Scheme 1.
Synthesis of compounds 10a–f and 11a–f. Reagents and conditions: (a) CDI, N,O-dimethylhydroxylamine hydrochloride, NEt3, CH2Cl2, rt; (b) 4-picoline, LDA, −78 C to rt; (c) N,N-dimethylformamide-dimethyl acetal, reflux, then methylhydrazine; (d) H2, Pd/C, ethanol/EtOAc; (e) NBS, AIBN, CCl4, reflux; (f) NaH, DMF, rt.