Design: mechanism of formation and emerging applications of amino dithio acetal derivatives of pyrimidines and allied nitrogen heterocycles
Subject Areas :
Keywords: Pyrimidines, Aryl nitrile, 1, 2-Dithol, Pyrazinoquinoxaline, Amino dithioacetals, Applications.,
Abstract :
Nitrogen heterocycles have been frequently synthesised and play a pivotal role in synthetic organic chemistry. Pyrimidines are important member of six membered nitrogen heterocycles and have been used as model substrates in a variety of reactions. 2-cyanopyrimidine 1 is an electron deficient aryl nitrile which upon interaction with ethane 1,2-dithol under buffered aqueous conditions afforded amino dithioacetal (ADTA) 2 in excellent yields. However, 2,3-dicyano pyrazine 3 results 4 and 5 when allowed to react with ethane dithol. Pyrazinoquinoxaline is another important member of class of nitrogen heterocycles with inherent properties. A series of dicyanopyrazinoquinoxalines (DCPQs) 9-12 have been obtained when ortho-phenylenediamine 6 and allied compounds were interacted with pyrazine derivatives. A simple and convenient method for the synthesis of quinoxaline derivatives 17 has also been developed from cinnamils 15 in water under reflux/microwave irradiation conditions. This article concentrates on the design and suggested mechanism of different amino dithioacetals (ADTA,s) of pyrimidines, dicyanopyrazinoquinoxalines and allied nitrogen heterocycles. A wide range of emerging applications of these heteroatom compounds have also been discussed.