N-Alkyl Carbamoylimidazoles as Isocyanate Equivalents: Exploration of the Reaction Scope for the Synthesis of Ureas, Hydantoins, Carbamates, Thiocarbamates, and Oxazolidinones was written by Bansagi, Jazmin;Wilson-Konderka, Cody;Debrauwer, Vincent;Narayanan, Pournima;Batey, Robert A.. And the article was included in Journal of Organic Chemistry in 2022.COA of Formula: C10H20O This article mentions the following:
The reaction of the HCl or trifluoroacetic acid salts of primary amines R1NH3+Cl– (R1 = Me, Et, propargyl, 2H-1,3-benzodioxol-5-ylmethyl, etc.) with carbonyldiimidazole (CDI) is shown to be a preparatively useful method for forming monosubstituted carbamoylimidazoles I (28 examples) without the formation of sym. urea side products. The utility of these air- and water-stable crystalline carbamoylimidazole reagents was demonstrated by their reactions as blocked or masked isocyanate equivalent Reaction with various classes of nucleophiles provides access to useful functional groups including ureas R1NHC(O)N(R2)R3 (R2 = 2-methylpropyl, (4-chlorophenyl)methyl, 2-phenylethyl; R3 = H, methoxycarbonyl), carbamates R1NHC(O)OR3 (R3 = (2Z)-3,7-dimethylocta-2,6-dien-1-yl, (2S,5S)-5-methyl-2-(propan-2-yl)cyclohexyl, (2-aminophenyl)methyl), thiocarbamates R1NHC(O)SR4 (R4 = n-octyl, phenyl), hydantoins II (R5 = benzyl; R6 = H; R5R6 = -(CH2)4) and oxazolidinones III (R7 = prop-1-en-1-yl, phenyl). A parallel synthesis library of 30 ureas was generated by the reaction of 6x carbamoylimidazole intermediates with 5x amines and triethylamine. The unsym. urea-containing natural products macaurea A and pygmaniline A were also prepared in good yields (95% over four steps and 79% over three steps, resp.) using this approach. The reaction of carbamoylimidazoles I with amino acid Me esters followed by microwave irradiation in aqueous media gives hydantoins II in high yields, further demonstrating the ability of carbamoylimidazoles I as isocyanate surrogates. Three hydantoin-containing natural products including macahydantoin D and meyeniihydantoin A were prepared in nearly quant. yields from proline Me ester and carbamoylimidazoles I. The reaction of carbamoylimidazoles I with alcs. R3OH and thiols R4SH under basic conditions affords carbamates and thiocarbamates, resp., in good yields. Lastly, a method for the preparation of chiral oxazolidinone heterocycles III from chiral epoxy alcs. IV is demonstrated using a double displacement approach. The reactions occur with high regio- and stereoselectivity (dr ≥ 15:1 by 1H NMR) via a domino attack of the corresponding alkoxides with carbamoylimidazoles followed by an intramol. attack of the in situ generated urea anion at the proximal position of the epoxide group. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5COA of Formula: C10H20O).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.COA of Formula: C10H20O
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