Synthesis of β-Dicarbonyl Compounds Using 1-Acylbenzotriazoles as Regioselective C-Acylating Reagents

Abstract

1-Acylbenzotriazoles 1 are efficient C-acylation reagents for the regioselective conversion of ketone enolates 2 into beta-diketones 3.

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…C-Acylation of N-acylbenzotriazoles with furan, thiophene, pyrrole, and indole under Friedel-Crafts conditions gave products in high yields [154]. b-Diketones have been prepared from monoketones and N-acylbenzotriazoles in the presence of base [155]. a-Substituted b-ketonitriles have been synthesized from N-acylbenzotriazoles with primary and secondary alkyl nitriles [156].…”

A convenient access to 1-substituted-2-azinyl-1-ethanones via acylation of alkylated azines with N-acylbenzotriazoles

“…The starting N-acylbenzotriazoles 8a−f with alkyl, alkenyl or aryl substituents (R = isobutyl, nbutyl, cinnamyl, phenyl, 4-chlorophenyl or 4-nitrophenyl) were prepared by stirring acid chlorides in CH 2 Cl 2 with benzotriazole in the presence of Et 3 N at room temperature 28 …”

Molecular and Solid State Structure of the Doubly-Substituted B-Diketone 3,3'-Bis(ferrocenylmethyl)pentane-2,4-Dione#

“…β-Diketones are an important class of organic compounds frequently encountered in synthetic chemistry, 1,2 where in addition to their established role in the synthesis of various heterocyclic derivatives which have been widely studied and reviewed, [3][4][5][6] they have been used as ligands for the coordination of transition metals. 7,8 On the other hand, β-diketones are attractive building blocks for the construction of polydentate Schiff bases, and both the parent derivative 2,4-pentanedione (CH 3 COCH 2 COCH 3 ), [9][10][11][12] and its organometallic counterpart ferrocenoylacetone (FcCOCH 2 COCH 3 , 13 Fc = (h 5 -C 5 H 5 )Fe(h 5 -C 5 H 4 )) have been widely employed to prepare tridentate Schiff base complexes, also called half-units, upon mono-condensation with primary diamines.…”