Citation: Dao-Lin Wang, Jian-Ying Wu, Dan Wu, Yong-Yang Wang. An efficient synthesis of 1-oxo-1,2-dihydrobenzo[b][1,6] naphthyridine-4-carbonitriles[J]. Chinese Chemical Letters, ;2014, 25(12): 1555-1558. doi: 10.1016/j.cclet.2014.07.011 shu

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

1.
College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China

Corresponding author: Dao-Lin Wang,
Received Date: 16 June 2014
Available Online: 10 July 2014
Fund Project:

Ethyl α-(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 ℃ then affords 2-substituted 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitrile derivatives (4) in good yields by a tandem addition-elimination-cyclization reaction.
- Benzo[b][1,6]naphthyridine,
- 2-Cyanomethyl-4-phenylquinoline-3-,
- carboxylate,
- DMFDMA,
- Primary amine
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沈阳化工大学材料科学与工程学院沈阳 110142