Aminolysis of aryl ester using tertiary amine as amino donor via c-o and c-n bond activations
An aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of a broad scope of tertiary amides under neutral and mild conditions. The mechanism may undergo the two key steps of oxidative addition of acyl C-O bond in parent ester and C-N bond cleavage of tertiary amine via an iminium-type intermediate.
Transesterification for synthesis of carboxylates using aldehydes as acyl donors via C-H and C-O bond activations
A new type of transesterification between aryl, heteroaryl, alkyl N-heteroarene-2-carboxylates and various aldehydes by C-H and C-O bond activations has been developed for the synthesis of versatile carboxylates. A possible mechanism containing oxidative addition of acyl-O bond in parent ester and radical cleavage of sp2 C-H bond in aldehyde is proposed.
Bao, Yong-Sheng,Chen, Chao-Yue,Huang, Zhi-Zhen
p. 8344 - 8349,6
(2020/10/15)
1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis
Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.
Cesarini, Sara,Colombo, Nicoletta,Pulici, Maurizio,Felder, Eduard R.,Brill, Wolfgang K.-D.
p. 10223 - 10236
(2007/10/03)
Pentafluorophenyl ester activation for the preparation of N,N'-diaroylhydrazines
Procedures are reported for the preparation of N,N'-diaroylhydrazines using pentafluorophenyl (Pfp) ester activation of aryl carboxylic acids. Mild conditions which avoid intermediate protection of ring substituents, allows the synthesis of both symmetrical and unsymmetrical diaroylhydrazines in high yields. The recent discovery of potent HIV-1 integrase inhibition by N,N'-bis-salicylhydrazine (1) highlights the potential importance of this class of compounds. The stability of pre-activated Pfp ester intermediates and the facility with which N,N'-diaroylhydrazines can be synthesized using this procedure (stirring at room temperature in DMF) may make the method particularly attractive for synthesis of hydrazide libraries.
Zhao, He,Burke Jr., Terrence R.
p. 4219 - 4230
(2007/10/03)
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