Structure of Chelerythrine Base

Abstract

The structure of chelerythrine free base was examined. When chelerythrine chloride [1b] was treated with aqueous K2CO3 solution, bis[6-(5,6-dihydrochelerythrinyl)] ether [3] was obtained. An excess of aqueous ammonia under the same conditions yielded bis[6-(5,6-dihydrochelerythrinyl)] amine [4]. The structures of both derivatives were determined by elemental analysis, ir, 1D and 2D nmr, eims, and cims. The formation of an unstable hydroxy adduce 2a (pseudobase) was observed in H-1-nmr experiments only.