2,3,4-Cyclobutanetetranitramine Derivatives 61 frameless|upright=2.58|text=Synthesis of 1,3-dihydroimidazol-2-one from 2,2-diethoxyethylamine Properties Several tautomeric forms of 1,3-dihydroimidazol-2-one are possible due to keto-enol tautomerism. In addition to 1,3-dihydroimidazol-2-one (1), these include 1H-imidazol-2-ol (2), 4H-imidazol-2-ol (3), and 1,5-dihydroimidazol-2-one (4). The preferred tautomer is 1,3-dihydroimidazol-2-one.Klaus Ebel 1994 10.1055/b-0035-110513 4. 978-3-13-797804-6 Thieme Verlag 1H-Imidazole Struktur, Stabilität, Reaktivität frameless|upright=1.16|keto-enol tautomerism of synthesis at 1,3-dihydroimidazol-2-one Use In organic synthesis, 1,3-dihydroimidazol-2-one serves as a versatile building block for the preparation of substituted vicinal diamines or compounds featuring a cyclic urea structure.Alexis Archambeau 1,3-Dihydroimidazolone 2019 10.1002/047084289X.rn02225 978-0-470-84289-8 1–3 John Wiley & Sons Encyclopedia of Reagents for Organic Synthesis 1,3-Dihydroimidazol-2-one undergoes [2+2]-cycloadditions, for which the diacetylated derivative is typically employed due to solubility considerations. This reaction represents, for example, a key step in a total synthesis of biotin (5). Upon treatment with acetic anhydride, 1,3-dihydroimidazol-2-one (1) is first converted into 1,3-diacetyl-1,3-dihydroimidazol-2-one (2). A subsequent photochemical reaction with 3,4-dihydro-2-methoxy-2H-pyran (3) yields the tricyclic cyclobutane derivative 4, which can be transformed into biotin through several subsequent steps.Ralph Allen Withney 1983 10.1139/v83-206 6 1158–1160 Canadian Journal of Chemistry A total synthesis of (±)-biotin 61 frameless|upright=4.4|Total synthesis of biotin starting from 1,3-dihydroimidazol-2-one References Category:Imidazolines Category:Ureas