Scheme 6.
Synthesis of pyrano(2,3b)pyridine analoguesa
R1 = phenyl (20a), cyclohexyl (20b)
a Reagents and Conditions: (a) (i) BuLi, -78 °C (ii). DMF, anh.ether, 31%; (b) R1NH2, ZnCl2, NaCNBH3, MeOH, 49%; (c) 3,4-diethoxybenzenesulfonyl chloride, Et3N, DCM, r.t., 43 – 60%.