20th Iranian Seminar of Organic Chemistry , 2013-07-03

Title : ( A convenient one-pot method for the synthesis of highly functionalized 1,3-oxazole )

Authors: A. Nikseresht , S. Parak , Mehdi Bakavoli , J. Lari , H. Vahedi ,

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Abstract

1,3-Oxazole derivatives elicit a variety of biological responses [1-2], including anti-cancer and anti-HIV/AIDS activity [3]. We now report a more convenient and versatile method for the synthesis of highly substituted N(9-(2-(5-amino-4-cyano-oxazol-2-yl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-Nethylethanaminium chloridefrom aminomalononitrile tosylate (AMNT, 1)and Rhodamin B such as carboxylic acid derivative. The carboxyl activating reagent, 1,3-dicyclohexylcarbodiimide (DCC), has been used to synthesize 2-substituted 5-amino-4-cyano-1,3-oxazole 2 from AMNT (1) and the appropriate carboxylic acid (Rhodamin B) in the presence of pyridine (Scheme 1). This convenient method afford 1,3-oxazole derivative 2 directly from acid and AMNT (1), and avoids the prior step of preparation of acid chlorides. The DCC coupling method has broader applications. For example, 2hydroxy oxazoles can be prepared directly from hydroxyl acids.

Keywords

, 1, 3-Oxazole derivatives elicit a variety of biological responses [1-2], including anti-cancer and anti-HIV/AIDS activity [3]. We now report a more convenient and versatile method for the synthesis of highly substituted N(9-(2-(5-amino-4-cyano-oxazol-2-yl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylide
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@inproceedings{paperid:1035446,
author = {A. Nikseresht and S. Parak and Bakavoli, Mehdi and J. Lari and H. Vahedi},
title = {A convenient one-pot method for the synthesis of highly functionalized 1,3-oxazole},
booktitle = {20th Iranian Seminar of Organic Chemistry},
year = {2013},
location = {همدان, IRAN},
keywords = {1;3-Oxazole derivatives elicit a variety of biological responses [1-2]; including anti-cancer and anti-HIV/AIDS activity [3]. We now report a more convenient and versatile method for the synthesis of highly substituted N(9-(2-(5-amino-4-cyano-oxazol-2-yl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-Nethylethanaminium chloridefrom aminomalononitrile tosylate (AMNT; 1)and Rhodamin B such as carboxylic acid derivative. The carboxyl activating reagent; 1;3-dicyclohexylcarbodiimide (DCC); has been used to synthesize 2-substituted 5-amino-4-cyano-1;3-oxazole 2 from AMNT (1) and the appropriate carboxylic acid (Rhodamin B) in the presence of pyridine (Scheme 1). This convenient method afford 1;3-oxazole derivative 2 directly from acid and AMNT (1); and avoids the prior step of preparation of acid chlorides. The DCC coupling method has broader applications. For example; 2hydroxy oxazoles can be prepared directly from hydroxyl acids.},
}

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%0 Conference Proceedings
%T A convenient one-pot method for the synthesis of highly functionalized 1,3-oxazole
%A A. Nikseresht
%A S. Parak
%A Bakavoli, Mehdi
%A J. Lari
%A H. Vahedi
%J 20th Iranian Seminar of Organic Chemistry
%D 2013

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