- Facile esterification of alcohols with 2-Acyl-4,5-dichloropyridazin-3(2 H)-ones under Friedel-Crafts conditions
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This paper describes the esterification of aromatic and aliphatic alcohols by using 2-acyl-4,5-dichloropyridazin-3(2H)-ones as an acyl source under Friedel-Crafts conditions. Twelve alcohols were reacted with four 2-acyl-4,5-dichloropyridazin-3(2H)-ones in the presence of AlCl3 in tetrahydrofuran at room temperature to give the corresponding esters in moderate to excellent yields. Thus, 2-acylpyridazin-3(2H)-ones serve as good and atom-economic acyl sources for the esterification of aromatic alcohols under Friedel-Crafts conditions, representing a rapid, practical, and efficient method of esterification. Georg Thieme Verlag Stuttgart. New York.
- Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Yoon, Hyo Jae,Lee, Sang-Gyeong,Yoon, Yong-Jin
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p. 1909 - 1915
(2014/08/18)
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- Rapid and Ecofriendly Esterification of Alcohols with 2-Acylpyridazinones
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Atom-economical esterification is of great importance in green chemistry. In this work, we demonstrated the catalyst and additive free esterification of alcohols by their reaction with 2-acyl-4,5-dichloropyridazin-3(2H)- ones without solvent at 100 oC. Aliphatic and aromatic alcohols were converted into the corresponding esters in good to excellent yields. It is noteworthy that the reaction is solvent-free, atom-economic, easy-workup, and rapid and that the process is inexpensive.
- Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Kim, Jeum-Jong,Yoon, Yong-Jin
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p. 3410 - 3414
(2014/01/06)
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- EFFECTS OF HETEROATOM SUBSTITUENTS ON THE PROPERTIES OF 1,2-DIOXETANES
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Nitrogen and sulfur-substituted dioxetanes exhibit dramatically lower activation energies for decomposition compared to the corresponding oxygen-bearing dioxetane.A mechanism involving intramolecular electron-transfer processes is proposed for the cleavage of these unstable dioxetanes.
- Handley, Richard S.,Stern, Alan J.,Schaap, A. Paul
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p. 3183 - 3186
(2007/10/02)
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- ACTIVATION OF CARBOXYL GROUPS BY DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE. FACILE PREPARATION OF VERSATILE REAGENTS, 3-ACYL-2-OXAZOLONES
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Synthetic utility of the 2-oxazolone moiety as an excellent new leaving group is described.Based on such a function of the heterocycles, diphenyl 2-oxo-3-oxazolinylphosphonate has been newly introduced as a carboxyl-activating reagent which permits a facile direct preparation of 3-acyl-2-oxazolones and amides including peptides from a wide variety of carboxylic acids.The 3-acyl-2-oxazolides also serve as versatile reactive agents for highly chemoselective acyl-transfer to the nucleophilic species such as amines, alcohols and thiols, providing convenient and high-yield routes to amides, esters and thiol esters under mild conditions.They are also useful intermediates for ketones and alcohols.
- Kunieda, Takehisa,Higuchi, Tsunehiko,Abe, Yoshihiro,Hirobe, Masaaki
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p. 3253 - 3260
(2007/10/02)
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