Synthesis of 4-aza analog of ramelteon: a novel tricyclic 1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridine derivative as melatonin receptor ligand

The 4-aza analog of ramelteon (-)-1, a novel tricyclic 1,6,7,8-tetrahydro-2H-cyclopenta[d]furo12,3-b]pyridine derivative, was synthesized via the intramolecular inverse electron demand Diels-Alder reaction followed by fluoride-induced desilylation-cyclization. (C) 2011 Elsevier Ltd. All rights reserved.