A Simple Access to the Synthesis of 5,6- Dihydro-4H-1,3-oxazines Under Solvent Free Condition and Microwave Irradiation
نویسندگان
چکیده
2-Arylsubstituted 5,6-dihydro-4H-1,3-oxazines were conveniently synthesized by the condensation of 3-aminopropanol and desired carboxylic acids under solvent free and microwave conditions in short reaction times with moderate to good yields. A comparison of this method with the classical protocols using acid halides and nitrile substrates was also made. INTRODUCTION The synthetic utility of dihydro-1,3-oxazines as useful intermediate for the synthesis of ketones [1], unusual aldehydes, such as trans βinoylidene acetaldehyde [2-5], carboxylic acids, stereoselective synthesis of trans-olefins, complex heterocyclic systems and biologically active compounds has been well documented [6-8]. Recently 1,3-oxazine ring system was employed in the design of a molecular switch based on the photoinduced opening and thermal closing of the oxazine ring [9]. Several synthetic approaches to 1,3oxazine derivatives have been reported in the literatures. Some examples of these methods are: using azido-1-propanol [10], Ritter reaction consists of reacting a diol with a nitrile under strongly acidic conditions [11], synthesis utilizing nitriles and aminoalcohols in the presence of a mild Lewis acid (Cu(OAc)2, ZnCl2) as a catalyst [12], the [4+2] cycloaddition of an N-acylimine and an alkene [13], using N-acyl-4-acyloxy-βlactams under basic conditions [14], intramolecular hydroamination of trichloroacetimidate in the presence of Au(I) complex [15], cycloaddition reactions using 2-azadienes with electron-
منابع مشابه
H3PW12O40: An Efficient and Recyclable Heterogeneous Catalyst for the Selective Synthesis of 2-Aryl-5,6-dihydro-4H-1,3-oxazines and 2-Aryl-1,4,5,6-tetrahydropyrimidines
An environmentally friendly and highly efficient procedure has been developed for the selective synthesis of 2-aryl-5,6-dihydro-4H-1,3-oxazines and 2-aryl-1,4,5,6-tetrahydropyrimidines by cyclocondensation of arylnitriles with 3-amino-1-propanol and 1,3-diaminopropane in the presence of catalytic amounts of H3PW12O40 under thermal conditions and MW irradiation. Under the same reaction condition...
متن کاملGreen procedure for synthesis of 3, 4 dihydropyrimidinones using 12-molybdophosphoric acid, as a catalyst and solvent free condition under microwave irradiation
Simple and improved conditions have been found to carry out the Biginelli reaction for the synthesis of 3, 4-dihydropyrimidin-2(1H) - one derivatives. This synthesis was performed in the presence of 12-molybdophosphoric acid (H3PMo12O40) as catalyst. These reactions were performed under solvent free conditions with microwave irradiation as the energy source. Compared with the classical Biginell...
متن کاملOne-pot synthesis of Benzimidazole derivatives under microwave Irradiation and solvent-free condition
A simple, fast, efficient and environmentally friendly method for synthesis of benzimidazole and its 2-alkyl, aryl and heteroaryl substituted derivatives was developed using zeolite HY. Two component cyclolcondensation of 1,2-phenylenediamine (o-phenylenediamine) and commercially available carboxylic acids catalyzed by zeolite HY without any solvent, under microwave irradiation led to formation...
متن کاملA Facile One-Pot Solvent-Free Synthesis of 1,2-Dihydro-1-arylnaphtho [1,2-e] [1,3] oxazine-3-ones Catalyzed by Nano-Fe2O3
One of the most important goals in medicinal chemistry is the development of new techniques and new heterocyclic compounds with pharmaceutical activity. The present study aimed to use a method for the synthesis of some 1,2-Dihydro-1-arylnaphtho [1,2-e] [1,3] oxazine-3-ones. The question this study tried to answer was this reaction can be performed in present of nano-Fe2O3 as an acid catalyst an...
متن کاملA Facile One-Pot Solvent-Free Synthesis of 1,2-Dihydro-1-arylnaphtho [1,2-e] [1,3] oxazine-3-ones Catalyzed by Nano-Fe2O3
One of the most important goals in medicinal chemistry is the development of new techniques and new heterocyclic compounds with pharmaceutical activity. The present study aimed to use a method for the synthesis of some 1,2-Dihydro-1-arylnaphtho [1,2-e] [1,3] oxazine-3-ones. The question this study tried to answer was this reaction can be performed in present of nano-Fe2O3 as an acid catalyst an...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره شماره
صفحات -
تاریخ انتشار 2009