An efficient synthesis of 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitriles

作者：Wang, Dao-Lin^*; Wu, Jian-Ying; Wu, Dan; Wang, Yong-Yang

来源：Chinese Chemical Letters, 2014, 25(12): 1555-1558.

DOI：10.1016/j.cclet.2014.07.011

• Benzo[b][1,6]naphthyridine
• 2-Cyanomethyl-4-phenylquinoline-3-carboxylate
• DMFDMA
• Primary amine

Ethyl alpha-(dimethylaminomethylene)-2-cyanomethyl-4-phenylquinoline-3-carboxylate (2) as new synthons directed to 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitriles was obtained by the condensation of ethyl 2-cyanomethyl-4-phenylquinoline-3-carboxylate (1) and N,N-dimethylformamide dimethyl acetal (DMFDMA). Reaction of this enamine with primary amines (3) in HOAc-DMF at 120 degrees C then affords 2-substituted 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitrile derivatives (4) in good yields by a tandem additioneliminationcyclization reaction.

• 出版日期2014-12
• 单位渤海大学