70990-68-0Relevant articles and documents
Synthesis of unsymmetrical urea derivativesviaone-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes
He, Xinwei,Yang, Cheng,Wu, Yinsong,Xie, Mengqing,Li, Ruxue,Duan, Jiahui,Shang, Yongjia
supporting information, p. 4178 - 4182 (2020/06/21)
A novel and efficient multicomponent reaction of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes has been developed, and it leads to unsymmetrical urea derivatives with good yields in a single operation. This transformation involves the cascade formation of C-X (X = Cl, Br, I), C-N and C-O bonds through halogenation, nucleophilic addition, ring-opening, and enol-ketone tautomerization processes. This protocol is step- and atom-economical; 1,2-dihaloethane was used as an easily available halogenated reagent, and it is amenable to different functional groups.
REARRANGEMENT OF 2-ACYL-2-CHLORO-1,3-CYCLOHEXANEDIONES INTO 2-ACYLRESORCINOLS AND 2-ACYL-4-CHLORO-1,3-CYCLOHEXANEDIONES
De Buyck, L.,Seynaeve, D.,De Kimpe, N.,Verhe, R.,Schamp, N.
, p. 363 - 370 (2007/10/02)
2-Acetylresorcinol was prepared in 80-88percent yield from 2-acetyl-1,3-cyclohexanedione by 2-chlorination (excess of NCS in boiling carbon tetrachloride or one equivalent of molecular chlorine in the cold solvent) followed by aromatization in a heated dry solution of hydrogen chloride in dimethylformamide.The scope of the method was extended to the preparation of 2-propionyl- and 2-isobutyrylresorcinol (resp. 79percent and 66percent yield).Application of the method on 2-acryl-5,5-dimethyl-1,3-cyclohexanediones (acyl=acetyl, propionyl, n-butyryl, i-butyryl) affrded the corresponding 2-acyl-4-chlorodimedone derivatives in 40-77percent yields.