87697-27-6Relevant academic research and scientific papers
A new and efficient route for the synthesis of naturally occurring catecholamines
Bernini, Roberta,Crisante, Fernanda,Barontini, Maurizio,Fabrizi, Giancarlo
experimental part, p. 3838 - 3842 (2010/03/30)
Catecholamines, sympathomimetic drugs and adrenergic receptor antagonists, have been prepared by a regioselective oxidation of the corresponding 4-hydroxyphenethylamine derivatives by 2-iodoxybenzoic acid (IBX) in homogeneous as well as in heterogeneous conditions and followed by cleavage of the amino protective group. By using polymer-supported IBX, after the first oxidation, the oxidant can be recovered, regenerated, and efficiently reused for several additional times. An efficient, easy and green procedure for the synthesis of N-(methoxycarbonyl)dopamine, key component of many pharmaceuticals, has also been reported. Georg Thieme Verlag Stuttgart.
A Convenient Synthesis of (Acyloxy)alkyl α-Ethers of Phenols
Bodor, Nicholas,Sloan, Kenneth B.,Kaminski, James J.,Shih, Chung,Pogany, Stefano
, p. 5280 - 5284 (2007/10/02)
(Acyloxy)alkyl α-ethers (1) of phenols, thiophenol, and catechols have been prepared in good yield by their alkylation with (acyloxy)alkyl α-chlorides or iodides in acetone in the presence of K2CO3.In addition, one example of an (acylthio)alkyl α-ether was prepared.Either partial or complete acylation rather than alkylation on oxygen took place if the α-iodide was not used except for reactions of 3-chloro-1(3H)-isobenzofuranone with phenol or catechol or the reaction of (benzoylthio)methyl chloride with β-estradiol.It is suggested that more alkylation takes place with iodide as a leaving group because of the tighter transition state that develops with the better nucleofuge.The alkylation reaction sequence has two advantages for the synthesis of 1: (1) the mildness of the reaction conditions and (2) the wide variety of acyl and alkyl groups that can be incorporated into the product through the (acyloxy)alkyl α-halides.
Novel sypathomimetic amine prodrugs
-
, (2008/06/13)
Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): STR1 wherein X is O, S or NR5 ; n is 1 or 2; R1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy n
