Synthesis of New Melatonin Analogues from Dimers of Azaindole and Indole by Use of Suzuki Homocoupling

Abstract

N-{2-[3'-(2-Acetylaminoethyl)-1H,1'H-[5,5']) and their analogues in 7-azaindole series (4,5) were synthesized by palladium catalysed reaction starting from indole or 7-azaindole using [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, as catalyst.Melatonin (1), a pineal hormone, plays a major role in the regulation of seasonal cycles and the control of circadian rhythms 1,2 and has been the focus of considerable clinical interest. 3Two human melatonin receptors have been cloned 4,5 and defined as MT1 and MT2 receptors. 6These two receptors belong to the 8 8, PdCl 2 (dppf) Na 2 CO 3 2M 53% for 2 steps H 2 , Ni Raney Ac 2 O, AcONa, 60°C, 4 h 10 2 9 67% 6 866 HETEROCYCLES, Vol.60, No. 4, 2003