A SIMPLE APPROACH TO THE 1,3,4,6,11,11а-HEXAHYDRO-2H-PYRAZINO[1,2-b]ISOQUINOLINE SYSTEM
Keywords:3-acyl-1H-isochromen-1-one, ethane-1,2-diamine, recyclization, pyrazino[1,2-b]isoquinolin-6-one, reduction
A straightforward approach to synthesizing the pyrazino[1,2-b]isoquinolin-6-one, which serves as the basis for several biologically active compounds of natural origin, is proposed. In a single step, the interaction of 3-formyl- and 3-acyl-1H-isochromen-1-ones with ethane-1,2-diamine in an aqueous or aqueous alcohol medium leads to the formation of the 3,4-dihydro-6H-pyrazino[1,2-b]isoquinolin-6-one ring. Using the derivative with a methyl group at position 1, it was demonstrated that this heterocyclic system can be reduced to both 1-methyl-1,2,3,4- tetrahydro-6H-pyrazino[1,2-b]isoquinolin-6-one (through the action of sodium triacetoxyboride) and to 1-methyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline (through prolonged heating with an excess of lithium aluminium hydride). A novel method for obtaining 3-formyl-1H-isochromen-1-one (also known as the natural compound Artemidinal) is presented. The proposed techniques employ simple synthetic procedures and inexpensive reagents.
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